A senior business figure who, regardless of their many duties and responsibilities to their company, is presented as ruled by their vices and only interested in self-gratification.
Expect the Executive to regularly blow insane amounts of money on pointless extravagances and self-indulgence, be it through sex, food, alcohol, drugs (cocaine is particularly popular from The '80s onwards), gambling or just strange and bizarre activities.
Typically used as a satire of the (at least perceived) mechanics of hyper-capitalism and consumerism, they embody and often amalgamate some of the worst stereotypes of the industry. In more light-hearted settings, expect them to be presented as well-meaning and just enjoying spending their wealth in unusual and possibly extreme manners, while darker variations will often depict their activities as depraved, unpleasant and often flat-out illegal.
Don't expect their hedonism to ever have a negative effect on their standing within the business world, or interfering with their ability to do their jobs (not that they're likely to be seen actually working) as basic logic would tell you it should. Even if they're drunk and high 24 hours a day and blow this year's gross profit on hookers, they'll not only keep their jobs, but are likely to get recommended for a promotion.
It's equally rare for them to make any effort to hide their vices (except maybe from their superiors, though they are likely to turn out to be just as sleazy and hedonistic if not worse). Expect to see them happily engaging in Hookers and Blow right in front of everyone during office hours as a minimum.
Male executives are common for this depiction, but more recent works have seen female examples as well. Potentially this may be a sign of further, more extreme low morals, but this is not always the case. If they're also a member of The Syndicate, The Mafia or Those Wacky Nazis (and the like), in particular, they're expected to be competent in running the fronts even if they can be hedonistic and flaunt their riches everywhere.
While by definition required to be presented in a negative manner, don't expect this trope to be a complete summary of the executive's moral character or even their competence. It's entirely possible for them to reveal a hidden caring side, or potentially a surprisingly degree of functionality and ability.
Compare Sleazy Politician, another character which embodies negative stereotypes about their profession; Conspicuous Consumption, a similarly negative depiction of pointless and overly extravagant waste of wealth only one which focuses on physical possessions as opposed to actions and lifestyle; and Decadent Court, which is very much this trope's predecessor (only with a heavier focus on political intrigue than simple self indulgence). Contrast Rich Idiot With No Day Job, who only pretends to be this (and potentially doesn't even have any of responsibilities or a job); and Work Hard, Play Hard, when the characters wild behaviour is presented as in hand, or even complimenting, their high capability and work ethic at their jobs.
Note: The key point of trope is the "excess", many entrepreneurs have vices and enjoy a good time like any other human. If they are merely presented as enjoying their free time or only get up to reasonable antics, then they don't qualify.
- A Wendy's televised ad invokes this by having the Chief of a burger chain aboard his yacht, martini in one hand, cigar in the other, flanked by bikini bunnies. Then he gets a phone call from Clara Peller: "Where's the beef?" The cigar snaps, the martini spills and the corpulent chief tips over in his chair. Not a good day.
- The Ultimates: Deconstructed by Tony Stark. He goes from a Work Hard, Play Hard highly functioning businessman to spending most of his time partying, drinking and sleeping with various women. However, he's discovered that he has an inoperable and terminal brain tumor, and the debauchery is his way of distracting himself from dealing with that fact.
- Dilbert: The CEO enjoys a haywire lavish lifestyle. The Sunday 15 March 2015 installment has Dilbert give reasons for a pay raise, while Dogbert lists the Chief's excesses: "Solid gold toilets," "Every elevator has a full kitchen," "The entire house rotates for maximum sun exposure." Another strip has this man advise guests to approach his private helipad from the north, so as not to frighten the dwarf pawns on his human chessboard.
- The Apartment: All the company managers receive this treatment, with them all happily exploiting the opportunity to use Bud Baxter's Upper West Side apartment to carry out their extramarital affairs with multiple different women. But in particular the personal director Jeff D. Sheldrake stands out. A sleazy serial philander Sheldrake has cheated on his wife with literally dozens of women, many of whom were his own employee's (including his long suffering secretary Miss Olsen), stringing them along by pretending to be planning to leave his wife for them. He spends the film constantly pursuing his latest victim Fran Kubelik.
- Boiler Room: Subverted. The "businessmen" at J.T. Marlin are all professional con artists involved in a pump and dump scheme, and have made ridiculous amounts of cash, but don't really know how to spend it. When they get together after work at Greg's house, it's entirely empty except for a tanning bed and a flatscreen TV.
- The Devil's Advocate: John Milton, head of the highly prestigious law firm of Milton, Chadwick and Waters, somehow finds the time to drop everything and take Kevin Lomax on a search for a chicken who can play tic-tac-toe, attend a party in which he takes part in none of the networking enacted by the other guests, and drag Kevin along on a tour of New York's nightlife featuring a boxing match, a night out at a fancy restaurant, and another party in which Milton is seen receiving a blowjob...all this when they're supposed to be getting ready for a trial. Of course, this turns out to be fully justified given what Milton really is: not only does he not actually need to sleep, but he's fully capable of being in multiple places at once, being witnessed working, corrupting Kevin, and raping Kevin's wife at the same time across the city.
- Die Hard: Harry Ellis is Holly's smug, sleazy co-worker at the Nakatomi Plaza. He's introduced making unwanted advances towards Holly at the Christmas party and is seen snorting cocaine at least twice.
- Horrible Bosses: Once Bobby Pellitt takes over the role of running his deceased father's company, not only does he run it into the ground through incredibly bad decisions and firing employees willy-nilly, he spends all of his time locked in his office having orgies or getting stoned.
- Iron Man: Tony Stark starts off as this. While he owns Stark Industries, and does do a good deal of work on the design and technical side of a number of their cutting edge projects (as well as being personally involved in a few of their most important deals), he leaves the actual running of the company to Obadiah Stane, preferring to spend his time partying, drinking and having one night stands with random women, to the point he skips out on a award ceremony in his honour to spend the night at a casino and has his private plane include paid dancers. He grows out of it following his experiences. Deconstructed in that it was him acting this way that allowed Stane to manipulate him and misuse the company to sell arms to terrorists. Stark is naturally horrified to discover the sheer amount of corruption and death his negligence has let occur. He briefly relapses into his former bad habits (even taking them to outright self destructive levels) in Iron Man 2, it's a consequence of knowing that he's slowly dying and being unable to find a cure to the metal poisoning from the tech that's allowing him to be Iron Man and keeping him alive.
- Requiem for a Dream: In a montage at the end, Marion is shown to have become a prostitute for her drug dealer, who pimps her out to well-paying executives. The entire scene is treated as degrading and unnerving by "Psycho" Strings.
- Wild Things 2: Niles Dunlap is a CEO who turns out to have been a degenerate gambler and womanizer, to the point where he started mis-allocating company funds to sustain his addiction. He faked his own death with his stepdaughter's help so he could avoid any prosecution, unaware that she was actually using him as part of her own plot.
- The Wolf of Wall Street: Jordan Belfort, already the head of a corrupt stock-brokerage firm operating a pump-and-dump scheme on hundreds of duped investors, is notoriously hedonistic: in his own words, he gambles like a degenerate, drinks like a fish, fucks hookers five or six times a week, and does so many drugs over the course of his day he practically timetables them. Plus, he hosts ludicrously decadent parties for his employees at the end of every month, and took his fellow brokers on a stag night that wrecked the entire 28th floor of the Mirage hotel, which had to be refurbished out of Belfort's own pocket. A lot of the stuff we see in the movie actually happened, with a few exceptions (they never brought a chimpanzee into the office, for instance, nor did they ever do a dwarf-tossing contest).
- American Psycho: Patrick Bateman has a very high-paying job with his company (vice-president in the film adaptation) but he's never seen doing any real work. As such, most of his time is spent wasting time in his office, eating at ludicrously fashionable restaurants, dancing in clubs, hoovering up cocaine, and screwing prostitutes...then murdering them in cold blood. Then again, Patrick's father owns the company...
- Dave Barry in Cyberspace: A sample form letter from a corporate H.R. officer to a group of employees being laid off begins by ruefully listing various adverse economic factors for the company and its line of business "combined with the fact that OUR C.E.O. needs a jet with a bigger hot tub."
- The Magicians: Justified. Towards the end of the story, Quentin Coldwater decides to leave magic behind and get a job in the real world via the Brakebills' old boys network. As a result, he ends up in the position of associate management consultant at Gunnings Hunsucker Swann, and thanks to the enchantments placed on the job, he can waste as much time as he likes without repercussions. Most of his time is spent gaming, jacking off to internet porn, or getting shitfaced, to the point that his assistant has given up on trying to schedule him into meetings. Ludicrously enough, Quentin is actually able to delude himself into believing that he's become a happy, responsible adult member of society by doing this... until his old friends convince him to stop running away and become a magician again.
- Red Dwarf Infinity Welcomes Careful Drivers: Justified. Rimmer ends up becoming one of these when he returns to Earth, using the publicity to kickstart the creation of a business empire. However, despite his world-famous business acumen Rimmer is never seen at work as CEO at any point, instead usually hosting lavish parties atop his Paris HQ, going on drunken joyrides across history in the company time machine, and playing strategy games with Julius Caesar, George Patton and Napoléon Bonaparte. It turns out that the crew never returned to Earth at all, and they're actually trapped in a game of Better Than Life: in Rimmer's part of the game, his fantasy of being rich and successful has become a reality, allowing him all the benefits of being a wealthy CEO with none of the drawbacks.
- Underground: Leo James, the protagonist of this novel. As he notes, his modus operandi for seducing potential investors was to take them on progressively debauched tours of the local pubs, to the point that one particular night out in Canberra ended with him being thrown out of every single bar in the city. Also, once it becomes clear that Australia's new dystopian government isn't likely to see much in the way of tourism, he abandons the construction of his luxury resort and sets up shop in the only suite outfitted for display purposes, chugging scotch, snorting up cocaine by the truckload and screwing his assistant publicist—while a tropical cyclone is bearing down on the place. Finally subverted when, instead of accepting Prime Minister Bernard James' offer of a luxurious life as a collaborator, Leo turns him down out of sheer disgust and willingly accepts death by firing squad.
- Blackish: Dre's boss Leslie Stevens, co-founder and CEO of Stevens & Lido, is regularly suggested to be one. Whilst at work he's most often portrayed as lazy and clueless, regularly slacking off to discuss Andre's issues, he also casually implies that amongst other things he repeatedly cheats on his wife, has got at least one of his maid's pregnant and gambles with company money. Its also a recurring joke for him to slip into casual conversation a vague offhand reference to some extreme escapade or other he's done, such as mentioning that he once crashed a boat full of cocaine and prostitutes into California. Along with the long list of more seriously illegal acts he's potentially done (in particular the implication he regularly has to cover up for his son Connor actions), this is always Played for Laughs.
- Coroner: Vic Stenton the Victim of the Week of Bunny turns out to be one of these, a cannabis tycoon as well as indulging himself in his own product Vic had a taste for orgies, regularly holding them in his own luxurious apartment with the Toronto swinger community, prostitutes he hired and an employee he pressured into joining solely to make himself look better. Is ultimately the reason he died as his wife was outraged at him almost exposing his antics to their six year old daughter and stabbed him to death.
- How I Met Your Mother: Whilst his exact job is left unrevealed until late in the series, it's clear from the start that Barney Stinson is a senior figure in Goliath National Bank. Likewise, the man has pretty much dedicated his life to seducing and sleeping with as many women as is humanly possible, boasting to have slept with over two hundred at one point and regularly creating massively complex schemes to convince his latest target to sleep with him (afterwards he rarely sees them again). He's also revealed to be a compulsive (although highly skilled) gambler.
- Mad Men: All the Sterling-Cooper executives get up to a lot of debauchery over the course of the show, though most of them are Work Hard, Play Hard types who balance their hedonism with genuine productivity. The exception, and the truest example of this trope, can be found in Roger Sterling: because he was born wealthy and inherited his position, he doesn't treat the job seriously, and can often be relied upon to waste time or drink heavily at work. Also, it's not uncommon for him to be seen in the aftermath of orgies or experimenting with drugs. In one memorable instance, he actually had a heart attack during an attempt to carry on with his playboy lifestyle and nearly died.
- Jessica Jones (2015): Downplayed (at first) in the case of Jeri Hogarth; despite being the deathly-serious head of a law firm, she does seem to spend an inordinate amount of time screwing her secretary, eventually resulting in trouble when Jeri's wife finds out. In the second season, though, a sudden diagnosis of ALS and an attempted takeover of the firm results in her going off the deep end of hedonism and indulging heavily in drugs and prostitutes.
- Kids in the Hall: There was a sketch featuring a board meeting amongst several heads of different companies. When the meeting begins, an employee shouts "But first, the whores!" which causes scantily-clad women, mood lighting, and music to emerge. The CEO of the main company shouts that this is not how he runs his company.
We have the meeting first, and then the whores!
- 30 Rock has two downplayed examples:
- While not a major focus of his character, NBC Executive Jack Donahue is often seen drinking scotch during office hours (even once pouring himself the entire bottle), with several characters outright calling an alcoholic multiple times throughout the series. He likewise at one point happily relates the time he went hunting manatee (even keeping a framed picture of the manatee he shot on his office wall).
- Similarly, Jack's own boss and mentor Don Geiss. While always seeming wise and professional, it's established that even into his seventies he has several much younger mistresses, both of the male and the female variety, and his funeral reveals he has no less than two additional secret families (one Canadian, one attic).
- It's Always Sunny in Philadelphia: Already an abusive, greedy and transparently criminal businessman (to the point it seems the majority of his wealth came from embezzlement, tax fraud and multiple illegal ventures rather than actual work), Frank Reynolds is likewise a massive hedonist who regularly sleeps with prostitutes, openly does multiple drugs and flat out refuses to spend his vast fortune on anything other than enabling the Gang's insane and depraved schemes. It's best demonstrated in "Franks Back In Business" when he's temporarily called out of semi-retirement in the hope of saving his company, Frank instead blows money on outrageous purchases such as eating sushi off a naked prostitute rather than actually trying to save the company.
- Vampire: The Masquerade:
- The "Mystic Artist" character template started out like this. A wealthy businessman, he was originally a straightforward Work Hard, Play Hard type who liked to drink a little after work to relax. Then he started doing cocaine for an edge at work. Then, despite being married, he started hiring prostitutes to deal with more exotic sexual appetites. Eventually, indulgence became more important to him than work - or his wife and children, for that matter - and his pursuit of bigger thrills led him to the Followers of Set; they got him so addicted to vampire blood that he was willing to abase himself in troughs of human shit just for another taste of vitae. In the end, his excesses cost him his job, his money, his family and his self-respect, exactly as the Setites intended. Having been broken of his obsession with worldly pleasures and allowed to see the true nature of the universe, the character has been Embraced into the Followers of Set, and now works as an artist.
- The "Degenerate" character template of the Giovanni Clan. Though born into wealth and power, members of the Giovanni family have to distinguish themselves in the eyes of their elders if they want to be made vampires - most commonly in business. However, the Degenerate wanted to make a bigger spectacle of himself, and once he'd earned the proxy kiss and became a ghoul, he started indulging in progressively more grotesque acts of hedonism - mainly because he enjoyed the attention he gained as a result. By now, nobody in the family can remember the corporate feats that made him worthy of the Embrace; all they can remember are his acts of depravity, from injecting cocaine into his penis to getting his sister and his daughter pregnant. These days, the Degenerate spends his days in a whirl of parties and revels, kept afloat by the family money, unlikely to do anything worthwhile - corporate or otherwise. For this reason, he's regarded as a failure and an embarrassment.
- One of the most powerful vampires in Chicago is Horatio Ballard, a 19th-century robber baron notorious for his ludicrously expensive twelve-course meals, regular indulgence in gallons of booze, and morbid obesity. For good measure, his fortune was only secured through a mixture of extremely shady deals and the murder of his uncle; unfortunately for Ballard, his excesses eventually led him to two near-fatal heart attacks before he finally met with Prince Lodin of the Ventrue clan. Even now that he's a vampire and no longer needs to eat, Ballard still enjoys gorging himself on food and alcohol at every opportunity - especially if it means grossing out his fellow Ventrue. Of course, by this time, Ballard has the advantage of supernatural powers to guarantee his success in spite of his apparent indolence.
- Maria Kenyon, a minor character from one of the clanbook prologues. A hardworking, well-educated employee well on the way to the upper echelons of management, the long workdays and highly-competitive atmosphere forced her to seek out something that could give her an edge - namely cocaine. Unfortunately, Maria skipped the Work Hard, Play Hard phase and descended straight into flat-out excess when took her addiction home... and started using crystal meth. Her increasingly erratic behavior led to her being investigated and found out: Maria was fired to avoid a scandal and eventually reduced to being prostituted by her scummy drug dealer. Her story does end on a disturbingly happy note, as she ends up being "taken in" by the Followers of Set and reborn as a vampire - with the added bonus of keeping her ex-pimp as a slave.
- Promises, Promises: Being a musical adaption, J.D. Sheldrake follows the same beats as his film counterpart. A powerful personal manager at the insurance agency Chuck Baxter works at, Sheldrake is also a serial philander, who regularly cheats on his wife with multiple women and is eager to exploit Baxter's apartment to do so with his latest target Fran Kubelik. However, as opposed to the originals depiction as a manipulative sleazy executive, this version of Sheldrake is portrayed as somewhat more sympathetic and complex, with him getting an entire song ("Wanting Things") devoted to him trying to understand why he is constantly drawn to affairs and can't be content with the family he has.
- The Secret World: Kirsten Geary serves as a comparatively positive example of this: a hard-working executive within the The Illuminati—who are managed and organized like a corporation—she nonetheless has a serious eye for vice. From time to time, she'll ask you to bring back some of the more hallucinogenic substances you stumble across, and every so often, she'll be unable to send you a text debriefing due to attending an office party with an open bar... and on one occasion she ends up sending the debriefing while completely hammered (as evidenced by the deteriorated spelling).
- The Onion: "'Layoffs Are Necessary If We Want To Keep The Lights On,' Says CEO Halfway Through Tasting Menu" has a CEO eating a $150 ten-course meal with a $110 bottle of wine on the company's dime, all while describing his plans to lay off about 30 employees to "reduce our overall cost structure." He intends to discuss the matter further at his country house.
- Archer: Features this whenever Malory Archer's personal life crops up. Despite being the head of the private intelligence agency ISIS, she takes the job only slightly more seriously than her dimwitted son, Sterling: she fakes terrorist attacks to gain personal attendance at restaurants and airships, wastes company money on ludicrous personal luxuries, drinks on the job almost as much as Sterling, and has actually been carrying on a series of sordid affairs with a number of VIPs around the world including the head of the KGB, which often extends to having phone sex with them in her office during work hours! In the end, these dodgy deeds and many more committed over the course of the show ends up getting ISIS shut down by the FBI.
- Batman Beyond: Paxon Powers, the estranged son of Derek Powers, inherited Derek's selfishness and lack of morals but not his malice, ambition or intelligence. Following exposing his father as the supervillain Blight and convincing the Wayne-Powers Board to make him the new CEO, Paxon turns his attention to pure self indulgence, proceeding to spend nearly all his time at private parties and in the company of attractive swimsuit-clad women, barely making any effort to run his new conglomerate. He later reveals he charges his entire lifestyle to "company subsidies" and pays for nothing himself.
- Bojack Horseman: Played With. Butterscotch Horseman, Bojack's bitter, arrogant, hyper conservative father is a variation. A former working class aspiring writer, he eventually accepted an unspecified but high up and high paying post at his father-in-law's company, the Sugarman Sugar Cube factory, purely to shut up his wife Beatirice. Utterly despising the position (and heavily implied to not be remotely qualified to hold it), Butterscotch only interest was working on his novel on the weekend. Thus he turned to alcoholism, adultery (its confirmed he had an affair with his secretary, another with his maid which resulted in him accidentally fathering a child when she was forty years his junior and its implied he also did so with multiple other women) and spending all Beatrice's inheritance to distract himself.
- King of the Hill: Buck Strickland, Hank's boss and owner of Strickland Propane, lives his life in utter debauchery. He regularly cheats on his wife with his much younger secretaries and hookers, takes part in illegal underground gambling matches, spends his company's money on horse races, drinks and eats to excess (to the point he's had so many heart attacks that several parts of his heart have had to be replaced to keep him alive) and at one point buys emus to hunt. According to Hank he used to be far more straight-laced, but at some point his wealth went to his head.