One African-American gentleman from an Ancestry.com ad says that his great-grandfather was born a slave but died a businessman. Possibly not as rich as other examples at the end, but among the poorest of starting points.
Anime and Manga
In Binbou Shimai Monogatari, Asu and Kyou briefly move in with their rich aunt, but choose to return to their normal lifestyle shortly afterwards.
A major premise in Stepping On Roses (Hadashi de Bara wo Fume), in which the poor and uneducated protagonist Sumi Kitamura is offered the chance to live a life of wealth and extravagance... but only if she is willing to leave her family behind to enter into a marriage of convenience with Princely Young Man Soichirou Ashida.
Later we see that there's also a a Rags to Royalty deal... since Sumi turns out to be Aiko Iijuin, the long-lost daughter of another rich family.
Love Lucky: Fuuta goes from living in a small room paid for with his modest wages to Ippongi Hills, the most high class, glamorous set of apartments in Tokyo so that he and his new pop-star wife Kirari can have easier access to each other in her off time.
For that matter, Swiss himself. Liechtenstein mentions that his own economic situation was not the best when he took her in due to the war and the GD, but some decades later he's living in a Big Fancy House with her an is a quite more wealthy nation. (Not that he spends a lot, though.)
Also the Netherlands. He's seen as a rather poor and struggling teenaged nation (while his younger sister Belgium is a Child Prodigy businesswoman), then he's seen under Spain's wing (that he's not too happy about), and later he has become quite the overseas empire... and a stoic, penny-pinching Non-Idle Rich.
Rukia Kuchiki from Bleach. From a Street Urchin who barely managed to survive to teenagehood with her friend Renji, to the adoptive sister of the leader of the very noble and filthy rich Kuchiki clan.
Also used in Haou Airen, where a girl who has to struggle with a part-time job, her highschool studies and taking care of her Ill Girl widow mother and her cute little siblings... is suddenly thrown into a world of fabulous riches and luxury in Hong Kong, when it turns out that the handsome stranger whose life she saved is actually a highranked Triad leader who wants her as his mistress (and he also promises to send money to her family in Tokyo, so the girl's mom can have adequate treatment and she won't have to worry - and as far as we know, he keeps that part). Too bad this also brings HORRIBLE misfortuneto the poor girl, as the dude is a massive Bastard Boyfriendand the people in their surroundings are corrupted to the core.
Sheryl Nome from Macross Frontier was a homeless Street Urchinafter her parents were assassinated until she was picked up by Grace O'Connor, who became her manager on the road to stardom. Ten years of hard work (and Grace's manipulations) later, and Sheryl is the most popular (and probably the richest) Idol Singer in the galaxy with a credit rating high enough to hire an entire high tech mercenary unit complete with their carrier flagship and Super Prototype fighters for a high risk rescue mission with just her credit card.
Candace White aka Candy Candy is a Heartwarming Orphan brought into the Legan family to work as a maid and a companion to Spoiled Brat Eliza, but at some point she catches the eye of the Andrees (a very highclass clan that the Legans are a branch family from). She first befriends the three boys of the Andree clan (Anthony, Stear and Archie), and later she's adopted into the Andrees per the orders of one of the leaders, Great-Uncle William (Actually the identity of the fourth young man of the clan, Albert, the uncle of the three mentioned boys). However, Candy becomes the Rebellious Princess of the clan, refusing to bend over to the aristocrats and then deciding to become a nurse without their support.
A more straightforward case would be Annie, Candy's "adopted sister". She was adopted by the rich Brighton family several years before, and the Brightons keep this as a secret since they're afraid that the already pathologically shy and insecure Annie will be ostracized and bullied. (This turns out to be true, unfortunately). It takes Annie several years to fully develop into a stronger, more self-assured person.
Yukiji from Kamisama Kiss used to be a ordinary farm girl before being adopted into nobility. The heroine Nanami also counts, though with her it is more of a case of Rags to Godhood.
In Sakura Gari, Dr. Katsuragi is implied to come from a low-middle class family since as a teenager he lived and worked as a servant in the very rich Saiki clan's Big Fancy House while going through his studies. Now he both works in a famous hospital and is the personal doctor of his former protectors.
Souma Saiki, too. His Missing Mom was an Impoverished Patrician and his Princess in Rags maternal grandma made him work in the streets. Then he was found by the Saikis clan and, since he was the most qualified to be the prospect heir (Youya was much younger and from an unhappy marriage), they took him in.
You Houki from Fushigi Yuugi comes from a very poor country family, and she is taken by the Royal Court due to her incredible beauty. She is then made into a membress of Hotohori's harem, and she eventually becomes his legal wife, the mother of his child, and the Empress Dowager.
In the short story in My Little Pony Micro Series Issue #3 Hayseed Turnip Truck grinds himself up until he becomes a successful businessstallion.
Parodied in FoxTrot, when Jason wins $10.00 - combined with his previous savings, he becomes a millionarein Turkish Lira - 77,000 to the dollar. Sadly, his opulent lifestyle comes crashing down when he loses his entire fortune buying five comic books.
Subject of a gag in one Don Martin cartoon for MAD: a scruffy-looking panhandler hits up a man in a business suit. The suit-wearer snaps "Get a job!" as he stalks past. Cut to the panhandler, still sporting the same ratty outfit and hairdo, sitting behind a large desk in an office high up in a skyscraper.
Forrest Gump: In addition to shaping mid to late 1900's pop culture and history, Forrest along with Lieutenant Dan become rich seemingly overnight in the shrimping business following hurricane Carmen destroying every boat but theirs. As Forrest puts it:
Forrest: Shrimping became real easy after that
In another example, Forrest donates most of the shrimping money to Bubba's family. His mother faints from merely seeing all that money.
Pretty Woman Vivian goes from heart-of-gold prostitute to a life of luxury with Edward, her sugar daddy and white knight.
Cinderella Man showcased the Real Life rags-to-riches story of boxer Jim Braddock. Happened against the backdrop of The Great Depression, making it all the more heartening that the man climbed out of absolute poverty on mostly guts and perseverance.
Barry Lyndon: Redmond Barry, irish commonner, ends up a rich English nobleman married to beautiful woman. Then subverted : Barry dies "poor and childless" as prophesised by the narration.
Envy: Nick Vanderpark (Jack Black) made himself a wealthy man by financing the development of a spray that vaporizes dog poop (hence the name "Vapoorize"). Tim Dingman (Ben Stiller), Nick's friend, best friend and former co-worker also becomes wealthy when Nick offer him partnership in exchange of Tim helping Vapoorize to be marketed in Italy. It seemed they'd no longer be wealthy when Vapoorize was recalled from the market but then Tim thought about inventing Pocket Flan. How much they made from the idea is never revealed.
Trading Places: Both Billy Ray Valentine and Ophelia leave their rather humble Philadelphia roots to become absurdly wealthy by the film's end. The butler Coleman ends up being able to afford a butler. The most notable case is Winthorpe, who begins the movie rich, then is driven to homelessness and nearly suicide, and ends the movie having bankrupted the people responsible for his temporary destitution and it is implied he's far more wealthy than he was at the movie's beginning.
The Rocky movies, also about a poor Philadelphian finding success and the attendant riches. Particularly noticeable in the second and third movies.
Lonesome Rhodes of A Face In The Crowd, went from a drifter with only one spare shirt and a guitar to his name to having the top two floors of a New York Hotel.
Malazan Book of the Fallen contains a highly ironic instance of this trope. After working to collapse Lether's economy while living in a hovel, Tehol Beddict accidentally becomes the new Letherii Emperor.
The 'rags' part was actually self-imposed. Tehol Beddict came from a very prominent family and was at one point one of the richest men in the country due to his business genius. He gave up his fortune because he was disgusted with the debt-slavery system the country run on. At any point in time he could have easily regained his previous wealth and power if he chose to.
In Horatio Alger's first book, Ragged Dick, Dick is able to elevate himself from homeless bootblack to...entry-level Clerk. While the "riches" part may seem a bit underwhelming, there's no doubt he's better off at the end than the beginning.
Virtually every Horatio Alger, Jr. story ever written follows this same plot. Poor boy works hard, is virtuous, and is helped by a kindly older man (keep this in mind for later), and he eventually makes his fortune, relatively. The "helped by a kindly older man" part of the trope is often forgotten, and for good reason - the real Horatio Alger, the writer? Was a ephebophile. Sadly, this is not scurrilous rumour but established historical fact.
Ragged Dick itself was followed up by a sequel book that went more in depth on the "to riches" part.
In Neuromancer, the protagonist undergoes this, going from a broke former console jockey to living the high life while on a mission.
In Count Zero, Marly Krushkova is raised to wealth to perform a task by the incredibly wealthy recluse Joseph Virek.
"A Song of Ice and Fire" demonstrates this in a similar vein to "The Great Gatsby" with Petyr 'Littlefinger' Baelish, who was born into the poorest noble family in Westeros, but thanks to his financial talents and a severe Break the Cutie process in his childhood that inspired him to get back at the nobility, he is now possibly the richest man in Westeros besides the Lannisters.
And Bronn who by his own badassery alone goes from sellsword to lord.
The Frey family made their fortunes through business yet the other Great Houses see them as wannabe upstarts.
Sweet Valley High book #16: "Rags To Riches". Roger Barrett was living with his poor, sick, single mother in a shabby house. She dies and it's revealed that he is actually Bruce Patman's cousin. He moves into the Patman mansion and changes his name to Roger Barrett Patman for the remainder of the original series. he dies in the earthquake
In Citizen of the Galaxy: The main character, Thorby, goes from literal rags (as a beggar and slave) at the start of the book to infamous riches (when he's returned to his wealthy dead parents' estate) at the end. The wealth ends up being a burden as much as a wish fulfillment: although he still gets to fight slavers, he does so in the most effective way via decisions and investigations behind a desk rather than in the most cathartic way via action and excitement on a ship.
Lori starts Aunt Dimity's Death working as a temp and having lived in a succession of cheap apartments after her divorce. Most of her things are in boxes, and she sleeps on a mattress on the floor. She describes her feelings on seeing the Boston office of Dimity's American attorneys for the first time: "Great, I thought, Willis & Willis Meets the Little Match Girl." After coming into her inheritance, she at first displays a certain reluctance to spend money, but eventually is found consigning her old wardrobe to Oxfam in favour of items like silk-lined custom trousers, handmade Italian boots, and a sumptuous black cashmere swing coat. "I'd never been a clotheshorse, but I was learning fast."
Harry Potter: goes from wearing his cousin's ill fitting hand-me-downs, to learning that he has a vault full of gold that he has inherited from his well-off parents, and then he inherits Sirius Black's estate. We never really find out just how much he inherited from either, but the Potters and Blacks were both old, well heeled, Wizarding families.
Pular Singe, from the Garrett, P.I. series, goes from browbeaten indentured servitude to a gang boss among TunFaire's lowest-of-the-low minority (ratpeople), to a junior partner in Garrett's investigations and up-and-coming investor in Amalgamated. Not rich by human standards, but an unprecedented success story by those of her own kind. And she's still young.
Samuel Vimes of Discworld stumbled his way into this, and has managed to constantly stumble his way into more wealth, titles, and fame since the whole thing with the dragon. And he's somewhat reluctant about the whole thing.
Inverted on Arrested Development. Actually, it's the whole premise of the series - a wealthy Southern California family loses their money and many members have to deal with actually working for the first time. Hilarity Ensues.
The premise of the new series Windfall; twenty people share a lottery jackpot, to the tune of about 17 million each. It's played for drama.
In British comedy/drama series At Home With the Braithwaites, the mother of the family wins 37 million pounds on the lottery... and doesn't tell her family for weeks. Naturally, wacky hijinks ensue.
In Farscape, the crew of Moya starts off as a penniless band of escaped prisoners. They even come close to starving. However, after robbing the alien equivalent of Fort Knox they're more or less flush with cash for the rest of the series. It doesn't hurt that half the time the traders they come in contact with don't survive to collect their fees.
Ryan from The O.C. is a poor kid who is taken in by the very wealthy Cohen family. Sandy Cohen has this as his back story, as he was poor before he married Kirsten.
In Smallville it is revealed that Lionel Luthor's parents were drunken, abusive, and poor. He himself is one of the riches men on the planet thanks to a large of number of not quite legal dealings.
CSI NY Sid Hammerback the coroner is pretty much a working class guy, managing okay but by no means wealthy-until his new pillow design is sold to a Japanese group for over 20mil.
Part of mankind's Back Story in Star Trek. A couple of centuries before the series begins, humanity has warred itself to near extinction following a third World War, complete with a wrecked Earth and barely any resources. Then a scientist builds the first prototype starship and attracts the attention of the Vulcans, and in the space of barely a century, disease, hunger, and poverty are eradicated. The turnaround is so drastic that the idea of "needing money" is a vague and distant memory. This complete 180 is a major defining plot point in human history, it's Rags to Riches on a planetary scale.
In The Legend of Zelda: The Wind Waker, there's a town called Windfall Island which contains a rich man and a poor man, both of whose daughters have been kidnapped by the Big Bad. You rescue the daughters about halfway through the game, and their fathers switch wealth (the rich man spends his fortune trying to rescue his daughter, while the poor man makes his fortune selling rare necklaces his daughter brings home).
Every Harvest Moon game begins this way. The standard is to give you a couple of farming tools and a single bag of seeds. By end game, most players would probably have obtained a ranch, upgraded their home to a fairly comfortable living space and make thousands of bucks a month off crop harvests and animal produce.
A specific character in which this is Inverted for is Lumina, if you marry her. She goes from living in a mansion and being one of the richest people in town, to living on a measly farm. She's more than happy with it too.
Pretty much every Final Fantasy game does this. At the beginning, you may have a few hundred Gil which can buy a Potion or two and perhaps slightly improved armor. By the end, you have hundreds of thousands of Gil and a full inventory of healing potions and equipment.
In Elite Beat Agents, you cheer on a pirate who has been left with practically nothing but his trusty bird, and he struggles to find lots and lots of treasures. If you succeed, the bird drops the trope title. In another mission, you cheer on an ex-oil tycoon who gets thrown out by his gold-digging wife after his oil wells run dry, and is determined to dig his way back back to riches.
The plot of pretty much every Grand Theft Auto game involves a small-time criminal going to the top. The worst example is definitely San Andreas, where CJ starts off as a gangbanger in a small ghetto with nothing but the clothes on his back and a bicycle, and within less than a year (In game time. In real time, people have completed the game in a day or less.) becomes a millionaire, manager to one of the greatest rappers in the world, owner of various properties, including an airfield and a share in a casino, and literally controls the entire state of San Andreas.
Rockstar has stated that they were tired of the implausibility of these plots, hence their decision to not rehash them in Grand Theft Auto IV.
They did have Franklin in Grand Theft Auto V who pretty much goes from Rags to Riches like CJ as well, but that game had multiple protagonists and they (along with various other characters) were all Deconstructions of how GTA protagonists were portrayed.
The 1993 computer game "Rags to Riches - The Financial Market Simulation" from Interplay lets you make a fortune on the stock market with the money your parents have given you.
This is literally a name of one of the scenarios in Sim City 3000, where you have to fix up a Crapsack Madrid.
Louise from Fire Emblem: Rekka No Ken was a peasant girl that didn't have much aside of her archery skills, her kind heart and her incredible beauty. However, after she told a local rich bachelor (Lord Pent) that she'd protect him with her bow and arrows, he chose her as his wife over many more graceful and prettier girls. Now they're very Happily Married.
And earlier, we have Deirdre from Fire Emblem Seisen No Keifu. She was a young girl living in seclusion and feeling that she was trapped in her forest village, then fell in love and married a local lord, and after her heritage as the long lost child of an imperial prince is discovered, she becomes an Empress. Too bad she had to be mind-wiped first and then have her first husband horribly killed by the second, though.
The cutscenes in Rock Band 3 give off this vibe (something that wasn't present before, by the way): your band starts off playing for enough money to share a single pizza, and along the way they become festival headliners, make a tour to Japan, and then one day they get sick of all the fame and Loony Fans harassing them, and so they vanish from the scene in a fake plane crash.
In Dragon Age II, the main quest line of Act I centers around Hawke, a refugee in the slums of Kirkwall, attempting to gather enough resources to become a partner in a Deep Roads treasure hunting expedition, which eventually brings in enough money to bring his family back into high society. It can go even further, in the endgame, where a pro-Templar Hawke is appointed Kirkwall's new Viscount.
Real estate agent H. G. Higwig from Mad TV. He starts off as pretty much a bearded hobo. If you keep giving him profit by buying and selling studios, he'll get richer and richer until he's a smug businessman.
In Third World Farmer, once you work out the strategy, it becomes fairly simple to start getting ahead and even becoming rich. There is some debate as to whether this is intentional or not.
Phase of the Whateley Universe pulls a Riches to Rags to Riches move, getting kicked out of a fabulously wealthy family for having the gall to turn into a mutant. By the middle of the first novel, he's living in a basement room with almost nothing to his name, and having to eat his sister-in-law's 'cooking'. By the end of the eighth novel, he's a billionaire (again).
In that particular example, much is made of the fact that he's got next to no poverty-level survival skills, having been trained nearly from birth to be a megabusinessman. It's only after his parents are forced to cough up three hundred million dollars in the first story that he's able to apply his elite financial skills and connections to reclimbing the billionaires' ladder. It's lampshaded by other students at Whateley on his first arrival that while he may have lost his family and 98% of his inheritance, he's still wealthier than almost all of the rest of the campus put together.
One episode of Kim Possible sees Ron pick up a cheque for $99 million dollars of fast food royalties as a Continuity Nod. It doesn't last.
In the Futurama episode "Fish Full of Dollars" Fry becomes extremely wealthy after discovering that his old bank account is still active and has been accruing interest for 1000 years. The status quo is restored after Fry spends it all on anchovies.
The Main cast also briefly became millionaires in the episode Future Stock. They return to rags, of course.
In the Rugrats episode "Chuckie is Rich," Chuckie's dad wins the lottery and they briefly become very wealthy. Of course, thanks to the poor investment choices of Corrupt Corporate Executive Drew, who handles the money, the status quo is restored in the end.
In Doug, Roger was originally ridiculously poor, to the point he had to live in a trailer. However, in the Disney reboot, his family struck big on a real estate deal, causing him to rival Bebe in terms of how rich he is.
The Top Cat movie, "Top Cat and the Beverly Hills Cats" is precisely this to Benny.
Spook: It's the old rags to riches story.
Top Cat: Right, except Benny could never afford the rags.
Family Guy has the family win the lottery and Peter alienates his friends with his newfound snobby attitude because of it. Not only that, but the family foolishly spend their money on trivial things until they go broke. The Griffins then get rich again through the lottery, only to go broke again a week later. Quagmire helps the Griffins out with the profits he made in his investment and the family manages to get back to where they were before the lottery.
Penny Arcade, arguably the most successful webcomic around, has allowed for creators Mike Krahulik and Jerry Holkins to live the good life for several years now.
Oprah Winfrey is probably as much of a living example of this trope as physically possible.
A fair amount of billionaires were born in middle-class or even poor families. In fact, it is estimated that over 80% of American millionaires are first-generation rich.
Due to the phenomenal success of Harry Potter, J. K. Rowling went from living on state benefits to being one of the richest women in the world.
In a similar vein, Tyler Perry, at one point, lived in his car. His plays/movies about Sassy Black Woman Mable "Madea" Simmons enabled him to move from the car... to a multi-million dollar mansion in Atlanta.
Older examples: King Xerxes of Persia and Roman Emperor Diocletian worked their ways up their kingdom/empires's militaries and ultimately became rulers.
It wasn't that uncommon in Rome, actually. If you were a really good member of the military and Genre Savvy enough to keep yourself away of the dangers in such an environment (injury, backstabbing, etc.), you could work your way up constantly and enact the trope. More than one Emperor aside of Diocletian arrived to power this way. (Now, whether they stayed there... that was something else)
Toyotomi Hideyoshi. He's born as a sandal-bearer named 'Tokichiro Kinoshita'. Then he joins Oda Nobunaga, work his ass up to the point that he became Nobunaga's right hand man, avenges his death and finished what Nobunaga couldn't accomplish: actually unifying Japan and becoming the most powerful man in the nation.
Although the immediate downfall of his clan immediately after his death can partly be contributed of his status; he couldn't even forge a Minamoto/Taira lineage as everyone knows his background, which makes his family ineligible for the top posts in the country. He ruled as kampaku— not a shogun— because he was adopted by a Fujihara just before the fact, and his legitimacy was only sustained through his own power. (On the other hand, Tokugawa Ieyasu has been able to forge himself a Minamoto lineage and make himself eligible for shogun.)
Young Dave Thomas was born to a poor, single woman, who gave him up for adoption. His adoptive mother passed away when he was six and his father was then left to move around (with Dave in tow) while he sought work. Thomas began working at the age of 12 (to help support the family), dropped out of high school, served in the U.S. Army during the Korean War, learned how to cook, came back home, worked at a diner, married the daughter of the diner's owner, and got his big break by meeting Colonel Sanders and setting up a few Kentucky Fried Chickens to own and operate. When Thomas sold his KFCs, which became very successful because of his hard work, he earned enough money to settle down, but invested it instead in his own fast food chain, and named it after his ginger-haired daughter: "Wendy's". (And he did go back to get his G.E.D.)
Shania Twain had to help support her family when she was a teenager, after growing up very poor. She had to live out of her car when trying to break into the music business.
Sarah Jessica Parker was born into poverty in Ohio, but was able to become a well known actress as a teenager (Square Pegs) and a wealthy star through Sex and the City. She's even kept her family relatively close, as she bought her mother a house in New Jersey.
Basically anyone listed here. This list includes the best example of a "rags to riches" president in American history, Bill Clinton, who was able to go from being a poor kid raised by a single mother (who would later marry and provide Clinton with a stepfather and his younger stepbrother Roger) to becoming a Rhodes Scholar and a succesful lawyer, eventually becoming Arkansas governor and then president.
Second best. In terms of coming from absolutely nothing, Andrew Johnson has him beat. (Johnson's wife actually had to teach him to read. As he went on to become a U.S. Senator, the house of Congress even more elite at the time than it is now, he obviously was a good study.) Oddly enough, they also share the distinction of being the only presidents to be impeached.
Independent Minnesota author Amanda Hocking.
Justin Bieber. He went from a poor kid with a single mother in low-income housing to one of the most well-known celebrities of today.
The example from The Blind Side up in the Movie section really happened; Michael Oher is a real person, and one of the top offensive lineman in the NFL.
Ghenghis Khan was raised by a single mother (his father was murdered), his family was outcast and left to die in the steppes. He ended up conquering China and having all its riches.
Alexander the Great didn't have too good a start with being enslaved along with his father Philip of Macedonia to their enemies. In the end he conquered what was then the known world and had the riches of Persia at his feet.