In today’s world, fame alone no longer guarantees financial longevity. Many stars have built side hustles that now outperform their on-screen careers—a smart pivot that shields them from showbiz’s volatility and creates lasting wealth. Exploring these stories shows how the right business move can rewrite a celebrity’s legacy. From makeup empires to restaurants, these ventures aren’t just passion projects—they’re powerhouse money-makers. Here’s a look at seven celebrities whose side hustles blew up.
1. Selena Gomez: Rare Beauty Reigns Supreme
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Selena Gomez made her name acting on Disney and later with music, but her beauty brand, Rare Beauty, has skyrocketed in value. As of 2023, Rare Beauty generated $350 million in revenue—a staggering figure that likely dwarfs her earnings from showbiz gigs. With a sustainable approach and a strong social media presence, her side hustle has become a defining part of her legacy. For Gomez, Rare Beauty isn’t just a business—it’s a movement that’s helped her amass a net worth of $1.3 billion. Her beauty line shows how a side hustle rooted in authenticity can truly steal the show.
2. Drew Barrymore: More Than Just a Movie Star
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Drew Barrymore built her reputation in Hollywood, but her business ventures—Flower Films, cosmetics, wine, homeware, and a clothing line—have created a thriving entrepreneurial empire. Her Flower Beauty line sells widely at Walmart, and her lifestyle brand, Dear Drew, and Amazon fashion collaboration keep growing. Add in bestselling books and her talk show, and Barrymore’s side hustles now form the backbone of her public persona and income. This range of ventures sets her up as more than an actress—she’s a lifestyle mogul.
3. George Clooney: Casamigos Builds a Legacy
Image Source: YouTube/The Graham Norton Show
Although our sources are older, George Clooney’s tequila brand, Casamigos, remains a textbook example of a side hustle outshining an acting career. He co-founded the brand, and its eventual sale for a reported $1 billion cemented its dominance over his film earnings. It shows how shifting from scripts to spirits can result in legendary returns. Clooney’s success remains a benchmark for celebrity-founded businesses that truly break the mold.
4. Jessica Simpson: A Billion-Dollar Brand
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Jessica Simpson transitioned from pop stardom to the fashion world—and did it in a big way. Her Jessica Simpson Collection, featuring shoes and handbags, is poised to hit $1 billion in annual sales. She’s also branched into beauty and fragrances, cementing the talent behind the brand as far outweighing her early entertainment success. Simpson’s business acumen shows how side hustles rooted in personal style can challenge—and surpass—the fame that started them.
5. Emma Grede: Behind the Billion-Dollar Brands
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Though not a celebrity in traditional entertainment, Emma Grede’s work with SKIMS, Good American, and Safely has made her a business star in her own right. As co-founder and CEO of these brands, she’s heavily integrated celebrity backing—especially from the Kardashians—and controls significant equity: 8% in SKIMS, 23% in Good American, and 22% in Safely. Together, these ventures have propelled her net worth above $300 million, making her side hustle empire more notable than her media presence.
6. Jimmy Buffett: The Parrothead Empire
Image Source: YouTube/The Tonight Show Starring Jimmy Fallon
Legendary singer Jimmy Buffett is known for beachy tunes, but his Parrothead empire—from restaurants and hotels to branded merchandise and beverages—has become a massive retail and hospitality venture. Buffett’s side hustle dives far beyond the stage, crafting a lifestyle brand that earns more steadily—and perhaps reliably—than concert tours alone. His empire proves that building a brand around your persona can outlast the hits.
7. Scott Disick: Real Estate Over Reality Fame
Image Source: YouTube/Keeping Up With The Kardashians
Scott Disick rose to fame on reality TV, but his real estate and fashion brand “Talentless” has taken on a larger role in shaping his wealth and image. His show Flip It Like Disick follows his development projects—with flipping luxury homes becoming both a side hustle and the center of his public identity. His ventures now define him more than his time on Keeping Up with the Kardashians, showing how diversification can redefine celebrity.
Why Side Hustles Are Becoming Main Acts
From beauty lines to real estate, these success stories show one thing clearly: a strategic side hustle can surpass a primary career—especially in earnings, influence, and longevity. For celebrities, it’s not just about following passion—it’s about building security and ownership. Want to emulate them in your own way? Start a venture that aligns with your brand, empowers you creatively, and connects with a community. If done right, your side hustle could outshine anything you’ve already done.
Which celebrity side hustle has inspired you most—and what personal passion could you turn into your own thriving venture? Share your ideas or favorite examples in the comments!
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Amanda Blankenship is the Chief Editor for District Media. She frequently writes for a handful of blogs and loves to share her own personal finance story with others. When she isn’t typing away at her desk, she enjoys spending time with her daughter, son, husband, and dog. During her free time, you’re likely to find her with her nose in a book, hiking, or playing RPG video games.
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