10 Celebs Who Mastered the Pivot — and Their Net Worth 

Estimated Net Worth: $820 million

Dr. Dre (real name: Andre Romelle Young) began his career as a rapper, known for his trailblazing work with N.W.A. and his groundbreaking 1992 debut album The Chronic. He soon branched out into other areas, finding further fame as a producer, music mogul (heading up Death Row Records) and audio engineer. It’s that latter sideline that brought him to the biggest deal of his life, when he utilized the skills he honed in the studio to create his own line of headphones, Beats. When Apple bought Beats in 2014 for a reported $3 billion, Dre’s cut (reportedly in excess of $600 million) gave him what Forbes described as “the biggest single-year payday of any musician in history.”

Estimated Net Worth: $500 million

Few actors epitomize the phrase “movie star” better than George Clooney, who’s also branched out into directing and producing. And while he wasn’t exactly cash-strapped as one of Hollywood’s hottest stars, entering into the tequila business with pal Rande Gerber (husband of supermodel Cindy Crawford) is what really brought in the big bucks. In 2017, Clooney and Gerber sold their Casamigos tequila brand for an estimated $1 billion — with a “b” — netting each a cool half-bil. We’ll drink to that.

Estimated Net Worth: $490 million

Ellen DeGeneres’ success as a standup comic led her to television, where she starred in the hit sitcom Ellen until its cancellation in 1998, a year after she came out as openly gay. She returned to TV in 2001 with another sitcom, The Ellen Show, which bit the dust after just 13 episodes. In 2003, she took a left turn and entered the notoriously competitive daytime talk show genre, where dozens of bigger stars than her saw their shows crash and burn. For DeGeneres, however, daytime proved to be a natural fit — and viewers took notice. Not only did the show quickly became the hottest show on daytime, it’s maintained that status for more than a decade, catapulting her net worth into the stratosphere.

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Estimated Net Worth: $400 million

The Barbados-born singer who topped the charts with such hits as “Umbrella” and “Diamonds” refocused her efforts in in 2017 by taking the leap into the world of fashion and cosmetics. Her Fenty Beauty line, launched in September of that year, brought in a staggering $570 million in revenue in 2018, while her Savage X Fenty line of lingerie, launched in 2018, is already valued at $150 million, and getting more popular by the day.

Estimated Net Worth: $400 million

Arnold Schwarzenegger is one of the rare celebrities who’s managed to successfully undertake several career pivots. The native Austrian first came to public attention as a champion bodybuilder, eventually entering the movies and quickly becoming Hollywood’s top big-screen action hero. At the height of his fame, Schwarzenegger took a hiatus from movies and ran for governor of California. Not only did he win the election, he wound up serving two terms, holding the office from 2003 to 2011. Since then, he’s returned to acting, recently resurrecting his most iconic character in the 2019’s Terminator: Dark Fate. YOU MAY ALSO LIKE: 20 celebrities who married billionaires.

Estimated Net Worth: $400 million

The Olsen twins had only been alive for a year when they were cast on Full House, sharing the role of Michelle Tanner. The sisters parlayed their sitcom fame into a full-fledged empire with their Dualstar Entertainment company, churning out direct-to-video movies, clothing and assorted merch and making themselves multimillionaires before hitting puberty. While the failure of their second big-screen effort, New York Minute sent the company into dormancy, the sisters re-emerged to launch their wildly successful fashion line, Elizabeth and James (and subsequent line The Row). As a result, the former sitcom kids are now widely respected — and ridiculously wealthy — fashion icons.

Estimated Net Worth: $370 million

Once upon a time, Kim Kardashian was viewed as a wannabe Paris Hilton, an over-privileged pseudo-celebrity who picked up a cheque every time she appeared at a nightclub. Everything changed in 2007 thanks to the leak of her notorious sex tape and the premiere of the Ryan Seacrest-produced Keeping Up with the Kardashians, rocketing her to fame and fortune as reality TV’s biggest star. Kardashian proved to be full of surprises when she also wound up being a savvy entrepreneur, raking in big bucks on social media, apps, and various business ventures that sent her net worth soaring. In 2019, she made an even more dramatic pivot when she revealed she was studying to become a lawyer, with plans to advocate for prison reform — who could have seen that coming?

Estimated Net Worth: $320 million

Given that his father and various wrestlers all made a living as professional wrestlers, it was kind of a no brainer that Dwayne Johnson would enter the family business. When he was eventually signed to the WWE, he quickly became the league’s biggest draw shrewdly managed to parlay his WWE fame into some movie roles, which grew bigger and bigger — as did his paycheques — to the point that that he’s now the biggest box-office draw in the world. Combined, Johnson’s movies have grossed more than $10 billion worldwide.

Estimated Net Worth: $40 million

Blind since the age of 12, Andrea Bocelli graduated from law school and spent a year as a court-appointed attorney in his native Italy. While attending law school, Bocelli would pick up spending cash by performing in piano bars. In 1992, a tape of Bocelli singing “Miserere” wound up in the hands of opera legend Luciano Pavarotti, which led to performing at competitions and eventually being signed by a major record label. While his debut album was certified gold in the Netherlands, it was his second LP, 1995’s Bocelli that really put him on the map, while his 1999 release, Sacred Arias, became his best-selling release, selling five million copies to become the highest-selling classical music album in music history.

Estimated Net Worth: $14 million

A native of Detroit, Ken Jeong graduated from medical school and while also maintaining an interest in improve comedy. While practicing medicine in New Orleans, he competed in a 1995 comedy competition and won. As it happened, NBC president Brandon Tartikoff and Bud Friedman (owner of iconic LA comedy club The Improv) were judges; so impressed by his performance, they encouraged Jeong to move to LA — which he did, performing in comedy clubs by night while working as a doctor by day. Slowly but surely, the started landing roles, which paid off in 2009 with his breakout performance in comedy mega-hit The Hangover and being cast as obnoxious Ben Chang in NBC sitcom Community that same year. These days, the former physician (he no longer practices) can be seen as one of the judges on Fox’s bonkers singing competition The Masked Singer, one of TV’s hottest shows.