Players' Club: Men Who Have Been Around the Block

Breezy, Weezy, Ray J and more guys who ain't loyal.

I Get Around - While monogamy has been the trend in Hollywood these last few years, some guys just can't be pinned down. Here's a rundown of stars notorious for playing the field.(Photos from left: Prince Williams/WireImage, Julien Hekimian/WireImage)

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I Get Around - While monogamy has been the trend in Hollywood these last few years, some guys just can't be pinned down. Here's a rundown of stars notorious for playing the field.(Photos from left: Prince Williams/WireImage, Julien Hekimian/WireImage)

Photo By Photos from left: Prince Williams/WireImage

Chris Brown - Our list of men who get around starts with — who else? — Chris Brown. It was bad enough when Breezy was bouncing back and forth (and back, and forth) between Rihanna and Karrueche Tran, but when news broke he fathered a child with Texas-based model Nia Guzman, it became clear that this bro ain't loyal.  (Photo: Kevin Winter/Getty Images for iHeartMedia)

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Chris Brown - Our list of men who get around starts with — who else? — Chris Brown. It was bad enough when Breezy was bouncing back and forth (and back, and forth) between Rihanna and Karrueche Tran, but when news broke he fathered a child with Texas-based model Nia Guzman, it became clear that this bro ain't loyal.  (Photo: Kevin Winter/Getty Images for iHeartMedia)

Lil Wayne - Women are right up there with guns, liquor and luxury goods among hip hop's biggest muses, and a quick study of Weezy's lyrics prove that he is deeply inspired by the ladies in his life. From Toya Wright to Lauren London and Nivea, Trina and, most recently, Christina Milian, Tunechi has spread his love far and wide.  (Photo: Kevin Winter/Getty Images for BET)

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Lil Wayne - Women are right up there with guns, liquor and luxury goods among hip hop's biggest muses, and a quick study of Weezy's lyrics prove that he is deeply inspired by the ladies in his life. From Toya Wright to Lauren London and Nivea, Trina and, most recently, Christina Milian, Tunechi has spread his love far and wide.  (Photo: Kevin Winter/Getty Images for BET)

Wilt Chamberlain - The late NBA player was as well-known for his purported number of sexual conquests as he was for his baller stats. He wrote in his memoir that he slept with at least 20,000 women. Of course, someone out there did the math, and if Wilt was sexually active between ages 15 and 55 (when the book was published), that would mean he hit it with 1.4 women per day, every day. Amazing he had any time to focus on basketball! (Photo: Brian Bahr /Allsport)

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Wilt Chamberlain - The late NBA player was as well-known for his purported number of sexual conquests as he was for his baller stats. He wrote in his memoir that he slept with at least 20,000 women. Of course, someone out there did the math, and if Wilt was sexually active between ages 15 and 55 (when the book was published), that would mean he hit it with 1.4 women per day, every day. Amazing he had any time to focus on basketball! (Photo: Brian Bahr /Allsport)

Gerard Butler - The Scottish actor is best known for playing the lead in the swords-and-sandals epic 300, but that number could very well be referring to something else entirely. Butler is a well-known lothario around Hollywood, having hooked up with everyone from runway models to his co-stars and even the occasional reality star (lucky girl, Brandi Glanville!). The actor is now engaged to Morgan Brown, so hopefully his player days are behind him. (Photo: Saif Bakshi/Getty Images)

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Gerard Butler - The Scottish actor is best known for playing the lead in the swords-and-sandals epic 300, but that number could very well be referring to something else entirely. Butler is a well-known lothario around Hollywood, having hooked up with everyone from runway models to his co-stars and even the occasional reality star (lucky girl, Brandi Glanville!). The actor is now engaged to Morgan Brown, so hopefully his player days are behind him. (Photo: Saif Bakshi/Getty Images)

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Diddy - The Bad Boy boss has been with some of the most beautiful women in the business — from his baby mothers Kim Porter, Misa Hylton-Brim and Sarah Chapman, to superstars Jennifer Lopez and Cameron Diaz and now singer/model Cassie — without ever having walked down the aisle. He explained earlier this year that he doesn't believe in marriage, though he'd be happy to sign a "love contract" with anyone he's in a serious relationship with. Romantic! (Photo: Ethan Miller/Getty Images for SHOWTIME)

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Diddy - The Bad Boy boss has been with some of the most beautiful women in the business — from his baby mothers Kim Porter, Misa Hylton-Brim and Sarah Chapman, to superstars Jennifer Lopez and Cameron Diaz and now singer/model Cassie — without ever having walked down the aisle. He explained earlier this year that he doesn't believe in marriage, though he'd be happy to sign a "love contract" with anyone he's in a serious relationship with. Romantic! (Photo: Ethan Miller/Getty Images for SHOWTIME)

Ray J - Brandy's bro became an international star thanks to his part in a little film called Kim Kardashian Superstar — and he's not going to let anybody forget about his breakthrough moment. Ray J has dated around all over town in the years since, but he'll never forget the one he claims he hit first. Ray J is currently married to Princess Love. We'll see if he can stay faithful! (Photo: Jerod Harris/Getty Images for AMC Networks)

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Ray J - Brandy's bro became an international star thanks to his part in a little film called Kim Kardashian Superstar — and he's not going to let anybody forget about his breakthrough moment. Ray J has dated around all over town in the years since, but he'll never forget the one he claims he hit first. Ray J is currently married to Princess Love. We'll see if he can stay faithful! (Photo: Jerod Harris/Getty Images for AMC Networks)

Alex Rodriguez - The disgraced Yankee has been playing the field ever since his divorce from wife Cynthia in 2008, and he definitely has a type: think blonde and athletic. A-Rod has been linked with Madonna, Kate Hudson, Cameron Diaz, WWE star Torrie Wilson and, most currently, fitness model Erin Simmons.  (Photo: Tom Pennington/Getty Images)

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Alex Rodriguez - The disgraced Yankee has been playing the field ever since his divorce from wife Cynthia in 2008, and he definitely has a type: think blonde and athletic. A-Rod has been linked with Madonna, Kate Hudson, Cameron Diaz, WWE star Torrie Wilson and, most currently, fitness model Erin Simmons.  (Photo: Tom Pennington/Getty Images)

50 Cent - Fiddy's magic stick has been around the block a few times. While on a promotional tour for his latest album, Animal Ambition, he spilled the tea on his past relationships with Ciara, Chelsea Handler and Vivica A. Fox. He also revealed which celeb he regrets never having dated — Rihanna! Fif and RiRi both seem to be single right now, so maybe it's not too late. (Photo: Dimitrios Kambouris/Getty Images)

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50 Cent - Fiddy's magic stick has been around the block a few times. While on a promotional tour for his latest album, Animal Ambition, he spilled the tea on his past relationships with Ciara, Chelsea Handler and Vivica A. Fox. He also revealed which celeb he regrets never having dated — Rihanna! Fif and RiRi both seem to be single right now, so maybe it's not too late. (Photo: Dimitrios Kambouris/Getty Images)

Eric Benet - Halle Berry's ex started the "sex addiction" trend in Hollywood, giving a formal medical diagnosis to his habit of sleeping around. Though their marriage ended as a result of his philandering, Benet seems to have cleaned up his act in the decade since and is now remarried with three children. (Photo: Ben Horton/Getty Images for BET)

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Eric Benet - Halle Berry's ex started the "sex addiction" trend in Hollywood, giving a formal medical diagnosis to his habit of sleeping around. Though their marriage ended as a result of his philandering, Benet seems to have cleaned up his act in the decade since and is now remarried with three children. (Photo: Ben Horton/Getty Images for BET)

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Mike Tyson - The self-proclaimed "prostitution hunter" has tussled with a string of women outside of the ring, including Naomi Campbell, Kenya Moore and a whole bunch of non-famous chicks. He was even sent to prison for rape in 1992, which he has always denied. But it was his one-year marriage to Robin Givens that dominated headlines after she told Barbara Walters he habitually swung his punches in her direction when they were together. (Photo: Kevin Winter/Getty Images)

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Mike Tyson - The self-proclaimed "prostitution hunter" has tussled with a string of women outside of the ring, including Naomi Campbell, Kenya Moore and a whole bunch of non-famous chicks. He was even sent to prison for rape in 1992, which he has always denied. But it was his one-year marriage to Robin Givens that dominated headlines after she told Barbara Walters he habitually swung his punches in her direction when they were together. (Photo: Kevin Winter/Getty Images)

Charlie Sheen - The Two and a Half Men star makes no attempt to hide his love life, even when it involves multiple women at the same time. Sheen, who was married to Denise Richards and Brooke Mueller, was also one of Hollywood madam Heidi Fleiss's most famous clients. That should tell you everything you need to know.  (Photo: Jason Merritt/Getty Images)

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Charlie Sheen - The Two and a Half Men star makes no attempt to hide his love life, even when it involves multiple women at the same time. Sheen, who was married to Denise Richards and Brooke Mueller, was also one of Hollywood madam Heidi Fleiss's most famous clients. That should tell you everything you need to know.  (Photo: Jason Merritt/Getty Images)

Hugh Hefner - The Playboy founder is the most notorious playboy of them all, having dated as many as 13 women at the same time. Though Hef is now married — he is in his 80s, after all — he provided the blueprint for players of all kinds. (Photo: Charley Gallay/Getty Images for Playboy)

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Hugh Hefner - The Playboy founder is the most notorious playboy of them all, having dated as many as 13 women at the same time. Though Hef is now married — he is in his 80s, after all — he provided the blueprint for players of all kinds. (Photo: Charley Gallay/Getty Images for Playboy)