These Hollywood Celebrities Moonlight As Successful Businessmen and Entrepreneurs

IMAGE Casamigos / Aviation Gin

We know these gentlemen by name and face. They’re the among the bigshots of Hollywood: action stars, rappers, Oscar winners, and more. But aside from their stellar careers in show business, these celebrities also moonlight as successful businessmen, some with entire empires in their portfolio.

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Here are the very famous businessmen with successful runs in entrepreneurship:

1| Ryan Reynolds

It’s hard to imagine Deadpool around a boardroom table unless it’s to assassinate someone while cursing profusely. But when he’s not entertaining the masses on the big screen, Reynolds plays his hand in entrepreneurship like a boss. In 2018, he acquired a stake in Aviation American Gin before he sold it in 2020 to Diageo, the company that includes Smirnoff and Johnnie Walker in its lineup. Reynolds will earn up to $610 million in the sale, with $335 in the initial payment and up to $275 million in the payout based on sales over the next 10 years.


Aside from liquor, Reynolds also dabbles in tech as he also owns a stake in Mint Mobile, an affordable mobile service, and is on the board of Match Group, which operates the likes of Tinder.

2| George Clooney

When he’s not busy being the husband of Amal Clooney, a world-renowned human rights lawyer who’s defended prime ministers, journalists, and whistle-blowers from persecution, George has a reputation for making good business decisions like when he co-founded Casamigas Tequila in 2013 with Rande Gerber, husband of Cindy Crawford, and Michael Meldman.

In 2017, the trio sold the brand for a whopping $700 million, also to Diageo, with up to $300 million based on sales in the next 10 years.

3| Paul Newman

After cementing his legacy in the golden age of Hollywood, the late Paul Newman co-founded Newman’s Own food products, which includes the household salad dressing with Newman’s face on the front. The business has now expanded to include pasta sauce, frozen pizza, salsa, and more.

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But the best thing about Newman’s business is that he decided to put all the post-tax profits and royalties to charity, and so far, the donations have exceeded $500 million.

4| Dr. Dre

Before Beats, Dr. Dre was already a veteran of the hip-hop scene and had earned Grammys for his rap albums, eventually establishing himself as a producer of up-and-coming artists like Kendrick Lamar. Then Dr. Dre tried his hand at entrepreneurship with a brand of headphones called Beats, which quickly became a hit with youths and music lovers alike. In 2014, Apple made its biggest purchase at the time by acquiring Beats for $3 billion, making Dr. Dre one of the richest men in hip-hop.

5| Jay-Z

This chart-topping artist isn’t just making good investmentshe’s making culture in a way only Jay-Z would dare to do. The rapper started his entrepreneurial journey with a clothing line called Rocawear, which he sold in 2007 for $204 million, then went on to open 40/40 Clubs around the country, own and sell his stake in Barclays Center and the Brooklyn Nets, set up his own music streaming service Tidal, invest $200 million in Armand de Brignac, and launch his own cigar line.


But it was Roc Nation, his real brainchild, that defined Jay-Z’s business portfolio. An entertainment agency, Roc Nation currently has the following artists in its roster: Rihanna, Normani, Big Sean, The Dream, and Meek Mill. It also manages DJ Khaled, Megan Thee Stallion, and Mariah Carey. Roc Nation has also co-produced television series, including the dystopian show Noughts + Crosses on the BBC, and it also produced the Super Bowl LIV.

6| Robert De Niro

Like his character in The Godfather trilogy, De Niro has his own business empire, but this time it’s completely legal. We promise. De Niro was one of the three businessmen who invested in chef Nobuyuki Matsuhisa, the mastermind behind Nobu, which now has around 30 locations worldwide. The restaurant and hotel chain is now valued at an estimated $500 million.

He also owns Tribeca Grill in New York City and a number of hotels in New York and Barbuda. Nobu has a number of hotels around the world, which might be why the name is familiar as a Nobu Hotel is located in City of Dreams, Manila.

7| Magic Johnson

Magic Johnson is one of the leading examples of athlete investors. The basketball legend has a conglomerate called Magic Johnson Enterprises that’s valued at around $700 million. Johnson was instrumental in Starbucks’ venture into urban areas after he persuaded Starbucks CEO Howard Schultz about his vision. He then purchased 125 stores that proved to perform better than other stores in the chain.

8| P Diddy

One of the wealthiest celebrities in Hollywood, P Diddy (Sean Combs) was able to maintain and then grow his wealth through smart business decisions and ventures, like his Sean Combs clothing line, Bad Boy Entertainment record label, Revolt TV network, and a number of restaurants.

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Anri Ichimura
Section Editor, Esquire Philippines
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