The Top 10 Most Famous Sugar Babies of All Time


Last Updated: February 16, 2024

Sugar Baby

The sugaring lifestyle is becoming more mainstream all the time, and we have a few famous sugar babies to thank for it! These brave trend-setters have bucked the trend of traditional romance to create legacies that we can all admire. And it seems like they enjoyed quite a bit of glamor along the way.

Take a look at our list of the most famous sugar babies of all time:

Anna Nicole Smith

When it comes to the most widely recognized sugar babies, Anna Nicole Smith is the true G.O.A.T.

Born in Texas, the young beauty spent most of her early twenties supporting herself and her son with entry-level jobs. When she was 24 and working as an exotic dancer, she met a wealthy oil businessman, J. Howard Marshall, who was 86 at the time. Over the course of their 4-year relationship and marriage, Marshall showered his sugar baby with extravagant gifts and the encouragement she needed to pursue her modeling career. Before long, the ambitious young woman had catapulted herself into fame with a high-profile contract with Guess jeans.

Even though Anna Nicole Smith was one of the most well-known sugar babies of the era, legal fights with her late husband’s family made it difficult for her to enjoy any kind of financial benefit from her relationship. Although many didn’t understand her marriage, she always maintained that she loved her husband. And she certainly paved the way for future sugar babies.

The stars of the Playboy Mansion

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America’s most famous mansion is arguably the Playboy Mansion, which the late magazine mogul Hugh Hefner shared with his many sugar babies. Not only did the women who lived there enjoy the benefits of dating the founder of a multimillion-dollar business, but they also became reality stars. The Girls Next Door ran for 6 seasons, and some of the women would go on to star in spinoffs or other ventures.

While the Playboy Mansion is no longer, it went a long way in normalizing the sugaring lifestyle.

Hilaria Baldwin


Living in New York exposes you to all kinds of celebrities on a daily basis. But it’s not every day that a casual outing to a restaurant in Manhattan turns you into a celebrity, yourself.

Yet, that’s exactly what happened to Hilaria Baldwin (then Hillary Lynn Hayward-Thomas) when she happened to run into Alec Baldwin in 2011. Initially, her family was against the relationship because of the 26-year age gap between them. But, the couple followed their hearts and married the next year.

Hilaria’s relationship with the successful actor has allowed her to start new ventures in television, podcasting, and publishing. Today, she has a net worth of $10 million.

Kevin Federline

Whether you know him as Kevin Federline, or by his stage name K-Fed, one thing is for sure: at one point, everyone was talking about him. That’s what happens when you marry the most famous pop star of the early 2000s, Britney Spears.

The California-born backup dancer met Britney not on set, but rather at a Hollywood club. Even though he was already engaged and about to become a dad, Kevin left it behind in favor of a glamorous, paparazzi-filled lifestyle.

A reality television show of their life soon followed, as well as a surprise wedding in 2004. The couple had two kids together and then filed for divorce in 2006. But don’t feel too bad for K-Fed. The settlement awarded him over $1 million as well as ongoing child support.

Kimora Lee Simmons

If you don’t know the name Kimora Lee Simmons, chances are, you’ve heard of her clothing brand: Baby Phat.

Kimora’s rise to fame started when she was just 17 years old and working as a model in NYC’s Fashion Week. There, she met record exec, rapper, and business entrepreneur Russell Simmons, who was 18 years her senior. Despite earning some side-eyes, the pair married in 1998.

From there, Kimora made some excellent career choices, including starting her own spinoff of her husband’s clothing brand. She would also go on to appear in various television shows, including America’s Next Top Model as a judge.

Could she have done it on her own? Kimera certainly seems to be a savvy businesswoman. But, she definitely benefited from the support of her successful older husband.

Guy Ritchie

You might know him as a movie guy. After all, Guy Ritchie has made a name for himself as a director, screenwriter, and movie producer. But the thing that really added to Guy Ritchie’s status? His marriage to pop star, Madonna.

Guy was fairly early in his career when he was introduced to the singer in 1998. And although his joint ventures with Madonna weren’t necessarily successful, his relationship with her certainly added to his name recognition.

Their divorce has been called one of the most expensive settlements in history. Guy says it was never about the money, but no one doubts that the coupling propelled his fame, influence, and net worth.

Mariah Carey

There’s no doubt about it that Mariah Carey is a born star. Her vocal range has put her down in history as one of the best singers of all time. And she’s made money over the years with various fragrance lines, beauty products, and even a festive liqueur.

But her path towards celebrity status began with one very influential man: Tommy Mottola. The music exec first heard Mariah’s voice when she was just 17 years old, and immediately signed her to Columbia Records. The pair got married when she was 23 and he was 43.

Even though her relationship with Tommy offered Mariah an astoundingly successful start to her career, ultimately his jealousy and controlling nature soured the marriage. Maybe she learned a thing or two about how not to treat a sugar baby, because her next marriage to Nick Cannon (in which she was the older and more famous of the two) seemed to be a bit more blissful.

Coco Chanel

The name Coco Chanel conjures up images of elegant bottles of perfume and fashionable handbags. And as it turns out, the woman behind the brand is one of the most famous sugar babies in history.

Coco Chanel was born into adversity in France in 1883. She learned her sewing skills from the nuns who ran the orphanage where she grew up, and she spent her free time performing in clubs as a singer.

The ambitious young woman met her first sugar daddy at the age of 20, and never stopped seeking out new relationships that could advance her career and wealth. Before long, she had launched handbag, fashion, and perfume lines that would carve out her place in French high society. She never married, preferring to maintain her independence. But she was rarely seen without a rich or influential boyfriend.


Unless you have lived in or visited Los Angeles, CA during the last 40 years, you might not immediately know about the local legend, Angelyne. But you’ll love her story.

Shrouded in mystery, this blonde bombshell first came to prominence by appearing on billboards all over the “City of Angels” in 1984. Drivers were intrigued by the soon-to-be-iconic billboards which showcased Angelyne in a variety of poses and her name in bold lettering. She became instantly recognizable and famous, with locals and tourists keeping an eye out for her flashy pink Corvette. In many ways, Angelyne paved the way for future influencers and reality TV stars by being famous for nothing more than self-promotion. Indeed, she’s made quite a living for herself by being beautiful and elusive.

But, how exactly did she get her start? By striking up a relationship with a wealthy man named Hugo Maisnik. What were the terms of the arrangement? She got her face and name on a billboard and he enjoyed the boost in business that came with her overnight fame.

If you want to learn more about one of the least-understood famous sugar babies, you’re in luck. Emmy Rossum and Martin Freeman portray the business partners in a limited television series on Peacock.

Wendi Deng Murdoch

When Wendi Deng met the world-famous billionaire, Rupert Murdoch, she was an intern at one of his news businesses in China. She clearly made a great first impression because soon after, she resigned from her position and moved to New York City to marry her wealthy former boss.

But while Rupert may have introduced his new bride to the life of ultra-luxury in NYC, she also had a positive influence on his career. In fact, the 37-year age gap between them meant that Wendi was a useful bridge to some of the younger entrepreneurs like Mark Zuckerberg and Jack Dorsey.

The marriage ended after 14 years. And while it’s unclear how much she walked away with, she seems to have spent it wisely. Wendi has worked as an advisor for MySpace in China. And, she’s invested in Snapchat, Uber, and Warby Parker.

The most famous sugar babies are true inspirations!

As you can see, some of the most successful and influential stars of our time weren’t afraid to go after what they wanted. With a bit of ambition, luck, and willingness to buck traditional romance trends, they found partners who could help them make their dreams come true! They deserve their place on our list of famous sugar babies!

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