This is when a character frequently changes their job to serve the plot's purpose.
May overlap with Honest John's Dealership. Compare Inexplicably Identical Individuals and Recurring Extra, which is a less specific and less likely to be plot relevant version, and The Generic Guy where the character has little relevance to the plot at all. Also compare when a person has a steady job (for now, at least) but who seems to have had insane amounts of former jobs which pertain everything to plumbing for royalty to fighting to unusual research projects.
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Anime & Manga
Touya in Cardcaptor Sakura, since in Japan, "Part-Time Job" (arubaito) is often more accurately described as "temp work" as opposed to a job where one works part time hours. The reason he has so many jobs is because he was only hired to work a particular one for a limited time. In a variation, though, he's the main character's brother and unknown Secret Keeper, as opposed to just being a background joke character with no importance to the plot. Sakura herself comments that her brother holds a LOT of part time jobs, because Touya wants to make and save as much money possible, so he could go to college without being a burden for his father. He also is implied to take them so he can look after Sakura.
He even works in jobs across series — showing up in cameo jobs in Kobato as well as across universes, showing up several times in Tsubasa Reservoir Chronicle at various jobs.
Speaking of Kobato, Fujimoto is another main character who keeps changing jobs — however, he does this to earn as much money as he can to support Sayaka.
She never actually changes job titles, but the waitress from Black Cat works at four or five different restaurants over the course of the series.
A minor character in Suzuka has as many different jobs as she has appearances.
In Rosario + Vampire Capu2, Ruby continues to change what job she's working at the school frequently. One time she's working as a waitress, the next she's helping out the nurse on Measuring Day. She needed something to do ever since her transition from Dark Magical Girl.
Minori Kushieda from Toradora! holds many jobs. She's captain of the softball club, a waitress at a restaurant, a part-time helper at a convenience store... Seems like she is following the advice of someone from a manga...
In Outlaw Star, Aisha Clan-Clan (after being fired from her diplomatic/military position) takes up a rather large number of waitressing positions. Given her tendency to attack people she should be serving, which often results in the whole restaurant being destroyed, it's amazing she can still find work.
One middle-aged woman can be found in almost every episode of Lucky Star, working in a different field every time. Whether it's actually meant to be the same woman isn't exactly clear, though... Especially since one of the later episodes has six or seven of them on screen at the same time.
One of the many reasons Hayate the Combat Butler is skilled and knowledgeable in everything before his current employment, he had to work as a child for his dead-beat parents with a lot of different jobs. He's just got one now, but we hear about his past now and then.
Also, Santa Claus (or someone that resembles him) has been shown to work at various jobs.
Tamami from Chocotto Sister takes on more jobs than she can handle and then tries to let Haruma take the less attractive ones.
Yunyun from Canaan always seems to have exactly the job that will allow her to run into the main cast, which eventually allows her to join the cast in their antics. Subverted, though: she's not doing it just for the money or the thrill, but as The Mole for their enemies.
Could also be a reference to the potential after effects of China's economic growth spurt, as Yunyun mentions that many in the slums take up several part-time jobs to make ends meet.
Li Shenshun from Darker Than Black always happens to be working at whatever place is most plot-relevant at the moment — of course, Li is the civilian alias of the "Black Shinigami" Hei…
Hasegawa in Gintama is either in a brand new job or without one. The explanation is because he is a MADAO. Also because he keeps asking Gintoki & Co. to help him with his jobs.
From Hell Girl, Ai Enma's minions are often shown with different jobs as they observe a prospective client before the string is pulled, except in season three where they all keep the same jobs in a school since they're hanging out with the girl who's supposed to be replacing their current boss.
The cast of Kurosagi Corpse Delivery Service falls into this trope fairly often. Since the filling-the-last-wishes-of-the-dead business tends to be sporadic, they often fill it in with an astonishing array of contract or part-time jobs — from moving tombstones to faking alien crop circles. It's usually the perpetually underemployed trio of Yata, Numata and Karatsu who are seen doing the heavy lifting, but Keiko often turns up in a number of unlikely consulting jobs due to her extremely-rare-in-Japan expertise in embalming. Sasaki seems to be the only one who holds a steady job. Of course, that steady job is selling celebrity gore photographs to fetishists, but hey, it's a living.
Throughout the series, the Landlady of Hidamari Sketch has been shown having a variety of jobs: delivering pizza coupon fliers and temping at the Berry-Mart, along with other, unspecified part-time jobs. She does this so she can keep tenants' rents lower, which is definitely a help to students like Miyako (who has lower rent than the others for other reasons, in addition).
In Fullmetal Alchemist, Psiren, the local Phantom Thief, keeps changing jobs to avoid being caught by the police. The brothers Elric first meet her when she's working in a hospital, then changes to school nurse, nun, etc. This trope is called out by name by Edward when they meet her in her nun get-up: "Why the hell do you keep changing jobs?!"
Tojo from Beelzebub. One possible explanation for his constant shuffling of part-time jobs is because he keeps into trouble when rival gang members show up to fight him.
In Mobile Suit Gundam Wing, Hilde Schbeiker becomes a MS pilot for OZ, a junk dealer with Duo, a spy and a hacker. In the Frozen Teardrop novel, she becomes a nurse, a librarian, an expert in nano technology and a nun.
Donald Duck has done many different jobs. Many of them while forced by Uncle Scrooge to do so. His uncle Scrooge is no slouch either: before becoming rich he did the shoe shiner, the firewood (later peat) seller, cared for cows on the boat that brought him to America, the sailor on his uncle's river boat, river captain, sailor again, cowboy, a brief stint as a sailor on the Cutty Sark, an actor for the Wild West Show (according to Buffalo Bill, Scrooge actually came up with the idea!), the prospector, another stint as a sailor to pay the travel for Klondike, and the prospector again. After becoming rich he did the banker, directed a sawmill, armed ships, SOLD LEMONADE, and traveled the world to create and buy companies, mines and other things that would make him richer (including the ENTIRE STOCK MARKET in 1929), before settling in Duckburg. And I probably missed a few jobs...
Big Nate has "School Picture Guy", who when not the photographer has shown up as a clown, a reporter, etc…
Hieronymus Jobs in one story by Wilhelm Busch. (He's just the 18th century equivalent of a spoilt upper class son.)
Dogbert from Dilbert is definitely this. In a single anthology that ranged from the 5/19/91 strip to the 12/13/92 strip, Dogbert had no fewer than forty jobs: a teacher at "Dogbert’s School of Hard Knocks," a business consultant, an encyclopedia writer, a tabloid newspaper writer, Dilbert’s lawyer, the manager of "Dogbert’s Find-A-Friend Service," a pop psychologist and lecturer, a used car salesman, the despotic king of Elbonia, the host of "Dogbert’s World of the Unexplained," a Supreme Court justice, a prophet, a newspaper critic, a babysitter, the warden of a private jail for the rich and famous, an insider stock trader, a square-dance caller, a Presidential candidate, the host of "Dogbert’s World of Amazingly Ignorant People," a tax preparation accountant, an industrial spy, an economic advisor in Washington, a MTV reporter, a greeting card designer, an advertiser, the host of "Healing for Dollars," a teacher at "Dogbert’s School of Common Sense," a newsletter writer, a marriage counselor, the leader of a vegetarian movement, a hitman, a private detective, a demagogue and author, a hypnotist, a doctor, the manager of a dating service, a time management expert, a driving instructor, a teacher at "Dogbert’s School for Jerks," and the Supreme Ruler of the World. He also ran a "Pet Me" stand, an "I Will Listen to Your Sad Story" stand, a "Confess-O-Rama" stand, and a "Parent Licenses" stand.
Arguably Dogbert still only has one job, Con Man, and these are basically scams he runs.
Also, Ted. He's been fired twice, quit twice, and even arrested once.
Condorito constantly changes jobs in most of his appearances. In his 70's apparitions he had a stable job in a garage/car wash unless it was needed to be otherwise for the sake of a joke, but this started to quickly fade out of use when the comic started to rely more and more in the creation of different worlds to make the jokes work. Sometimes Condorito is the major of a rural colonial Pelotillehue, and others a hobo in a huge Pelotillehue metropolis.
A humorous InuYasha fanfiction has Sesshomaru. As Kagome and crew travel to all fifty of the United States. Any time they stay in a state for any length of time, they will find Sesshomaru has a job there relevant to what they are currently doing. The author even encourages people to spot how many times he pops up. The only time the group ever arrive anywhere before Sesshomaru, it was because they ran him over on his way to work. Story can be found here. Roadtrip Around the USA
It looks like the fatal flaw in their plan is usually the attempt to integrate Wallace's fundamental inventorship into the new job; it seems like everything Wallace invents is useful for the plot of the feature, but once they've saved the day, the market dries up. If they wanted a stable job, they should look at what the neighborhood is in constant need of, and then invent something to deal with that. But then there wouldn't be any more plots.
This is continued in Wallace & Gromit's Grand Adventures, where Wallace starts up an ice cream business, a detective agency, a beekeeping business and a seaside resort — the latter two operating out of his cellar.
Films — Live-Action
Bert in Mary Poppins goes through several jobs and street performances in the course of the film: one-man-band, pavement chalk artist, chimney sweep, kite seller. He also mentions selling hot chestnuts, though we don't see him doing it. This follows the books, in which he is a jack-of-all-trades. The chimney sweep is a separate character, but they just added it to Bert's repertoire for the movie.
Che, in the film adaptation of the Webber/Rice musical Evita, appears as a waiter, valet, projectionist, student protester... indeed in just about any capacity other than Marxist icon Che Guevara, who was the narrator and Deadpan Snarker in the original stage version. In contrast, the film's Che (no last name) is not only a Lemony Narrator but also The Everyman.
Ramone in The Proposal is seen as a waiter, a stripper, a store employee, and a priest at a wedding. Possibly justified in that it's a small town....
Gordon Urquhart in Local Hero is an innkeeper, lawyer, town mayor, and drives a cab during the busy season due to living in a small town.
Chico's character in A Night at the Opera. "[You thought I worked at] The circus? That was ages ago. Last week. I have lotsa jobs since then."
In Brain Donors, the character played by Mel Smith is not only a cab driver, but also cleans swimming pools and runs his own toupee business. In fact, he's only driving the cab as a sideline. As soon as he gets his drivers license, he's out of there.
Name all the jobs The Three Stooges have had. It may take a while. Granted, during the Great Depression, quite a few of the occupations were "vagrant", "drifter", "bum", and "none".
Bruce Campbell's unnamed character moves upwards in society through the Spider-Man Trilogy. In the first movie he's a wrestling announcer, in the second he's an usher at a posh theater, and in the third he's working at a fancy French restaurant (speaking with an awful fake accent).
Shawn Ogg in the Discworld novels set in Lancre is, among other things, the captain of the guard, its standing armynote Except when he's lying down, the Royal Historian, a footman, the postman, and the conductor of the Lancre Light Symphony Orchestra. But his most important job is cleaning the privies. You can do without a Royal Historian for a week, but if the privies haven't been cleaned, you'll know about it.
Cut-Me-Own-Throat Dibbler is another prominent example. Sure, he inevitably returns to his primary business of selling what are technically sausages "inna bun", but whenever a new industry begins to form in Ankh-Morpork, you can rest assured that Throat will try to cash in on it. All while employing the same level of quality control that he does with his sausages.
Ponder Stibbons, the Only Sane Man at Unseen University, keeps acquiring new job titles and duties simply because no one else wants them. By Unseen Academicals all those titles give him a majority vote on the University Council, meaning he's technically the most powerful person in the entire university.
In Star Wars: Knight Errant this become a plot point: the Protagonist Kerra Holt slowly discovers how not one, but several bystanders change their occupations during the brief stay at Arkadia's base of operations. She eventually discovers that inhabitants are constantly rotated between absolutely different positions on a completely random basis: it serves the Sith purpose in a pretty twisted way.
The father in The Swiss Family Robinson spent "a large portion of his childhood" in the workshops of pretty much every craftsman known to man. Admittedly he doesn't say he was working with them, but he had enough exposure to each to recreate their machinery from memory.
On Barney Miller, Det. Arthur Dietrich had the question asked of him when he threatened to quit over a dispute with the Police Commissioner. His squad members listed all the other occupations that Dietrich had attempted and abandoned (including lumberjack and beekeeper - his "wilderness period") and convinced him he was just making an excuse to quit yet another profession.
In Monk, it's revealed that Natalie Teeger is a walking example of this trope, having bounced from job to job before working for Monk. Some known occupations have included a temporary job at a mall, a stint in a regular office, and a Vegas blackjack dealer.
Frank Nelson played an omnipresent clerk who gave Benny trouble across multiple industries. At one point it was lampshaded in the quote formerly at the top of the page.
Jack Benny: You again!! Every time I met you, you have another job! You're my waiter, my bellboy, my shop clerk! Now you're a lawyer?!? Frank Nelson: Well, at least I am trying to better myself in life, what's your excuse? — The Jack Benny Program
(The role originated on the early radio show.) He was identifiable by his bald head, mustache, and Catchphrase "Yeeeeeeeees?" Nelson played this same role on many other shows including I Love Lucy, Sanford and Son, and even a Garfield special. After his death, a similar character showed up on The Simpsons, explaining his odd cadence with "I had a stroooooooke!" The Simpsons character even has, in one episode, a Brazilian lookalike who says, "Siiiiim?"
Jack Benny's show also brought us Mr. Kitzel, who started as a hot dog vendor but eventually took on all sorts of random jobs.
The episode of the Jack Benny program quoted above was a dream episode where Benny is on trial for murdering a rooster. He hires Perry Mason (Raymond Burr himself) to defend him but he is roundly beaten by Nelson.
In the Get Smart episode "The Tequila Mockingbird", Valdez is the mayor of Miraloma, Mexico — as well as the Chief of Police, superintendent of schools, coroner, librarian, dogcatcher, city clerk, justice of the peace, tax collector, the saloonkeeper, the head of the tourist bureau, and the town torturer.
"I wanted to talk to the head of the tourist bureau." "Who told you I was head of the tourista bureau?" "Uh, the proprietor of the saloon told me." "I did not!"
Sgt Joe Friday and his various partners turn up in just about every police division, from Bunco to Citizens Complaints, on Dragnet.
Kirk from Gilmore Girls. It is eventually lampshaded when out of the blue, he overbids Luke in a real estate deal:
Luke: Where the hell did you get that much money? Kirk: I've been working for eleven years. Luke, I've had fifteen thousand jobs.
He also doesn't seem to have a place to live, as seen as one episode where families in Stars Hollow "take turns" hosting Kirk while allowing him to babysit their children. (Though he seems to act just like one when he stays at Lorelai's house.)
Minor flashback character Randy Nations on LOST has been seen as Hurley's boss at Mr Clucks' Chicken Shack, then Hurley's employee at the Chicken Shack, then Locke's boss at the box company, and most recently an employee at "Circuit House".
There's a bit of Fridge Brilliance at work here: Hurley bought Mr Clucks after winning the lottery (keeping Randy on as manager) but it was short-lived because the restaurant was hit by a meteorite. Attributing this event to his streak of bad luck, Hurley felt bad about losing Randy his job and got him a position at the box company he owned, where Randy proceeded to act like an even bigger Jerkass knowing that he had protection from on high. When Hurley was presumed dead in the plane crash, karma hit Randy square in the ass.
Locke qualifies as well: box company, toy store, hippie, home inspector, shaman, MacGyver...
In Star Trek: The Original Series, one crewman (Lt. Leslie) filled a bewildering number of jobs aboard the Enterprise. He has been a security guard, helmsman/weapons officer, navigator, medtech, bridge crewman, technician, engineer and transporter chief.
This is actually true of allred shirts on TOS, though none have been quite so prolific as Leslie. Only one redshirt (Lt. Kyle) has a consistent job (transporter chief), and even he was seen pinch-hitting at the science station and the helm. (In his cameo in Star Trek II, he is communications officer for the Reliant).
Between The Next Generation, Deep Space Nine and his back story, Miles O'Brien has been a tactical officer, flight controller, security guard, a transporter chief, tactical officer again (briefly), one of the greatest engineers in the galaxy, and then moves on to teaching at Starfleet Academy. Not a bad career path for an enlisted man.
Fellow Transplant Worf has been communications officer, security chief, tactical officer, ambassador, lawyer (okay, that one's sorta cheating. He played his identical and identically named grandpa in a TOS movie.) and back to tactical whenever crossing back over for the TNG movies, and when Data was thought to be dead, Worf was the one who was going to get his jobs, too (meaning he'd have been doing his, Tasha's, and Data's jobs all himself at once had Data's death been for real.)
In the Star Trek Novel Verse, he's promoted to first officer of the Enterprise (which likely would've been Data's job had he not died in Nemesis).
Star Trek: Voyager. Out of sheer need and a desire to be useful (so the nice people don't kick him off) Neelix has been a jack of all trades. Morale officer, cook, diplomat, babysitter and much more as the plot calls for it. His background had given him a deep understanding of these jobs.
He's actually totally incompetent at most of them. His survivalist skills get people killed the one time they try to employ them, no one but his girlfriend can stand his cooking (and he once crippled the ship with cheese), and as morale officer he's so annoying that Tuvok tests his control in "Meld" by creating a hologram of Neelix and timing how long it takes for him to strangle the little rodent to death. They let him keep them because no-one else wants to.
More successfully, because there are people who would not watch him die with a broad grin and he seems to actually know a few things about anything, Tom Paris is the Officer In Charge Of Everything. He's an ace pilot, engineer, negotiator, and transporter chief, and his training in biochemistry has made him the official nurse as well. Because obviously in a situation where you need a nurse there is no possible way you could also require a pilot.
Poor old Helo. He gets shoved around from job to job regardless of his actual rank. He's actually a trained Raptor copilot, so his job is to sit in the back, play on a computer and get bossed around by his pilot. But during the course of the series he ends up as second-in-command to Galactica itself, caretaker to a community of refugees, and even CAG - commander of all Galactica's fighters and Raptors, despite no evidence of him being able to fly anything himself. "Copilot" implies actually having piloting skills, since the primary function of a copilot is to act as a backup pilot when necessary. We see Helo piloting a Raptor during the assault upon the Resurrection Hub. Much like the real-world US Navy aircraft carrier commanding officers, it seems that Colonial officers aren't eligible for command unless they have some amount of stick time in a cockpit.
Lee Adama started as a Viper pilot visiting from another ship and was promoted to Galactica's CAG by the end of the miniseries. Since then, he's had a number of jobs, including military advisor, Raptor pilot, military police, battlestar commander, lawyer, Quorum representative, and even president of the Colonies on various occasions. Sometimes he's held several of these positions at the same time. Lampshaded in one episode during some argument with Tom Zarek saying, "Excuse me, I'm confused, but what exactly is your job this week?"
Major Marks, recurring character in the Stargate Verse, has been an officer aboard all five of the Air Force's star ships over the course 3-4 years of three shows. No explanation has been given for his frequent transfers, and in one instance he might have been in two places at once.
Xander in Season 4 of Buffy the Vampire Slayer had a new job in just about every episode. This was the season where his friends went to college and he was trying to find himself. Eventually, he settles into a construction worker.
Mr Pitt appears in The Beiderbecke Affair and each of its two sequels, having taken what he describes as a 'sideways career move' each time.
This is Shawn's entire background before forming the eponymous detective agency in Psych. He seems willing to keep this up if it helps the case, too, as when he took a job at the museum in "From the Earth to Starbucks."
In Disney Channel's Wizards of Waverly Place, a woman appears in some of the episodes of the first two seasons, sporting a new job, and it's not like she only does normal jobs either - she also appears at the Wizarding School. She is easily identified through her monotone voice and short, dark hair and always seems to hate whatever she is doing for that episode.
After being fired from Shortywood on an episode of Pit Boss, Ronald switched jobs constantly. He did get his old job back, though.
In the last season of The A-Team, Murdock is released from the V.A. Hospital to be with his friends, and this becomes his gimmick for every episode.
Henry on Eureka, complete with a different Velcro patch on his uniform for each of his jobs. In season 3, he gets a "Mayor" patch. He doesn't actually switch jobs a lot, he holds multiple jobs at once due to his expertise in many areas.
A Running Gag in Austin & Ally is that Trish gets, and gets fired from or quits, her job each episode. She even had a Catchphrase of "Guess who got a job at the...?" This joke seems to have been retired for the third season.
Nick on My Family had a new job in almost every episode. On one occasion, he was able to afford a motorbike because he'd been saving up the severance pay every time he was fired. Later in the series, Abi went through a large number of jobs as well.
Jeffrey of Monmouth in Merlin. His official title is "Court Genealogist", but he also runs the library and (even more oddly) officiates various court ceremonies, like crownings.
Kramer from Seinfeld doesn't really have a designated job, but he is regularly seen taking on odd jobs or getting caught up in various get rich quick schemes. A last-season episode revealed that he has technically been on strike from his bagel store job for the entire run of the show, and he managed to get himself fired immediately after going back.
The 60s-70s Brit ComThe Worker may count as a variation. The title character, played by Charlie Drake, can never hold down a job for more than one episode, but his reason for getting fired is never the same twice.
Wrestlers often go through many personae in their career. Newer wrestlers may be given gimmicks related to cover up their relative lack of experience, and older wrestlers may be given them to cover up declining skills. Sometimes, it's to give a wrestler a change of pace when one characterization has become stale.
In the mid 90's, a common trope was the Wrestling Professional. One of the classic examples is Thurmond "Sparky" Plugg, later Bob "Spark Plug" Holly, who was a wrestling race car driver. Also around at the time, T.L. Hopper, the wrestling plumber, Duke "The Dumpster" Droese, the wrestling garbage man, and The Big Bossman, the wrestling prison guard. Most of these characters can safely be called WrestleCrap.
John Cena, after debuting was directionless until management saw him jokingly rapping back stage. His first major character in WWE was as a white rapper in the vein of Vanilla Ice. While his freestyle raps were later abandoned, vestiges of this character are seen in his current ring persona.
These job changes can be dramatic. In the early 2000's The Undertaker took a turn from an undead, supernatural zombie character to a brutal biker, still called The Undertaker. He later returned to the "Deadman" gimmick due to negative reaction to the "Bikertaker".
The undisputed king of changing jobs in professional wrestling is Ed Leslie, most well known as Brutus "The Barber" Beefcake in WWF in the late 1980's. As a close friend of icon Hulk Hogan, he was always given preferential treatment, despite a relative lack of skill. To keep him at the front of people's minds, his character changed frequently. Some of his other gimmicks included "Brother Bruti", a fanatical follower of Hogan, and "The Bootyman", a Lothario. He in total has kept about 10-12 different on-screen characters, far more then most wrestlers do in a career.
This became part of Mick Foley's persona, late in his career: At various times, he had been the Psycho for Hire Cactus Jack, Surfer Dude Dude Love, and Psychopathic Manchild Mankind. Foley played them off less as jobs than as alternate personalities, culminating in a memorable Royal Rumble where Foley competed as all three of his personae (He got eliminated as Cactus Jack, went back stage and came out as Mankind, and later returned as Dude Love).
Grover on Sesame Street. His most well-known position was as a waiter at Charlie's Restaurant, opposite the Blue Man, and even these expanded into a wider variety of spots — as a hot dog vendor, a taxi driver, elevator operator, etc. — all thoroughly incapable of satisfying his one recurring customer.
In the '70s Grover frequently appeared as a door-to-door salesman, usually calling on Kermit the Frog. Each time he'd be peddling a different item, and always something a frog would have no use for: earmuffs, toothbrush, nose warmer, etc.
Round the Horne: Julian and Sandy tried a new job every week while waiting for their acting careers to pick up. The standard set-up for their sketches was for Kenneth Horne to enter a shop or some other place of business and be unexpectedly greeted by Julian's catchphrase. "Oh 'ello, I'm Julian and this is my friend Sandy."
Hancock's Half Hour had an unnamed character the writers called 'Snide', who has a different occupation in every episode he appears in. The minute Kenneth Williams (who also played Round the Horne's Sandy) coos " 'ello", the audience burst out laughing, anticipating Tony's horrified reaction.
In Gilbert and Sullivan's The Mikado, the character of Ko-Ko is the Lord High Executioner. The character of Pooh-Bah is "The Lord High Everything Else". At the most extreme he changes jobs six times in one paragraph twice in the course of a single sentence.
Of course, as First Lord of the Treasury, I could propose a special vote that would cover all expenses, if it were not that, as Leader of the Opposition, it would be my duty to resist it, tooth and nail. Or, as Pay master-General, I could so cook the accounts that, as Lord High Auditor, I should never discover the fraud. But then, as Archbishop of Titipu, it would be my duty to denounce my dishonesty and give myself into my own custody as First Commissioner of Police.
A rather creepy version is the baritone guy in Death in Venice, who appears in seven different forms and jobs. It's the same singer, and, well, most likely a symbol for This guy.
The appropriately named Common Man in A Man for All Seasons fills all the various minor odd jobs in the play.
In Our Town, the narrator himself appears in the play several times, each time having a different job.
The Teenage Mutant Ninja Turtles toys would often include the turtles in various jobs such as soldiers, spies, samurai, emergency services etc. Those jobs make sense considering the turtles' heroic nature, but when you have Surfer Michelangelo or Rock Star Leonardo, it's getting out of hand. If you watched the 80s cartoon, Surfer Michelangelo would be far more likely than soldier or spy!
Namingway from Final Fantasy IV DS. He finds his calling 17 in-universe years later in Final Fantasy IV: The After Years, however, as the Challenge Dungeon Manager. Rather hilariously, every time he changes his job, he also changes his name. So in effect, he's still fulfilling his original purpose (changing names), but only for himself.
Stan from the Monkey Island series is running a different business in each game. In order, they are: used ship salesman, used coffin salesman, life insurance salesman, time-share representative and attorney-at-law-who-makes-a-side-income-by-selling-souvenirs-based-on-his-cases. His job changes are often explained as a result of something that Guybrush did in the previous game.
Sybil Pandemik from Telltale Games' Sam & Max adventure games. She has a different job in every episode of Season One, and each of them is coincidentally useful in solving the case.
Well, almost all of them, she's already been through about 3 or 4 jobs by her first appearances. By the end of Season One she's been: interior decorator, taxidermist, tattooist, psychotherapist, tabloid journalist, professional witness, dating service, carbon-dating service, beta tester, and Queen of Canada. In Season Two she uses her office for other purposes, such as choosing a new boyfriend and planning her wedding, though she doesn't do anything commercially.
All throughout Season Three, whenever you meet someone new (at least for that season) it takes a snapshot of them, and provides (usually) three "useful" facts about them. When Sybil shows up, it shows "former Psychotherapist, Former Brain Surgeon" and trails off the screen. You can hear the amount of jobs she's had speeding up and continuing to list past the screen!
Sam refers to it as "Attention Deficit Career Disorder", or something like that, which is an apt name, as with each career change, Sybil gushes about how convinced she is that she's finally found her one true calling.
Larry Butz constantly switches jobs between cases, usually to get closer to his latest girlfriend. By the end of the first three games, he seems to have found his knack in painting. It doesn't last.
Wendy Oldbag, meanwhile, is a security guard in a different venue every time she shows up. The first time it's justified — she snipes at Phoenix about how Global Studios fired her following the first game. Although in Investigations she seems to have taken a part time job wearing costumes for Gatewaterland. Edgeworth wishes she'd kept the mask on.
Maggey Byrde is more or less forced into this due to her bad luck.
Mona from WarioWare has been a gelato server (original), a pizza delivery girl (Twisted), a rocker (Touched), and a cheerleader (Smooth Moves), and she even develops microgames on the side. She Must Have Lots of Free Time.
Given her appearance (and that cheerleader part at the end), some players think she's a high-schooler jumping between part-time jobs.
Squicky that she's clearly Wario's love interest, then. Or at least a cosplaying fangirl.
Not to mention that in Smooth Moves, she's not just a cheerleader in her level, but also a steamed bun vendor in Young Cricket and Master Mantis's level.
In Game & Wario, she's a news reporter.
In Psychonauts, you meet a mysterious Almighty Janitor occupying various jobs in various locations. He turns out to be the legendary superspy Ford Cruller, the commander of the Psychonauts, and it later turns out that his mind was shattered into fragments in the past. Despite appearances he's not merely keeping an eye on things with his different jobs, each one is a different fragment of his mind.
A good deal of the Super Mario Bros. cast. To date, Mario alone has been a carpenter, a plumber, a doctor, a demolitionist, a grocer, a pizza delivery man (in the Donkey Kong record album), a kart racer, and a toy maker, on top of constantly rescuing Peach from Bowser.
And all that is if you don't count referenced cameos in games not specifically mentioned as something involving the Universal-Adaptor Cast. He's also played baseball (Baseball), golf (Mario Golf), soccer (Mario Strikers), refereed and played tennis matches (Mario Tennis), and even worked the count in the boxing ring (Punch-Out!!). This might explain why Mario holds the record for most appearances in a video game.
Funky Kong in Donkey Kong Country has been a plane/helicopter salesman, ran a boat hire firm in the third game, ammunition/weapon maker in Donkey Kong 64 and racer in Mario Kart!
Less of a reach, though, as all of his DKC services involve building and subsequently selling/renting machines. As for Mario Kart, just about everyone in the extended Mario universe seems to do that (presumably he built his own karts.)
In No More Heroes, protagonist Travis earns his money in both games by doing every job imaginable, however, his boss in each job is always the same. It probably has something to do with "the unspoken laws of Santa Destroy" he keeps babbling about.
Fallout 3: "Name's Lucas Simms. Town sheriff. And mayor too...when the need arises."
Bea Bear from the SPY Fox series. The game Operation Ozone had her explain why she changed jobs.
Sheep Man in Mega Man 10 originally herded sheep; he was built for that purpose. He got bored and worked to test static cling at a textiles factory. He grew bored of this too and was about to change jobs once again when he was inflicted with Roboenza and went berserk.
The radio stations for the Grand Theft Auto series almost always include Lazlow Jones hosting at least one segment of a station - the explanation being that, within about two decades, he's been fired from six stations across three different states.
Bubs of Homestar Runner can always be found behind the counter of his concession stand, but what goods and/or services he has available at the time is often plot-dependent. This could be seen as him just being an opportunist and spontaneously catering to whatever need the others happen to have at the time (regardless of whether or not it's within his areas of expertise), but notably he once switched from selling "questionable medical insurance" to selling donuts before it came up as a plot point. And was very upset when it turned out to be one, in the form of Homestar also setting up a donut stand about five feet away.
And Senor Cardgage, who has been, so far, a mortgage consultant, a used car salesman, an "Intregway" seller, author of "The Homeless Romantic", a movie theater usher, and (probably creepiest of all) a daycare owner.
Many characters in Happy Tree Friends have been seen with various jobs, but Lumpy is definitely the worst offender. He's been a farmer, surgeon, carol singer, etc.
Achewood's Ray Smuckles sees a business opportunity around every corner, from Williams and Sonoma Erotic Fiction to machine rolled marijuana cigarettes.
Real Life has this with Alan Extra, who is basically anything from a pilot to a movie theater worker, to a random guy on the street who gave the main character directions.
In fact, one of the comics states flat out that Alan Extra is everyone who isn't a named character. Store Clerk? Alan. Tech Support? Alan. Guy in panel 1 who looks different from guy in panel 4? Both are Alan.
Vess MacMeal from Platypus Comix first appeared in Keiki comic, as a spokesgirl for a blackmailing service. She later starred in her own comic, as a teacher. Today, she runs a Q&A column in Portland, Oregon periodical BANG! The Entertainment Paper, and claims to have many other side jobs. Incidentally, her name intentionally sounds similar to that of Tress MacNeille, who voiced Lindsay Naegle, the Simpsons character who inspired this trope's name.
The Yurble Janitor/Foreman/whatever outfit he's shoved into next plot in Neopets.
Played with in The Joker Blogs: the Joker recruits a homeless man named Ted to help film his exploits. Over the course of about half an hour (if that), Ted claims to have been a cameraman for the news, a priest, a medic and a delivery man. It's unclear if he's desperate to sound useful or just off his nut.
Or he could have actually been fired from all those jobs. He didn't say he was good at any of them.
Season 2 confirms that he was at least telling the truth about being a GCN cameraman, and that he was married to Summer Gleason while employed there.
A running gag with Kanoko on Gaia Online was her constant short-lived attempts at employment in various Chance Item storylines. Eventually she managed to find long-term work as a shop assistant at two shops, but she still applied to be a Halloween mascot the next year, which led to a Lampshade Hanging.
So, for Halloween, I was thinking sort of a cute, elegant... wait, why am I still looking for a job?
Ben Schwartz's character on Jake And Amir never appears with the same occupation twice. Thus far, he's shown up as a dating coach, a couples therapist, a private eye, a painter, a mountain hiker, an interrogator, a milk man, a doctor and an usher.
Mocked in The Nostalgia Chick's review of Jem: the Jem dolls might just be a blatant money-making fad, but at least she knows what she wants to do with her life, while Barbie (see above) seems to have ADHD or something.
So far, the Ugly Old Hag (from Shaggy Dog Stories) has been seen running a trap store, a video rentals store, a pet shop, and an 'Authentic Italian Cuisine' stall.
American Dad! provides us with Officer Turlington, IRS/Spa Inspector/ Officer of Internal Affairs, who usually shows up in his plot-related episodes to give the characters a really good, in-universe Mind Screw. As it turns out, he's just having a hell of a difficult time with his personal life as do the Smiths with their criminal activities, as demonstrated in the episodes "Meter Made", "Live and Let Fry", and "Chimdale".
In an episode of Foster's Home for Imaginary Friends, Coco takes several jobs at the local mall that end up relating to what the other main characters are doing. It is later revealed she saved up for a massage chair for Madam Foster's birthday.
Troy McClure is an extremely prolific B-Movie actor.
Lindsey Naegle is a single successful businesswoman/TV executive. The season 13 episode "Blame It On Lisa" lampshaded this when Marge asks Lindsay why she keeps changing jobs. Lindsay's answer: she's a sexual predator.
The very point of the character Gil is to be perpetually dangling by a thread at his current job, whatever it may be — one episode he was in real estate, another had him working at a shoe store, another was at a car lot, and another had him as a department store Santa.
Captain McCallister has held a lot of nautical jobs (despite not being a licensed captain), as well as owning and operating an all-you-can-eat seafood restaurant (the latter of which has been used more often in later episodes).
Squeaky Voiced Teen (whose name was established as Mitch Peterson early on, then seemingly forgotten by the writers) either works at Krusty Burger or works as a ticket taker, concession stand clerk, or usher at the Aztec Movie Theater (or the Googleplex). Some episodes have him working at an ice cream parlor called Phineas Q. Butterfat's.
A mustached Charles Bronson-sound-alike known to fans as "Sarcastic Middle-Aged Man" (also known as Wiseguy) is a customer service worker. Sideshow Bob calls him "Raphael" in one episode, but his name has never been used since. The following exchange occurred in "How I Spent My Strummer Vacation" with Homer in Sarcastic Man's taxi:
Sarcastic Man: So, what do you do for a living? Homer: Oh, you know, I'm a guy at a place. How'd you get such a crappy job? You a convict or a junkie? Sarcastic Man: Little of both.
"Bart Sells His Soul" features two mustached "Sarcastic Middle-Aged Men". One working as a bug exterminator at Milhouse's place, the other driving a street cleaner car, running over Bart's car; then driving it down a subway station staircase.
That Jerk Who Says "Yeeehs?" is an homage to Frank Nelson, above.
Homer Simpson. From the perspective of any other person in Springfield, he must be yet another "that guy who's doing something different every week". This is lampshaded when Homer (while talking about his latest job) says "I've been a ..., but I've never been happier than I am now." The ellipses comprised every career he'd had to that date (including things that aren't really jobs, like homophobe). In the time it took for him to list them all, Marge had enough time to put curlers in her hair.
Sal the heavily's-accented New New Yorker. Considering it's The Future, the creators haven't made up their minds whether there's one Sal who can't hold down a job or a cartload of identical clones. Why, precisely, one would clone a slovenly, ill-mannered customer like Sal is a riddle for the ages.
This is the same universe that creates (and presumably programs) robots with the capacity for substance abuse and laziness. Cloning a guy with a bizarre verbal tic and a bad attitude is par for the course. Considering that one of his jobs is artwork (apparently in the 31st century all fine art is tattooed on fat guys, and Sal claims to be on loan from the Lourve) it's possible that his characteristics are considered valuable.
At least once, Sal had two different jobs in the same episode and was acknowledged to be the same guy. At the beginning of the episode, he's a truck driver. Later on, he's a construction worker, but he and Fry recognize each other from the truck stop.
Abner Doubledeal has appeared in three episodes — each time as a Corrupt Corporate Executive bent on manipulating one of the main characters, but also each time in a different field. First he owned a pro wrestling promotion, then he owned the New New York Mets, then he was a TV exec.
There's also the Grand Midwife from Kif's homeworld. She's also the Grand Priestess, the Grand Lunch Lady, the Grand Funeral Director, and the Grand Butterfly Curator. When Fry recognized her in her second appearance, she explained that she works five jobs. Each of them grand.
Chuck and Leon, better recognized as The Chameleon Brothers. They're always on the hip end of any career, often as entrepreneurs or artists, and have an extremely fake Scandinavian accent. Their Funny Animal species is a dead giveaway to their ever-changing role.
One main character, Filburt, was given a couple episodes as a WDYKCJ before being promoted to a main major character. Another character, Dr. Hutchison, held a number of jobs in various medical fields before being promoted; upon meeting Dr. Hutchison, Rocko would invariably say, "Dr. Hutchison? I thought you were a [dentist/pharmacist/whatever job she had last]", to which she'd respond with laughter and a pun relating to the previous job: "I couldn't handle looking down in the mouth anymore!" (One time, Rocko just said all the jobs at once, to which Hutchison replied, "Yeah... it's been a crazy year.")
Rancid Rabbit of CatDog is a fairly untrustworthy example of the trope, seemingly filling every authority position on the show. In one episode, he appears as both a teacher and a policeman. Cat is a bit surprised.
In one "Cow and Chicken" episode, Red Guy himself ends up in jail, and meets the warden — who, as pointed out, looks exactly like him. Sadly, this was the end of the episode, so the gag didn't go any further.
Uncle Ruckus on The Boondocks. At first, it seemed he just couldn't keep a job for very long, considering his personality, but a look into his private life showed he really works about thirty jobs simultaneously.
He has 47 jobs including Gravedigger from 2AM to 7AM
Kim Possible: Mr Barkin seems to be the substitute teacher for every subject, coaches the football team, works part-time at Smarty-Mart, and is leader of a troop of Pixies (a Girl Scout analogue). This is lampshaded in an episode where they meet Mr. Barkin's father who works at a Living History community. The senior Barkin holds every single occupation in the village by himself, including churning butter. In a dress.
Bruce, the effeminate guy with a mustache in Family Guy is usually holding a job, that usually ties with his "bleeding heart liberal sensible" persona. He's been a teacher, a faculty worker, a host for AA, a psychic, a lawyer, etc.
Peter is an aversion, changing jobs during the show's run, (including stints as a safety inspector at a toy factory, a self-employed fisherman, and a shipping clerk at a brewery)- but all have been addressed logically in the plot and he never comes with a new job out of nowhere- except in random flashbacks, though many of those are nonsensical, such as "providing night-time heat for Lara Flynn Boyle", or, "acting as Sandy Duncan's glass eye".
Doubly so since the creators want to have him change jobs every couple of seasons since this is the common case in Real Life.
Santa Claus in Pucca. He's had A Day in the Limelight episode or two, but he's mostly there to be whatever strange job is needed, from ticket taker, to "guy in a frog costume." Since he only works his well-known job one day a year, he seems to have a lot of hobbies and side jobs.
Jeremy always has a job nearby what's going on in Phineas and Ferb, usually at a concession stand chain in the series.
Literally everyone on The Mr. Men Show, most notably Little Miss Whoops, who can't keep a job because she's just so bad at everything she does, despite always claiming to be "a trained professional".
One episode revealed that the Mr. Men and Little Misses invoke this trope deliberately, getting new jobs every Tuesday.
Mr. Swindler of Garfield and Friends has a number of jobs over the course of the series. He usually only changes jobs once in each episode he's in (the main job in which his subpar workmanship during most of the episode puts Jon off his business for a while, and the job that pops up in the last few seconds when he offers his services and they run away screaming), but in a notable exception, he had a series of home repair jobs. During each job, he set up the next job by causing a new problem. Eventually, Jon is exasperated into selling his house for a pittance. Garfield scares out Mr. Swindler by pretending to be a ghost, but he soon returns in ghost hunter gear... In one episode, Garfield says, "Aren't you the same guy in every episode?"
While on the subject of Garfield, in Garfield in Paradise, suspiciously the same person who looks suspiciously like Frank Nelson is both a hotel clerk and a car rental agent.
Nelson-type man: (as the rental agent) Yeeeeeeeeeeeeehs? Jon Arbuckle: You look familiar. Nelson: I have a brother in the hotel business. Garfield: Racket is more like it.
Meeker and Snurd from Bobby's World all constantly reappear with different jobs ranging from pee-wee sports coaches to Airport Security personnel. The Generics always act like they've met for the first time.
Jim Moralčs from Code Lyoko may have a stable job now, but he's had a ridiculous number of jobs in the past, 21 in total, from sewer worker to basketball star to locksmith to B-Movie actor to professional ping-pong player. This all in addition to 20 years as a gym teacher at Kadic. Every time someone brings up one of his old jobs, he tells them that "I'd rather not talk about it." The catch phrase became the name of an episode, in which Jim gives the kids a run-down of some of his old jobs. Though there always seems to be some truth in these jobs, he still tends to embellish his exact role.
Jonesy, a character from 6teen, has a running gag of being fired Once per Episode. He's also a main character, which is a tad rare.
One episode shows he has a resume consisting of some thirty pages of work history. He says this should help him get a job, but his friends point out he's never worked anywhere for more than a day. The sheer ridiculous size of the mall contribute to this.
According to Word of Jude, if Jonesy had been able to work at Stick it before it was closed due to health reasons. Jude would had fired Jonesy for sticking the wrong meat in the wrong stick despite their friendship.
Jimmy Witchard the violent brain-damaged man from King of the Hill has a different job nearly every time we see him, a concession stand manager, garbage man, janitor, amateur artist, etc.
The first two seasons of Rugrats featured a pair of teenagers named Larry and Steve who would be working a job of some sort only to have the babies cause them to mess it up. Of course, the fact that they kept messing up their jobs no doubt explains why they kept changing them.
In the original The Flintstones series, Barney is never shown with a consistent job, though in later specials and series he is often shown working alongside Fred at Mr. Slate's quarry.
The gag credits for the first season of Animaniacs listed Kathryn Page as a different nonsensical crew member. These may all be part of her "real" job as one of the interns, as shown in another segment of the credits. Whether all these odd responsibilities mean she's more trusted than the other intern or a bigger target is a matter of speculation.
The old guy in glasses from Ned's Newt. Began as a pet store owner, then continued to pop up in various roles. He even pops up at the beginning of one episode ("Summer Gone, Summer Not") to point this out.
Spaced Out has Guy, who turns up in pretty much every job on the space station besides its custodian, school teacher and supply shuttle pilot. His official job description is being the station's "Everything" (it's occasionally implied that he is actually a robot). Especially curious, considering that the station is the size of a large town and has fully stocked amenities (all run by Guy) despite their being a total of eight other residents.
The recurring red mustache guy from Courage the Cowardly Dog holds many different jobs depending on the episode. Many of his jobs include working as a Nowhere police officer, an archaeologist, a captain, a pilot, a New York police officer, a ranger, a general, a pirate, and a mayor.
Yosemite Sam of Looney Tunes fame. Starting out as a Western outlaw, he has since been a pirate, a prison guard, a Hessian, a claimjumper, a Medieval knight, a sheik, a politician, a Roman centurion, a Confederate officer, and many more.
Miss Rabbit in Peppa Pig - doing every random job is a running joke.
Mr. Ford on Frisky Dingo. He's been a mental hospital worker, a pet store clerk, gun store clerk, security for underground rabbit fights, polling consultant for Killface's presidential campaign, political analyst for a news show, US Secretary of State, and US President.
DoorMouse from Team Umizoomi. He can go from guarding doors to guarding bridges to even capturing sharks. So far he's doing a good job at it.
Crunchy from Dan Vs. Most of the time, he changes jobs because Dan makes him lose his in one way or another.
Even though she's usually a singer, Betty Boop is often shown working at different jobs in her cartoons.
Avatar: The Last Airbender has an episode where we meet a guy under the identities of Dock the ferryman, Xu the shopkeeper, and Bushi the river cleaner. Word of God has it that he has a split personality because his mind is screwed up from the pollution in the river where he gets his water.
A running gag in George And Martha was a certain creepy lizard guy always showing up as an employee of whatever franchise the titular hippos were frequenting. Usually right behind George.
Laurence "Larry" Needlemeyer from The Amazing World of Gumball has this, seen working in almost every video/video game store, a gas station, a grocery store, and a pizza place.
Treeflower, Norb's Love Interest from The Angry Beavers always seems to have a new job, and new personality aspects to match. This is lampshaded in the episode where Norb and Dag try to tease her and end up being teased right back by the tribe of female raccoons from an earlier episode.
On Peg + Cat, Ramone seems to regularly change from one job to another.
Lampshaded in one of Dane Cook's routines about "The Scary Guy at Work":
"Even now at your job, there is a freak. There is a weird guy at every job... And the strange thing about it is, it's the same guy, at every single job you go to. He's there, you quit, you go to the new job, and you're like "Oh my God, isn't that the guy from the other job?! 'It's the guy! THE SCARY GUY!'"
Vladimir Putin has alternated between being President and Prime Minister of Russia in order to abide by the constitution (which limits presidents to two terms served consecutively, but not total).
Winston Churchill. Besides being a soldier, journalist, novelist, painter, and historian, within the British government he was Prime Minister, Chancellor of the Exchequer, Home Secretary, First Lord of the Admiralty, Undersecretary of State, President of the Board of Trade, Minister of Munitions, Secretary of State for War, Secretary of State for Air, Secretary of State for the Colonies, Minister of Defense, Conservative Member of Parliament, and Liberal Member of Parliament. This doesn't include all the obscure honorary positions he accumulated, like Lord Warden of the Cinque Ports or Chancellor of the Duchy of Lancaster. He was also a licensed bricklayer.
Many high schools tend to do this by hiring an extra teacher whose specific job is to cover other teachers who're off sick, regardless of what the teacher's actually trained to teach.
This actually was tried in the commune New Harmony, Indiana started by Robert Owen. He insisted doing this too, and became a baker... unfortunately everyone agreed that his bread was inedible. A sign that his idea wasn't that great, and subsequently, the commune faltered.
In NASCAR, from 2010 to 2013, Kurt Busch has gone through four teams and four different car numbers: the #2 Miller Lite Dodge at Penske Racing in 2010, the #22 Shell/Pennzoil Dodge at Penske Racing in 2011, the #51 Chevrolet at Phoenix Racing in 2012, and the #78 Denver Mattress/Furniture Row Chevrolet at Furniture Row Racing in 2013.