In 1976 Steve Jobs co-founded Apple in a Los Altos garage and, by the time the company went public in December 1980, he was worth roughly $250 million on paper at age 25. He had become the public face of the personal-computer revolution. Yet by September 1985 he had resigned from the company he created, after the board sided with CEO John Sculley and stripped him of any operational role.
The exile lasted twelve years. Jobs poured his money and reputation into NeXT, a high-end workstation maker that struggled to sell hardware, and into a small computer-graphics outfit he bought from Lucasfilm in 1986 and renamed Pixar. For most of a decade both ventures consumed cash. NeXT never became a commercial success on its own terms, and Pixar lost money year after year while Jobs covered the shortfalls personally.
The turn came in 1995, when Pixar released Toy Story, the first fully computer-animated feature film, and went public a week later in an offering that made Jobs a billionaire. A year later Apple, near collapse, bought NeXT for about $400 million, bringing Jobs back as an adviser. By September 1997 he was interim CEO of the company that had cast him out.
What followed was one of the most complete comebacks in business history. The iMac (1998), iPod (2001), iTunes Store (2003), and iPhone (2007) turned a near-bankrupt computer maker into the most valuable company in the world. Jobs sold Pixar to Disney in 2006 for about $7.4 billion, becoming Disney’s largest individual shareholder. He died in October 2011, having built two fortunes and reshaped several industries.
Robert Downey Jr. (born April 4, 1965) is an American actor whose career traced one of Hollywood’s most documented falls and recoveries. The son of underground filmmaker Robert Downey Sr., he emerged as a gifted young actor in the 1980s, briefly joined Saturday Night Live, drew strong reviews for Less Than Zero (1987), and earned an Academy Award nomination for Best Actor for playing the title role in Chaplin (1992).
From 1996 onward, drug addiction overtook his career through the public record of arrests and incarceration. He was arrested in 1996 on drug and weapons charges, served jail time in 1997 for missing court-ordered drug tests, and after a relapse was sentenced in 1999 to a term that included roughly a year at the California Substance Abuse Treatment Facility in Corcoran. Further arrests in late 2000 and April 2001 led to his dismissal from the television series Ally McBeal and left him, by industry accounts, effectively uninsurable.
Downey’s recovery is generally dated to his decision to get sober in 2003. That year, Mel Gibson personally backed the insurance bond that allowed him to star in The Singing Detective when studios would not take the risk. A well-received turn in Kiss Kiss Bang Bang (2005) reestablished his standing, and Iron Man (2008) made him the centerpiece of the Marvel Cinematic Universe.
The role of Tony Stark, reprised across a string of Marvel films, helped make Downey one of the highest-paid actors in Hollywood in the mid-2010s. In 2024 he won the Academy Award for Best Supporting Actor for Oppenheimer, completing a comeback from near career-ending addiction to the top of his profession.
Martha Stewart built one of the most recognizable lifestyle brands in American media, turning a basement catering business into a publishing, television, and merchandising empire. The 1999 initial public offering of Martha Stewart Living Omnimedia briefly made her, on paper, one of the first self-made female billionaires in the United States. Her name became shorthand for a particular ideal of domestic perfection.
That ascent stalled over a single stock trade. In December 2001 Stewart sold her shares in the biotech company ImClone Systems one day before the U.S. Food and Drug Administration publicly rejected a key ImClone drug. The sale itself drew scrutiny, but the case that ultimately brought her down was not about the trade. It was about what she told investigators afterward.
In March 2004 a federal jury convicted Stewart of conspiracy, obstruction of justice, and two counts of making false statements to federal investigators. She was never convicted of insider trading; the securities-fraud count tied to her stock was dismissed before the case reached the jury. She served five months at Federal Prison Camp Alderson in West Virginia, from October 2004 to March 2005, followed by home confinement.
The comeback was both commercial and cultural. Stewart returned to television, kept her company running, eventually sold the brand for hundreds of millions of dollars, and in her late seventies and eighties reinvented her public image entirely, partnering with Snoop Dogg and, at 81, becoming the oldest cover model in the history of the Sports Illustrated Swimsuit Issue.
George Foreman won Olympic gold in 1968 and the world heavyweight championship in 1973, demolishing Joe Frazier to take the title. He was a feared, brooding puncher until Muhammad Ali outlasted him in the 1974 Rumble in the Jungle, and a 1977 loss to Jimmy Young, followed by a religious experience, pushed him out of boxing entirely.
For about a decade Foreman was a preacher, not a fighter. During that time much of the money he had earned in the ring disappeared into failed investments and tax problems, leaving the former champion in financial difficulty as he approached middle age.
In 1987 Foreman returned to boxing, overweight and well into his late thirties, but with a transformed public image: genial, funny, and self-deprecating, the opposite of his menacing younger self. The comeback culminated on November 5, 1994, when, at age 45, he knocked out Michael Moorer to become the oldest heavyweight champion in history.
The larger fortune, however, came from a kitchen appliance. The George Foreman Grill, which carried his name and persona, sold in enormous numbers, and in 1999 the manufacturer Salton paid him a reported $137 million to buy out his name rights, on top of years of royalties, a payday that dwarfed everything he had earned in the ring.
Michael Milken reshaped American corporate finance from a single desk in Beverly Hills. As head of the high-yield bond department at Drexel Burnham Lambert, he turned the disreputable “junk” bond into a mainstream instrument, financing leveraged buyouts and capital-starved companies that the established banks would not touch. By the late 1980s he was the highest-paid financier in the country; Drexel paid him a reported $550 million in 1987 alone, and his influence over the credit markets was so concentrated that his annual Beverly Hills conference was nicknamed the “Predators’ Ball.”
That dominance collapsed under a federal securities investigation that began in 1986 and was advanced by the cooperation of arbitrageur Ivan Boesky. In March 1989 a grand jury returned a 98-count indictment charging racketeering, securities fraud and mail fraud. In April 1990 Milken pleaded guilty to six felony counts of securities and tax violations and agreed to pay $600 million in fines and penalties. He was sentenced to ten years in prison, served roughly 22 months after the sentence was reduced, and was barred for life from the securities industry.
Released in 1993 and diagnosed with advanced prostate cancer that same year, Milken rebuilt a very large fortune through private investing and ventures such as the education company Knowledge Universe, and he poured money and organizational energy into medical research. He founded the Prostate Cancer Foundation and built the Milken Institute into a prominent economic think tank, recasting himself as a philanthropist and convener.
In February 2020 President Donald Trump granted Milken a full pardon, citing his cancer-research philanthropy. His story remains contested: critics see a financier who broke the law and escaped lightly, while supporters point to a record of capital-market innovation and decades of disease-fighting giving. Notably, despite the popular “insider trading” label, the six counts he admitted concerned securities reporting, recordkeeping and tax matters, not insider trading.
By the end of the 1970s Francis Ford Coppola was arguably the most celebrated director in America. Within a single decade he had made “The Godfather” (1972), “The Conversation” (1974), “The Godfather Part II” (1974) and the punishing, triumphant “Apocalypse Now” (1979) — a run of artistry and Oscars matched by few filmmakers in history. Flush with success and ambition, he bought the old Hollywood General Studios and renamed it Zoetrope Studios, intending to build an artist-run alternative to the major studios.
He bet that vision, and much of his own money, on “One from the Heart” (1982), a stylized Las Vegas musical shot on elaborate soundstages. Against a budget reported at roughly $26-27 million, the film earned only a few hundred thousand dollars in its initial release. The loss was catastrophic. Zoetrope Studios collapsed, the studio property was lost to foreclosure, and Coppola was left carrying tens of millions of dollars in debt, filing for bankruptcy protection multiple times across the following decade.
The comeback came the hard way. For years Coppola worked largely as a director-for-hire, taking commercial assignments — “The Outsiders” (1983), “Peggy Sue Got Married” (1986), “The Godfather Part III” (1990) and the hit “Bram Stoker’s Dracula” (1992) — specifically to service his debts. In parallel he grew a Napa Valley wine business, built around the Niebaum-Coppola estate and the historic Inglenook brand, into a major enterprise.
That winery, not the film work, ultimately restored his fortune. Reportedly worth hundreds of millions of dollars, the wine business gave Coppola financial independence and, decades after “One from the Heart,” the means to self-finance his long-gestating epic “Megalopolis” (2024) by borrowing against his wine assets — a final, deliberate echo of the all-in gamble that had once ruined him.