19 Female Celebrities Who’ve Hooked Up With The Most Guys In Hollywood


A great many celebrities lead charmed lives. They can enjoy the finer things such as fast cars, expensive jewelry, and sprawling mansions. A lot of them have personal assistants and hangers-on that are at their beck and call. Of course, one of the perks that some of the biggest stars have is the ability to hook up with almost anyone at any time. Warren Beatty, Charlie Sheen, and Jack Nicholson are just a few of the many male stars that have been with more beautiful women than the average guy can ever dream of. It doesn’t matter if you are a young heart-throb or a past-your-prime senior citizen. If you are a star then you can fulfill your lustful fantasies.

There is an obvious double standard that exists though. If you are a male star that is running around town with a new girl every night then you are considered a stud. If you are a woman that does the same thing then you are referred to in more colorful and less flattering terms. These derogatory monikers have been applied to such female celebrities as Kim Kardashian, Paris Hilton, and even Taylor Swift. Female celebrities canoodling with multiple men is nothing new. Vintage starlets like Jean Harlow and Grace Kelly were notorious for their legendary sexual appetites and ever-changing partners long before today’s promiscuous female personalities were at it. Here are the 19 female celebs who’ve hooked up with the most gents around Hollywood.

19. Angelina Jolie

Angelina Jolie is far from the most salacious character on this list but she’s still been around the block a time or two and with her new-found single status we can be sure that she will go around a couple more times before all is said and done. She was first married to Jonny Lee Miller from 1996-1999. During that time she was also apparently spending the night together with Mick Jagger, Timothy Hutton, and Jenny Shimizu. She then wed Billy Bob Thornton from 2000-2003 while at the same time being linked to Antonio Banderas and Nicolas Cage. She enjoyed the single life for a few years by hooking up with Val Kilmer, Jared Leto, and a guy you’ll see mentioned several times on this list, Colin Farrell. We then had Brangelina but that’s over now. Who’s up next?

18. Pamela Anderson

No list of Hollywood harlots would be complete without having Pamela Anderson on it but, believe it or not, her exploits are far tamer than most others on this list. She was discovered by accident when a cameraman at a football game in Vancouver zoomed in her as she sat in the crowd. She was seen on the Jumbotron and was immediately hired as a spokesmodel. This led to modelling which led to Playboy which led to bit parts in television shows and eventually to her breakout starring role in the Baywatch television series. She dated Mario Van Peebles, John Peters, Eric Nies, Scott Baio, David Charvet, and Vince Neil before marrying Tommy Lee of Motley Crue in 1995. After that marriage broke up she hooked up with Bret Michaels, Kelly Slater, Steven Dorff, some guy named Jamie Padgett, and Criss Angel. She also managed to squeeze in a short romance with Kid Rock. After marrying and divorcing Rick Salomon in 2015, Pamela is looking for her next conquest.

17. Eva Longoria

42-year-old Eva Longoria landed a few bit parts on television beginning in 1999 before she got her big break with her role of Gabrielle Solis on Desperate Housewives. She has since appeared in dozens of movies and television shows as well as racking up a few producer credits. She’s also gone through quite a few different guys. Her first marriage to Tyler Christopher lasted from 2002 until 2004. She married Tony Parker in 2007 but that union fell apart in 2011 after the dark-haired beauty found several incriminating text messages on his phone. She is presently married to Jose Antonio Baston. She has also been in relationships with J.C. Chasez, Hayden Christensen, Eduardo Cruz, and Ernesto Arguello. She is rumored to have had a fling with Mark “Butt Fumble” Sanchez too.

16. Jennifer Lopez

J.Lo got some much-needed exposure as a Fly Girl in the television comedy In Living Color. She decided to pursue an acting career and she got a good break when she was given the lead in the movie Selena. She then began a recording career and she has never looked back. She is one of the most recognized faces in Hollywood. With all of the work that she does, it is hard to believe that she has found time to get involved with so many guys. She has been married to Ojani Noa, Cris Judd, and Marc Anthony but all of her marriages ended in divorce. She is presently dating Alex Rodriguez. She was once engaged to Ben Affleck but things didn’t pan out. Jenny from the block has tangled with Drake, Beau Casper Smart, Sean Combs, Wesley Snipes, and Chris Paciello as well as Maksim Chmerkovskiy, Bradley Cooper, and Rodrigo Santoro.

15. Lindsay Lohan

For someone who is just 30 years old, Lindsay Lohan has compiled an excessively long list of lovers. The ex-Disney starlet has been involved in relationships with both men and women including Aaron Carter, Jamie Dornan, Robbie Williams, and Heath Ledger. She has a soft spot for the older dudes as shown by her tumbles in the hay with Benicio Del Toro, Floyd Mayweather Jr., and Mr. Die Hard Bruce Willis. When she was in her early 20s she apparently had flings with James Franco, Jared Leto, Joaquin Phoenix, Jude Law, James Blunt, Gerard Butler, and Seth Rogen. Of course, Justin Timberlake, Criss Angel, and Colin Farrell got in on the action too as did Ryan Phillippe, Jason Segel, Orlando Bloom, and 50 Cent. There are literally dozens of Hollywood stars linked to LiLo. It’s not the size of the list that is so amazing as much as the fact that she hasn’t had any children yet.

14. Jada Pinkett Smith

This 45-year-old actress/singer/dancer saw her star rise in the early 90s with small television roles. She garnered a lot of attention when she was featured in The Nutty Professor in 1996. She began a singing career in 2002. She has been married to actor Will Smith for 2 decades but before she settled down with the Fresh Prince, Jada had romances with Tupac Shakur, Wesley Snipes, and ex-NBA player Grant Hill. She has described her marriage as “open”, which means that they both get to sleep around. There are also rumors circulating that Will is, in fact, bisexual and the marriage is in trouble. To add fuel to the fire, there were printed stories that Jada was caught in the sack with Marc Anthony. It is hard to separate the wheat from the chaff when it comes to the many rumors that surround this couple but the one sure fact is that it is a bizarre relationship.

13. Megan Fox

31-year-old Megan Fox is one the world’s biggest sex symbols. The actress and model landed bit parts in television before landing a role in the movie Confessions of a Teenage Drama Queen in 2004. Her big break happened in 2007 when she landed the part of Mikaela Banes in Transformers. She got hot and heavy with her co-star Shia LaBeouf. She also had relationships with Ben Leahy and David Gallagher in the early 2000s. In 2010, Fox married Brian Austin Green of Beverly Hills 90210 and Desperate Housewives fame. They have been together ever since.

Despite being in several relationships, Megan Fox maintains that she has had sex with just 2 guys and has never entertained the thought of a one-night-stand. Yeah, right. She has also hinted that she is bisexual.

12. Jessica Biel

Jessica Biel got her start in the television show 7th Heaven in which she cultivated a wholesome image in her role of Mary Camden. She has gone on to star in a string of movies such as Ulee’s Gold, The Texas Chainsaw Massacre, The Rules of Attraction, and Total Recall. She is currently filming her 33rd movie, Shock and Awe. Biel has been married to Justin Timberlake since 2012 and they have one child. Prior to settling down with JT, Jessica had her share of hot dates with the likes of Adam LaVorgna, Chris Evans, and Derek Jeter. We aren’t sure if the ex-Yankee left her a gift basket. It is also widely believed that she had a torrid romance with Gerard Butler as the two were seen cozying up in 2011.

11. Demi Moore

After her appearances in Blame it on Rio, St. Elmo’s Fire, and About Last Night…, Demi Moore became a household name. While she has been in a few flops, Demi has landed some great roles over her 30+ years in the business. She has landed her share of men too. The brunette married Freddy Moore back in 1980 but the two split after just 4 years. Moore and Emilio Estevez were engaged but they broke up in 1987 which led to her much-publicized marriage to Bruce Willis. That lasted 11 years before dissolving. She made headlines in 2005 when she married Ashton Kutcher but the fairy-tale romance ended in 2013. Demi has been intimate with many other guys like Dweezil Zappa, Brad Pitt, Owen Wilson, Tobey Maguire, and Alex Rodriguez among others. Of course, Colin Farrell got in there too.

10. Mariah Carey

This voluptuous diva has been in the spotlight for nearly 30 years and she has been the subject of many men’s fantasies. She may be in her late forties but she has maintained a bubbly and youthful appearance. Who cares if she has a good plastic surgeon? Mariah has put smiles on quite a few guys and we don’t mean with her singing or acting. She has been married to Tommy Mottola and Nick Cannon but she has a long list of others that she has been intimately linked to Christian Monzon, Mark Sudak, Erik Benet, and Mr. Gift Basket Derek Jeter. It is thought that she has hooked up with Eminem, Trey Songz and Stevie J. It has been reported that she is currently dating Bryan Tanaka. She sure gets around!!

9. Alyssa Milano

Milano hit it big in the 80s sitcom Who’s The Boss in which she played Tony Danza’s daughter, Samantha. She parlayed that role into a very successful career on the big screen as well as television. She’s also been around the block a couple of times when it comes to hooking up. She dated Kirk Cameron, Corey Feldman, Corey Haim, David Arquette, Jonathan Silverman, Eric Nies, Scott Wolf, Jason Behr, Jimmy Federico, Justin Timberlake, Brian Krause, and lots of others including Mark Wahlberg. She must have tired of actors because she began a string of relationships with Major League Baseball pitchers Carl Pavano, Barry Zito, and Brad Penny. She was briefly married to singer Cinjun Tate but that union lasted just one year. She is currently married to David Bugliari. Hilariously enough, she wore white on her wedding day.

8. Cameron Diaz

Vincent D’Onofrio, Carlos De La Torre, Matt Dillon, Robbie Williams, Justin Timberlake, Jude Law, Kelly Slater, and Keanu Reeves are just some of the Hollywood stars that Cameron Diaz has had a romantic involvement with. She has also been linked to Alex Rodriquez, Sean “Puffy” Combs, and Tyrese Gibson. There’s something about Cameron! The Charlie’s Angels star is rumored to have had flings with Seth McFarlane, Maroon 5’s Adam Levine, Gerard Butler, Bradley Cooper, Ed Norton, Djimon Hounsou, Vince Neil, and Mr. Magic himself, Criss Angel. The blonde was engaged to Jared Leto back in 2002-2003 but things just didn’t seem to work out and the couple went their separate ways. She finally settled down in 2015 when she married Good Charlotte guitarist Benji Madden in Beverley Hills. We’ll see how long that lasts before she starts adding more notches to her bedpost. She’s only 44 so she has plenty of time.

7. Halle Berry

Halle Berry has been a fixture on the big screen since 1991 when she was given a small part in Jungle Fever. She has been in dozens of movies since including the X-Men franchise, Monster’s Ball, and Catwoman in which she looked especially hot. She’s been involved in several relationships. She married baseball player David Justice in the early 90s. That romance made headlines after accusations of domestic abuse. The two split in 1997. The smoking hot Halle married Eric Benet in 2011 but that matchup ended with divorce. She entered into a 5-year relationship with Gabriel Aubry before getting married for a third time to Oliver Martinez. In between her marriage, Berry has been romantically involved with Kevin Costner, Wesley Snipes, Christopher Williams and several others. Rumor has it she got down with Eddy Murphy too.

6. Dolly Parton

When people think of Dolly Parton, the first thing that comes to mind is her titanic vocal chords that have been belting out hits for decades. The curvaceous country singer has been married since 1966. Her husband, Carl Dean, has kept himself out of the public eye and is rarely seen with Dolly. He tends to stay home while Parton is on the road. This opens a lot of opportunities for infidelity. Although Parton has maintained a clean image, she has admitted to straying. She just hasn’t named names but it is widely believed that she has had affairs with band leader Gregg Perry, Sylvester Stallone, and Burt Reynolds. She has denied allegations of a lesbian affair with her assistant Judy Ogle. She is also rumored to have been involved with Billy Ray Cyrus and is Miley’s Godmother.

5. Pink

Alecia Moore, otherwise known as Pink, hit the scene in 2000 with her debut album Can’t Take Me Home. As it turns out, you actually can take her home and several guys have. The animal rights activist and LGBT supporter may have settled down after marrying Carey Hart in 2006 but she got around before hooking up with him. Actually, she may still get around as the two are allegedly in one of those “open” marriages. She is rumored to have gotten it on with Motley Crue drummer and all-around bad boy Tommy Lee as well as Anthony Criss. Todd Morse got the party started with her and Pink has even been romantically linked to women. Apparently, it just took an ice cream cone for Joey Fatone to briefly win her over.

4. Jayne Mansfield

Here is another blonde bombshell that packed a whole lotta love into a very short period of time. Jane Mansfield was one of the biggest sex symbols of the 50s and 60s and she loved to flaunt her best assets. She was 21 years old when she appeared on screen in her first film in 1955 and her last role came in 1967 just prior to her tragic death. She did a lot more than movies during her 12-year run. She had lots of sex with lots of guys. Her first marriage to Paul Mansfield lasted from 1950 to 1958 but she also found time during this period to canoodle with Clint Eastwood, Steve Cochran, George Jessel, and a host of others. After another infidelity-filled marriage to Mickey Hargitay, she married Matt Cimber in 1964 but she soon ran off with her attorney. Colin Farrell would have really loved her.

3. Marilyn Monroe

Marilyn Monroe is probably one of Hollywood’s most famous sex symbols. She was just a teenager when she began modelling in 1944. This led to film work and she was soon a star. By the early 50s, she was all over the big screen in roles that cultivated her image as a blonde bimbo. Her off-screen life was legendary as she was romantically linked to dozens of powerful figures like Howard Hughes, mobster Sam Giancana, and John and Bobby Kennedy. She bedded an impressive roster of Hollywood actors like Frank Sinatra, Marlon Brando, Uncle Miltie, Dean Martin, and Yul Brenner. Robert Mitchum, Eddie Fisher, James Dean, and John Huston. She got it on her a few women too including Elizabeth Short, otherwise known as the Black Dahlia. She had dozens of intimate relationships before she died at the age of 36. Some like it hot. Marilyn sure did!

2. Joan Crawford

Joan Crawford is one of the silver screen’s biggest names ever. Her film career started in 1925 during the silent era and by 1930 she was one of the industry’s most recognizable names. She was in over 80 films over a 45-year span. She was also in over 80 relationships. She was married several times but she had all sorts of lovers on the side. Walter Winchel, Spencer Tracy, Rudy Vallee, Cesar Romero, Jackie Cooper, Humphrey Bogart, and Robert Mitchum are just scratching the surface. She even bedded Howard Hughes. You can also put down Claudette Colbert, Dorothy Arzner, Barbara Stanwick, and allegedly Marilyn Monroe as well. That’s right!! She liked women too. Other notable Hollywood heavyweights like Kirk Douglas, Cary Grant, and Gary Cooper found their way into her arms. She even straightened out Rock Hudson in 1953.

1. Tallulah Bankhead

Tallulah isn’t the most famous name on the list of 15 female celebs who’ve hooked up with the most gents around Hollywood but she might be one of the most notorious sex fiends. She appeared in many Broadway shows, movies, and on television. She is also well-known to have had an insatiable sexual appetite that led to numerous encounters with some of the most famous men and women in Hollywood. She was involved with no less than 68 partners including Errol Flynn, Louis Armstrong, Yul Brynner, Groucho Marx, Burgess Merideth, and Humphrey Bogart as well as Jimmy Durante, Chico Marx, John Barrymore, and Douglas Fairbanks. She is even rumored to have had a fling with Winston Churchill. She was married between 1937 and 1941 but, let’s face it, Tallulah wasn’t really a one-man kind of gal.

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