Britney Spears once sang, “Boy, don't try to front I know just what you are. You got me goin'. You're oh so charmin.' But I can do it. Womanizer.” In other words, a womanizer is a guy that moves from woman to woman in a really short amount of time and usually doesn’t really take the woman’s feelings into consideration. Many male celebrities live life like this because they can have just about any woman they want. For the most part, celebrity womanizers aren’t celebrated but can become notoriously famous for it. At the same time, some celebrities are really good at keeping their image clean while still chasing after every woman they see. Some just can’t keep their eyes from darting from one woman’s assets to another’s.
Often fans and the media can become obsessed with a celebrity’s lifestyle and their relationships. When a celebrity couple breaks up it's covered by every media outlet, trends on Twitter and fans often pick sides. However, celebrity womanizers go through so many women and so fast that it’s impossible to keep up. They break hearts everywhere they go and generally don’t care about the consequences. Some celebrities spend their entire lives trying to build a career while other celebrities build a career out of breaking hearts. Here is a look at 15 of the Most Notorious Celebrity Womanizers.
15 Josh Hartnett
Some men are womanizers forever while some appear to have the ability to change. Josh Hartnett might fit into the category of someone who is willing to change. However, when he was single he was known for being a womanizer. Josh Hartnett has appeared in several films, such as Pearl Harbor, Black Hawk Down, The Black Dahila, Sin City and Lucky Number Slevin. He’s had a pretty decent career but that pales in comparison to the women he’s dated. He dated the prettiest actresses, hottest models and the most beautiful musicians. He’s also dated some of the sexiest and most famous celebrities in the world. He’s dated or been linked to Scarlett Johansson, Katie Holms, Penelope Cruz, Gisele Bundchen and Rihanna. However, even a womanizer like Josh Hartnett can be swept off his feet. Josh Hartnett has been dating Tamsin Egerton since 2013 and they had their first child together in 2015.
14 Jude Law
Jude Law is an Academy Award nominated actor who has achieved critical acclaim and commercial success. However, he might be best known for his love of women. Jude Law has appeared in several films, such as The Talented Mr. Ripley, Cold Mountain, Alfie, Hugo and The Grand Budapest Hotel. He’s also portrayed Dr. Watson in the Sherlock film series. Jude was married to actress Sadie Frost from 1997 to 2003 and has three kids with her. A year after their divorce he became engaged to Sienna Miller. In 2005, he issued a public apology to Miller after he cheated on her with his children’s nanny. They broke up in 2006 and he briefly dated model Samantha Burke who gave birth to his daughter in 2009. Also in 2009, Law and Miller briefly rekindled their relationship before splitting again in 2011. At one point he was dating Catherine Harding but they broke up and she later gave birth to his fifth child.
13 Gerard Butler
It seems that Gerard Butler can have any woman he wants and he takes full advantage of that fact. He first big opportunities came with his role in the miniseries Attila and in the film Phantom of The Opera. He went on to appear in several films, such as Tomorrow Never Dies, Reign of Fire and Lara Croft Tomb Raider: The Cradle of Life. He had his big breakthrough with his role as King Leonidas in the film 300. He’s been nominated for several awards, including Teen Choice awards, Saturn awards and MTV Movie Awards. He’s also known for being a bit of a womanizer and has dated a who’s who of the most beautiful women in Hollywood. He’s dated or been linked to Jennifer Aniston, Rosario Dawson, Shanna Moakler, Paris Hilton, Naomi Campbell, Lindsay Lohan and Cameron Diaz. There is a good chance that list will continue to grow.
12 Colin Farrell
Colin Farrell has appeared in several films, such as Minority Report, Phone Booth and Miami Vice. He also starred in the second season of HBO’s True Detective. He married singer and actress Amelia Warner on a beach in Tahiti. However in 2011, Warner said about the ceremony, "We had a ceremony on a beach in Tahiti that was by no means legal and we knew it wasn't... It was just a thing we did on holiday. We went shark feeding and then we did that. We booked them both on the activities desk at the hotel.” In 2003, he had a child with Kim Bordenave. Later, he dated writer Emma Forrest for about a year and Forrest published a memoir, Your Voice In My Head, about their relationship and the death of her therapist. The memoir is being adapted into a film. In 2009, he had his second child with Polish actress Alicja Bachleda-Curus and that relationship ended in 2010. He’s been linked to several of the most famous and beautiful women in the world, including, Britney Spears, Lindsay Lohan, Demi Moore, Paris Hilton and Angelina Jolie. He also sued his former ex-girlfriend and Playboy model Nicole Narin when she tried to release a sex tape they made together in 2003.
11 Gene Simmons
Gene Simmons is the co-founder, bass guitarist and co-lead singer of the iconic band, Kiss. His stage persona is known as The Demon. Kiss is known for painting their faces and elaborate stage performances. They have released several albums, including Kiss, Psycho Circus and Monster. The band is also known for their aggressive merchandising style, which is spearheaded by Gene Simmons. Besides being a rock icon, Simmons is also known for his love of women and his womanizing ways. Simmons has dated Playboy Playmate Shannon Tweed for roughly 28 years before getting married in 2011. He was initially against the idea of marriage but eventually gave into the concept. Most womanizers are against the idea of marriage until they either meet “the one” or are no longer on this earth. At one point he was in a relationship with Diana Ross and Cher. He apparently lived with both of them at separate points. He has bragged that he’s slept with over 4,600 women, including celebrities and fans.
10 John Cusack
It might be a bit of a surprise to some to know that John Cusack is one of Hollywood’s most notorious womanizers, unless you’re one of the women that have gone on a date with him. John Cusack first rose to fame with his roles in Better Off Dead and Say Anything. He went on to appear in several films, such as High Fidelity, Being John Malkovich and Hot Tub Time Machine. Cusack is known for his womanizing ways among celebrities. He’s dated a long list of women, inducing Jodi Lyn O’Keefe, Minnie Driver, Claire Forlani, Neve Campbell and Jennifer Love Hewitt. Jennifer Love Hewitt is credited with informing everyone with Cusack's dating style. As one story goes, he showed up for a first date with an unnamed actress and at the door asked if they just could have sex right away because he had to wake up early the next morning.
9 Wilmer Valderrama
Wilmer Valderrama is best known for his role as Fez in the hit Fox comedy, That '70s Show, from 1998 to 2003. He’s also appeared in several other TV series, such as From Dusk Till Dawn: The Series, Greys Anatomy, NCIS and The Ranch. He also hosted the MTV show Yo Momma and appeared in the film, Party Monster. He’s also expanded into a music career and released the song, “The Way I Fiesta”, as his alter ego Eduardo Fresco. He’s also known for being a womanizer and the long list of women he’s been with. From 2000 to 2002 he dated Mandy Moore. In 2004, he began to date Lindsay Lohan. He’s also been linked to Ashlee Simpson and Jennifer Love Hewitt. During an interview with Howard Stern, he rated how well Ashlee Simpson and Jennifer Love Hewitt performed in bed.
8 Warren Beatty
I bet Warren Beatty thinks this article is about him. Oh, wait it is, at least this part. Warren Beatty is an actor, writer and director. He has appeared in several films, such as Heaven Can’t Wait, Splendor in the Grass, Bonnie and Clyde, Shampoo, Dick Tracy, Bugsy, Bulworth and Rules Don’t Apply. He’s been nominated for several Academy Awards and won the Academy’s highest honor, the Irving G. Thalberg Award. His personal life and relationships have often been the center of attention. He’s been married to actress Annette Bening since 1992 but before that had a plethora of women to brag about. He had several relationships with well-known celebrities, including Julie Christie, Diane Keaton and Madonna. A biography about Warren Beatty claims that he’s been with 12,775 women. Musician Carly Simon confirmed in 2015 that the second verse in the hit song, “You’re So Vain”, is about Warren Beatty.
7 George Clooney
George Clooney is known for his critically acclaimed performances, his outstanding directing and getting with more women than movies he’s made. He first rose to fame with his critically acclaimed role on the TV series ER. He’s starred in several memorable films, such as Out of Sight, Three Kings and Up In The Air. Additionally, he’s directed the film Confessions of a Dangerous Mind, Good Night, and Good Luck and The Ideas of March. He won an Academy Award for his role in the film Syriana. He’s well known for his smoldering good looks that attract the hottest women in the world. He was married to actress Tailia Balsam from 1989 to 1993 and vowed to he’d never get married again. He went on to date several beautiful women, including Kelly Preston, Ginger Lynn Allen, Lisa Snowdon, Renee Zellweger, Krista Allen, Elisabeth Canalis and Stacy Keibler. Despite claiming he’s never going to get married again, he married human rights lawyer Amal Alamuddin in 2014. It seems that the world’s greatest womanizer is now retired.
6 Tiger Woods
Tiger Woods is widely regarded as one of the greatest golfers of all time. Additionally, he’s widely regarded as one of the most infamous womanizers of all time. Tiger Woods was ranked as the number one golfer in the world from 1999 to 2004 and again from 2005 to 2010. He’s won the PGA Player of the Year 11 times, won 79 PGA tours and achieved the Grand Slam three times. However, he’s well known for his womanizing ways despite his ability to keep it hidden for so long. He was married to former model Elin Nordegren until it was revealed that he had affairs with thirteen different women. His career took a huge hit and he lost several endorsements, such as AT&T, General Motors and Gatorade. He released a statement saying, "I thought I could get away with whatever I wanted to. I felt that I had worked hard my entire life and deserved to enjoy all the temptations around me. I felt I was entitled. Thanks to money and fame, I didn't have to go far to find them. I was wrong. I was foolish." After the divorce was finalized, he dated Alpine Skier Lindsey Vonn but they broke up in 2015.
5 Wilt Chamberlain
Wilt Chamberlain is a basketball legend and icon who held numerous records throughout his career. However, the record he is best known for is the claim that he slept with roughly 20,000 women. During his career he played for the Harlem Globetrotters, Philadelphia 76ers and the Los Angeles Lakers. He is two-time NBA champion and earned four MVP awards. He was notorious for his womanizing ways with Annette Tannander saying, “I think Wilt hit on everything that moved but never was bad or rude.” However, that has been disputed by David Shaw of the LA Times. He claims that he and his wife went to dinner with Wilt and a date. He noted that Wilt was being rude to his date and left to get the number of another woman.
Many of his friends claim that he once slept with 23 women in a 10-day period. If he was to have slept with 20,000 women that would mean he slept with 1.37 women per day from the age of 15 until his second autobiography, View from Above, was released. However, Chamberlin did say, "With all of you men out there who think that having a thousand different ladies is pretty cool, I have learned in my life, I've found out that having one woman a thousand different times is much more satisfying."
4 Hugh Hefner
Hugh Hefner was a womanizer before womanizing was even a thing. Hugh Hefner is the founder and C.E.O. of Playboy enterprise, which is best known for publishing Playboy magazine. His net worth is over $43 million. In 1949, he married Mildred Williams but she later cheated on him. Hefner noted that finding this out was, “the most devastating moment of my life.” She later allowed him to cheat on her in an attempt to salvage the marriage but it didn’t work. After, he reinvented himself as the millionaire playboy that he became famous for. He’s been in relationships with several playmates, including Carrie Leigh, Karen Christy, Sondra Theodore, Donna Michelle, Marilyn Cole and Shannon Tweed. In 1989, he married Playmate of the Year Kimberley Conrad who was 36 years his junior. They later divorced and he went back to his dating ways. He dated Holly Madison and the Shannon Twins at the same time. In 2012, he married playmate Crystal Harris when he was 86 and she was 26 years old.
3 John Mayer
John Mayer is great at two things; making music and being a womanizer. John Mayer has dated some of the hottest and most famous women in the world. He has released several critically and commercially acclaimed albums, such as Heavier Things, Room For Squares and Try. He has won two Grammy Awards for his work, one for the single, “Your Body Is a Wonderland” and the album Continuum. At one point he struggled with several personal issues and caused a huge amount of controversy with an interview he did for Playboy. The fallout from the interview led to him being labeled a racist, misogynist and kiss-and-tell boyfriend. He’s apologized for several of his harsh comments and regrets saying them. However, it’s safe to assume he doesn’t regret the long list of beautiful women he’s dated. John Mayer has dated or been linked to Jessica Simpson, Mandy Moore, Minka Kelly, Jennifer Love Hewitt, Katy Perry and Jennifer Aniston.
2 Jack Nicholson
Jack Nicholson is one of the most legendary actors of all time. He’s also one of the most legendary womanizers of all time. In fact, Maxim magazine even included him on their “10 Living Sex Legends”. Nicholson has appeared in several critically and commercially acclaimed films, such as Easy Rider, The Shining, Batman, Chinatown and The Departed. He’s won three Academy Awards for his roles in One Flew Over The Cuckoo’s Nest, Terms of Endearment and As Good As It Gets. He has several children with different women but was only married once to Sandra Knight. Actress Susan Anspach claims she had a son with him but Nicholson isn’t convinced the child is his. His longest relationship was with Angelica Huston but they were on again/off again for the most part and he had several relationships during that time. He’s dated and had affairs with Amber Smith, Lorraine Nicholson, Amanda de Cadenet, Michelle Phillips, Rebecca Broussard, Bebe Buell and Lara Flynn Boyle. It’s rumored that he’s slept with roughly 2,000 women.
1 Charlie Sheen
Charlie Sheen first rose to fame for several critically acclaimed performances in several films. However, he is best known for being one of the most notorious womanizers of all time. Charlie Sheen has appeared in numerous films, such as, Platoon, Wallstreet, Major League and Hot Shots. He also starred in several TV series, such as, Spin City, Two and a Half Men and Anger Management. At one time he was the highest paid actor on TV until he had a major falling out with the creator of Two and a Half Men, Chuck Lorre. He’s been married three times and has five children with different women. He’s been in relationships with several beautiful women, including, Kelly Preston, Brooke Mueller and Denise Richards. He’s also dated several adult film stars, such as, Ginger Lynn, Heather Hunter and Bree Olson. In 1995, it was revealed that he was a client of an escort agency run by Heidi Fleiss. It’s been rumored that Sheen has been with over 5,000 women. He was ranked second on Maxims 10 Living Sex Legends.