With all the temptation celebrities every day, it’s not surprising that a lot of them cheat. However, there are those who are notorious for always having a chick on the side, even if they are seemingly happy with their main chick. Here are 5 of the biggest culprits.

1. Lil Wayne

Lil Wayne

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Lil Wayne has never been one to stick with a girl for long. In fact, he’s known for breaking up with his many girlfriends, and sometimes not even waiting till breaking up before he starts seeing someone else.

After breaking up with Karrine “Superhead” Steffans, Weezy has been busy. He got his hands on the superhot Christina Milian, and even she wasn’t enough to make him faithful. He left her for the aspiring hip-hop vixen and model, Queen Sylver–who was Milian’s friend.


2. Future


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The rapper cheated on Ciara with his stylist, Tyrina Lee. He bought her expensive designer clothes and first-class tickets and continued seeing her even as he got Ciara pregnant with their son. Now that’s the perfect definition of a no-good man.


3. Chris Brown

Chris Brown

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Before beating her up, Rihanna was his main chick. Then they broke up, and he started dating Karrueche Tran. Then Brown made up with Rihanna and turned her into his side chick–Tran soon found out, and Brown and Riri had to stop seeing each other.

But that wasn’t enough for the singer; he cheated on Tran again with one of her friends, Nia Amey. And he even got her pregnant.


4. Kobe Bryant


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Kobe’s wife, Vanessa Bryant, is tough. Very tough. She’s stuck with her man even as she discovered that he’s not a nice person. Even though they met and got married while she was still a teenager, it’s only her loyalty that has kept them together.

If the rape allegations against Kobe weren’t enough, he also slept with lots of other women over the years. He begged for forgiveness, but it’s quite likely he’ll cheat again.


5. Tiger Woods

Tiger Woods

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Golf is a sport whose stars are decent and respectable. That is, until Tiger Woods came into it. The guy had so many side chicks that every day after we learned of his infidelity, a new girl came out and said she was his side chick.


6. John Mayer

John Mayer

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We all know John is a major hottie, but he is also allegedly a lady in the streets and a freak in many beds. He Cheated on Katy Perry with Kelly Monaco, but that wasn’t his first time. He is known for his cheating ways, just a bad boy that breaks hearts.


7. Mathew Knowles

Mathew Knowles was married to Tina for 31 years however they divorced after Mathew had a child out of wedlock. There have been multiple reports of his cheating ways and if that were not enough he has been back and forth to court for child support of his son he had with his mistress Alexsandra Wright.


8. Jesse James

Jesse James

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After his split with Sandra Bullock for cheating he cheated on the woman he moved on with 19 times. Yep Kat Von D reported that Jessie had 19 women when they were together. He is the MVP of cheating!


9. Shaquile Oneal

Shaquille Oneal

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Shaq admitted that he was a guy and a guy with too many options. He may have thought that that was a joke but after a very expensive divorce and splitting up his family that included 4 children, he has realized the error of his ways.

9 Celebrity Cheating Men Who Always Have A Side Chick


These 9 men always have a chick on the side and have been known to be perpetual cheaters. Check out our list from some famous celebrities.

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