From Side Hustles to Billions: 10 of the Richest Women in Entertainment (mostly)

Money may not grow on trees, but these women have found a way to make it rain—on their terms. Whether through makeup, media, or music, they’ve turned their passions into billion-dollar empires. So, who are the richest self-made women in America? Let’s break it down, billionaire by billionaire, and get into the nitty-gritty of how they’re making their fortunes grow. Plus, I’ll add a few names to the list who are just as deserving of the spotlight.

1. Rihanna ($1.4 Billion)

Rihanna’s a global superstar, but it’s not just her music that’s bringing in the big bucks. RihRih has built a business empire that’s just as influential as her time on stage.

• Fenty Beauty: Launched in 2017 with an inclusive makeup line (40 foundation shades!). It brought in $550 million in revenue in its first year. Her partnership with LVMH solidified its global presence.
• Savage X Fenty: Disrupting the lingerie game with inclusivity, Rihanna's lingerie line is now valued at $1 billion. She owns 30% of the company.
• Fenty Skin: Expanding the Fenty empire, this skincare line focuses on products for all skin types and tones.

While we all wait for her next album, Rihanna is too busy stacking up cash from her beauty and fashion ventures. Who needs to tour when your businesses are on autopilot?

2. Oprah Winfrey ($2.5 Billion)

Oprah has built an empire on storytelling, but it’s her strategic investments that continue to fuel her billionaire status.

• Harpo Productions: Oprah’s production company has produced everything from her iconic talk show to The Color Purple on Broadway.
• OWN (Oprah Winfrey Network): Launched in 2011, the network continues to air content reflecting Oprah’s brand of positivity and personal growth.
• Weight Watchers: Oprah acquired a 10% stake in 2015, and her endorsement caused the stock to soar. She’s still a major shareholder today.
• Apple TV+ Partnership: Oprah’s partnership with Apple TV has expanded her media influence into the streaming world.

At this point, Oprah’s influence is like gravity—it’s everywhere, and we just live in it.

3. Kim Kardashian ($1.2 Billion)

Kim K turned her reality TV fame into a billion-dollar enterprise, and it’s not just from posting on Instagram.

• KKW Beauty: Kim launched this cosmetics line in 2017, which was a direct hit, bringing in hundreds of millions in its first year.
• Skims: Kim’s shapewear line is all about body positivity and inclusivity. The brand is valued at $4 billion, and she’s still the majority stakeholder.
• Mobile Apps & Fragrances: Before beauty and shapewear, Kim was making millions from her Kim Kardashian: Hollywood mobile game and a variety of fragrances.

Love her or hate her, Kim’s business decisions are as sharp as her contouring skills.

4. Kylie Jenner ($600 Million)

Kylie might not hold onto the "youngest self-made billionaire" title anymore, but she's still cashing in big time.

• Kylie Cosmetics: Launched in 2015 with lip kits, the brand exploded in popularity, earning her millions in revenue. She sold 51% to Coty in a $600 million deal, but she’s still the face of the brand.
• Kylie Skin: Capitalizing on her cosmetics success, Kylie expanded into skincare with products that have become cult favorites.
• Endorsements: Kylie’s Instagram following (over 370 million) brings in millions from sponsored posts and partnerships with brands like Puma and Adidas.

From lip kits to boardrooms, Kylie continues to cash in on her beauty empire.

5. Sara Blakely ($1 Billion)

The woman who revolutionized shapewear, Sara Blakely, started Spanx with $5,000 and a dream—and turned it into a billion-dollar empire.

• Spanx: Launched in 2000, Spanx revolutionized women’s shapewear with innovative products. In 2021, she sold a majority stake to Blackstone, valuing Spanx at $1.2 billion.
• Investments: Blakely invests in female entrepreneurs through her foundation and is part of Richard Branson’s space tourism venture, Virgin Galactic.
• MasterClass & Real Estate: Beyond Spanx, Blakely makes money through real estate investments and her popular MasterClass on entrepreneurship.

With Spanx now in the hands of Blackstone, Blakely’s fortune will only keep expanding—pun intended.

6. Shonda Rhimes ($250 Million)

Shonda Rhimes didn’t just dominate TV—she redefined it. If there’s a dramatic plot twist, it probably came from her mind.

• Shondaland Productions: Her production company is responsible for some of the biggest TV hits, including Grey’s Anatomy, Scandal, and Bridgerton.
• Netflix Deal: In 2017, Rhimes signed a $150 million deal with Netflix, ensuring that her future content will keep us glued to our screens for years to come.
• Books: Shonda’s best-selling memoir, Year of Yes, proved she’s just as powerful in print.

Her Netflix deal alone guarantees that she’ll continue to be one of the richest showrunners in history.

7. Beyoncé ($540 Million)

From music to business, Beyoncé is building an empire worthy of Queen Bey herself.

• Ivy Park: Beyoncé’s athleisure line, in collaboration with Adidas, has become a global success, thanks to her powerful personal brand.
• Tidal: Along with her husband, Jay-Z, Beyoncé is a co-owner of the streaming service, Tidal, which has turned into a solid revenue stream.
• Endorsements & Tours: From her Pepsi endorsement to her world tours, Beyoncé has no shortage of income streams outside of music.

With every move, Beyoncé makes sure her empire only grows stronger—and more flawless.

8. Madonna ($850 Million)

Madonna didn’t just break the rules—she rewrote them. The Queen of Pop has diversified her fortune over the years, proving she’s not just a music legend.

• Touring & Music Sales: Madonna’s tours are consistently among the highest-grossing in history, and her music catalog continues to sell.
• Maverick Records: She co-founded this record label, which managed artists like Alanis Morissette and Michelle Branch.
• Fashion & Fragrance Lines: Over the years, Madonna has launched multiple fashion lines and fragrances, adding to her empire.

Madonna’s ability to reinvent herself keeps her at the top, both creatively and financially.

9. Dolly Parton ($350 Million)

You know her for her songs, but Dolly’s wealth isn’t just from her music.

• Dollywood: Dolly’s theme park empire in Tennessee brings in millions of visitors each year, making it one of her biggest revenue streams.
• Songwriting Catalog: Dolly’s written over 3,000 songs, many of which are still earning royalties today. She even famously refused to sell "I Will Always Love You" to Elvis!
• Investments & Philanthropy: Dolly’s also invested in real estate and has given millions to charities, especially through her Imagination Library, which gives free books to children.

With Dolly, what you see is what you get—a business savvy woman with a heart of gold.

10. Reese Witherspoon ($440 Million)

From America’s sweetheart to business mogul, Reese Witherspoon has built an empire on female-driven storytelling.

• Hello Sunshine: Reese’s production company, which produced hits like Big Little Lies and The Morning Show, sold for nearly $900 million in 2021.
• Books & Fashion: With her book club and Southern-inspired fashion line Draper James, Reese has multiple income streams.
• Acting: Reese continues to act in and produce hit films and TV shows, keeping her in the spotlight and adding to her net worth.

Reese’s next role? Being the queen of entrepreneurial Hollywood.

Honorable Mentions: These Women Deserve to Be on the List

1. Jessica Alba - The Honest Company: Jessica's wellness brand focuses on clean, non-toxic baby products, and expanded into beauty and home products. Valued at over $1 billion, Jessica owns a significant share.
2. Huda Kattan - Huda Beauty: What started as a beauty blog quickly turned into a global cosmetics empire. With products sold in Sephora, Huda has become one of the most influential women in beauty.
3. Pat McGrath - Pat McGrath Labs: Known as the most influential makeup artist globally, Pat’s beauty brand is valued at over a billion dollars, with her products becoming iconic in the world of luxury makeup.