Sean “Puff Daddy” Combs and Cassie Ventura, 17-Year Age Difference

Sugar Daddy Sean Puff Daddy Combs and Cassie Ventura

With a net worth of about $580 mil­lion, Sean “Puff Daddy” Combs was the rich­est hip hop artist of 2013, beat­ing out icons like Jay-Z and Dr. Dre. Combs didn’t make his money just off rapping—he’s also a suc­cess­ful record pro­ducer, entre­pre­neur, and actor. In fact, most of his money comes from non-musical work. Sean “Puff Daddy” Combs started his career as the founder of Bad Boy Records in 1993, which went […]

Jason Statham and Rosie Huntington-Whiteley, 20-Year Age Difference

Jason Statham Sugar Daddy and Rosie Huntington

When you hear the name Jason Statham, the first things that come to mind are prob­a­bly guns, explo­sions, and a whole lot of butt kicking—all the mak­ings of an action hero. After a career of pro­fes­sional div­ing and mod­el­ing, Statham landed his first role in Guy Ritchie’s 1998 thriller Lock, Stock and Two Smok­ing Bar­rels. The shady con–artist char­ac­ter was a per­fect fit for the actor, who had pre­vi­ously worked as a […]

George Clooney and Stacy Keibler, 18-Year Age Difference

Sugar Daddy George Clooney and Stacy Keibler Relationship

From his days play­ing a young Dr. Ross on the tele­vi­sion series ER, George Clooney has grown to become a part of Hol­ly­wood roy­alty. Between his act­ing and direc­to­r­ial accom­plish­ments, Clooney has taken home over 60 awards, includ­ing two Acad­emy Awards, one BAFTA, three Golden Globes, and four Screen Actors Guild Awards. His per­sonal life has also been the sub­ject of end­less media hoopla, espe­cially since he made it very clear that […]

Ryan Phillippe and Alexis Knapp, 15-Year Age Difference

Sugar Daddy Ryan Phillippe and Alexis Knapp

Ryan Phillippe jump­started his act­ing career with a recur­ring appear­ance as Billy Dou­glas on the pop­u­lar soap opera One Life to Live—Billy was the first homo­sex­ual teen char­ac­ter on U.S. day­time tele­vi­sion. After spend­ing a year on the series, Phillippe migrated to L.A. He took on sev­eral roles in tele­vi­sion and film, includ­ing the teen thriller I Know What You Did Last Sum­mer, the risqué drama Cruel Inten­tions, and the Oscar-nominated mystery […]

Richard Gere and Cindy Crawford, 17-Year Age Difference

Sugar Daddy Richard Gere and Cindy Crawford

It isn’t uncom­mon to see movie stars and super­mod­els get­ting together—it’s like a moth to a flame. That’s why it wasn’t much sur­prise when actor Richard Gere started dat­ing super­model Cindy Craw­ford, despite their 17-year age dif­fer­ence. When the celebrity cou­ple first met in 1988, Gere was already a pop­u­lar actor with sev­eral hit films (like Oscar win­ner An Offi­cer and a Gen­tle­man), and Craw­ford had already estab­lished a suc­cess­ful mod­el­ing career. […]

Leonardo DiCaprio and Toni Garrn, 18-Year Age Difference

Sugar Daddy Leonardo DiCaprio and Toni Garrn

Born in 1974, Leonardo DiCaprio got his big break in show busi­ness at the age of 16, when he landed the recur­ring role of Luke Brower in the tele­vi­sion series Grow­ing Pains. Although he had done com­mer­cials and minor film and tele­vi­sion roles, join­ing the cast of Grow­ing Pains is what really set the stage for his suc­cess­ful career in act­ing. After Grow­ing Pains, DiCaprio moved on to film, receiv­ing crit­i­cal praise […]

Sean Penn and Charlize Theron,15-Year Age Difference

Sugar Daddy Sean Penn and Charlize Theron

Sean Penn, 53, is no stranger to high-profile romances. The 50-year-old Oscar-winner was once upon a time engaged to pop queen Madonna. The celebrity cou­ple tied the knot in 1985 and their mar­riage was wrought with vio­lence, mostly due to Penn’s wild tem­per. In 1986, he attacked musi­cian David Wolin­ski for hit­ting on his famous wife in a night­club, for which he was charged $1,000 and slammed with a year-long pro­ba­tion period. […]

Dennis Quaid and Kimberly Buffington, 17-Year Age Difference

Dennis Quaid and Kimberly Buffington Relationship

Den­nis Quaid has his brother to thank for a suc­cess­ful career in the spot­light. After watch­ing his brother win an Oscar, Quaid decided to drop out of uni­ver­sity and move to Hol­ly­wood to chase his own act­ing dreams. Although he strug­gled to get noticed, Quaid man­aged to land his first cred­ited movie role in 1977’s I Never Promised You a Rose Gar­den. Although he starred in a cou­ple other movies, it wasn’t […]

Johnny Depp and Amber Heard, 23-Year Age Difference

Johnny Depp and Amber Heard Age Difference

Johnny Depp has played a long list of mem­o­rable char­ac­ters on the big screen, like the title char­ac­ter in Edward Scis­sorhands and Don­nie Brasco, the enig­matic Cap­tain Jack Spar­row in the Pirates of the Caribbean series, the Mad Hat­ter in Alice in Won­der­land, and Tonto in the 2013 remake of The Lone Ranger. It isn’t too often that Depp plays the role of a roman­tic hero, but off the screen, he’s quite […]

Tracy Morgan and Megan Wollover, 18-Year Age Difference

Sugar Daddy Tracy Morgan and Megan Wollover

Tracy Mor­gan has earned his rep­u­ta­tion for being a fear­less come­dian both on and off the screen. Although he starred in a few films and tele­vi­sion episodes, includ­ing his own sit­com called The Tracy Mor­gan Show, he really hit the peak of celebrity sta­tus when he joined the cast of Sat­ur­day Night Live in 1996. He became even more famous after tak­ing on the role of Tracy Jor­dan in the pop­u­lar TV […]

David Cross and Amber Tamblyn, 21-Year Age Difference

David Cross and Amber Tamblyn Relationship

Fun­ny­man David Cross comes from hum­ble begin­nings. Grow­ing up, his fam­ily wasn’t very well off and after mov­ing around sev­eral times, they set­tled in Geor­gia, only to be evicted from their home a few years later. Cross began his career in com­edy doing stand-up per­for­mances through high school, later join­ing a sketch group at Boston’s Emer­son Col­lege. He became a reg­u­lar act at a club called Catch a Ris­ing Star, which is the […]

David Schwimmer and Zoe Buckman, 18-Year Age Difference

David Schwimmer and Zoe Buckman Relationship

You prob­a­bly know David Schwim­mer bet­ter as Dr. Ross Geller from the TV sit­com Friends. The actor landed the role at the start of the series in 1994 and held on to it till the final episode in 2004. Friends—which also starred Courteney Cox, Jen­nifer Anis­ton, Lisa Kudrow, Matt LeBlanc, and Matthew Perry—was a huge suc­cess, earn­ing 63 Emmy nom­i­na­tions among a slew of other awards. The rat­ings were a hit from […]

Russell Simmons and Hana Nitsche, 28-Year Age Difference

Sugar Daddy Russell Simmons And Hana Nitsche

Rus­sell Sim­mons is best known for co-founding the iconic hip hop label Def Jam Record­ings, which has signed super­star artists like Rihanna, Kanye West, Nas, and Frank Ocean. The label, which was even­tu­ally sold to Uni­ver­sal Music, made up only a frac­tion of Sim­mons’ com­pany, Rush Com­mu­ni­ca­tions Inc., which also man­ages artists, pro­duces films and tele­vi­sion shows, devel­ops a mag­a­zine, and runs an adver­tis­ing agency. On top of all that, Sim­mons has launched […]

Marc Anthony and Shannon de Lima,18-Year Age Difference

Marc Anthony and Shannon de Lima

Marc Anthony enjoyed a slow but suc­cess­ful rise to fame as a singer and song­writer in the Eng­lish music scene. He’s won two Gram­mys, among sev­eral other notable awards, and even landed a few film roles across big stars like Den­zel Wash­ing­ton, Al Pacino, and Sean Penn. Despite his own achieve­ments, Anthony’s fame really hit the roof in 2004 when he mar­ried his third wife, inter­na­tional super­star Jen­nifer Lopez. Hav­ing already fathered three […]

Princess Charlene, Prince Albert’s Much Younger Wife, Wants Kids of Her Own

Prince Albert and Younger Wife Princess Lynette Charlene

When a younger woman mar­ries an older man, one of the first ques­tions that comes up is whether or not they’ll have kids. It’s a hot topic because, while younger brides may be at the prime age for moth­er­hood, often their older hus­bands have either decided they don’t want kids, or have already done the dad thing—and have no inten­tions of doing it all over again. When Char­lene Lynette Witt­stock, 35, mar­ried 55-year-old […]

Bradley Cooper and Suki Waterhouse, 17-Year Age Difference

Bradley Cooper and Suki Waterhouse Age Difference

Bradley Cooper’s very first act­ing role was a single-episode appear­ance on the tele­vi­sion series Sex and the City in 1999. It was a small part, but it was the start­ing point of what would soon become an immensely suc­cess­ful act­ing career, and the begin­ning of his sta­tus as a bona fide celebrity. Cooper landed his first film role in 2001 play­ing a sum­mer camp coun­selor in the com­edy Wet Hot Amer­i­can Summer—it […]