Kenny Chesney brags that he’s slept with over a hundred women

Country singer Kenny Chesney has been the subject of gay rumors for years. It didn’t help when his marriage to Renee Zellweger ended after just a few months, with both parties agreeing on “fraud” as the cause. Chesney, 40, attempted to set the record straight, so to speak, in a new interview with Playboy. He said that he’s slept with over a hundred women, as if his skeevy promiscuity proves that he’s heterosexual. Chesney also talked about his brief marriage to Zellweger, and admitted that he still thinks about her every day and feels bad for pushing her out of his life when he realized it wasn’t going to work:

Kenny Chesney tells Playboy magazine that he’s definitely not gay and has well over 100 women who could attest to that.

“Man, I was over 100 several years ago,” he tells the men’s magazine for its March issue out Friday. “There were years when I had a better summer than A-Rod, buddy. You know? I got on the boards quite often.”

In the Q&A interview, the singer also discusses his 2005 marriage to actress Renee Zellweger, which was annulled after four months.

He said he “didn’t have any clue as to what true marriage meant. I was so used to committing to one thing — music — and then I had to totally commit to a second thing, marriage. I didn’t know how to commit to both of them.”

He also told the magazine that the paparazzi and attention became too intense. “I mean, I panicked, there’s no doubt about it. I just totally panicked,” he said, adding that he did “the only thing I knew to do: I ran. I pushed her away.”

Chesney said he called for an end to the marriage, but she filed the annulment papers. “It was a pretty mutual thing, to be honest with you,” he said.

After the breakup, he was depressed and didn’t leave the house or get out of bed for a week. He said he spoke with Zellweger on the phone briefly about a year ago but admits, “I still think about her every day. Every day I wonder if she’s OK.”

To have the marriage annulled, Chesney said the legal papers could claim either physical abuse, mental abuse or three or four other things that weren’t true.

“The best thing we could put in there was fraud. So I said ‘All right, do it. Whatever,’” he recalled.

[From AP via WSBT]

Chesney explained the large number of women he’d bedded as a kind of feast after a famine. He said he reached triple digits in 2001 and that “My first five years on the road were intense because I was the guy in college who never got laid until I started playing guitar… I’ve got a long line of girls who could testify that I am not gay.”

The hard working country star claimed he’s “pretty confident in the fact that I love girls.” If that’s the case then why does he have to talk numbers? That’s immature to say the least. As Queerty mentions he “doth protest too much.” I also like Shakespeare’s Sister’s take on this “Chesney asserts his heterosexuality via misogyny, because the best way to prove you ‘love girls’ is by treating them like shit.”

In November of last year Chesney brought Miss Tennessee 2005 Amy Colley to the Country Music Awards, and it came out that he’d been seeing her for several months. He was linked in the summer of last year to another pageant winner, Miss West Virginia 2008 Skylene Montgomery, after meeting her at one of his concerts.

How are his girlfriend(s) supposed to feel when they hear that he’s slept with over a hundred women? Maybe he’s not as much of a hound dog now, but they’ve got to wonder if he’s still slutting around with groupies considering how they met him. That’s not something you say when you’re planning on settling down with one woman at some point, but it doesn’t seem like that really interests Chesney. It’s also something that’s got to hurt Renee Zellweger considering that she was married to him in 2005, well after he passed the hundred mark.

Kenny Chesney is shown on Good Morning America on 10/14/08. Credit: WENN

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46 Responses to “Kenny Chesney brags that he’s slept with over a hundred women”

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  1. SolitaryAngel says:

    Poor sad thing. Does he REALLY think he’s fooling anyone?

    Verdict: SO gay.

  2. Livia says:

    OMG I’ve slept with 100 women, too! Also, I’m a princess.

    (see how easy it is to lie?)

  3. geronimo says:

    Gay and a bit of a tool. How did someone like Renee Z ever get involved with this? Lucky escape I say.

  4. snappyfish says:

    if someone says you are gay and you are not, why would one feel the need to address the fallacy at all. Then exclaim to the world your many many heteosexual conquests.

    Thou protest too much a la Tom Cruise.

  5. Syko says:

    I don’t know how he even got one, because he’s not attractive and as his latest statements prove, not intelligent or nice.

  6. DLR in Canada says:

    Ewwww, how tacky. I’m not impressed.

  7. jay walk says:

    I’d really like to see him without his cowboy hat for once.

  8. Syko says:

    @ jay walk – no you wouldn’t. Not impressive.

  9. Leni says:

    If he slept with 100 women, okay I buy that sort of. If he is claiming to have sex with 100 women, 2 was when really really drunk and the rest must have been drag queens. Be like Ricky Martin and just leave the subject alone.
    Jeez, liar, liar pants on fire.

  10. Roma says:

    Yes, because we’ve never seen gay men try to assert their sexuality by bedding tons of women before.

    I had a guy friend who had slept with well over 200 women… and he finally came out last year.

  11. Shannon says:

    A gay man could have sex with over 100 women and still be gay. It’s not like you’re suddenly unable to perform just because you’re gay. Yeah, it might be harder to get into the mood, and you’re probably not going to be attracted to the woman you’re having sex with. But you can still do it. Especially if you’re self-loathing and trying to prove to yourself and the world that you’re not gay.

  12. Hel says:

    Why do men feel the need to say this stuff? It just makes you look like a dumb slut – or, of course, you have something to hide!

  13. PJ says:

    Wonder how many STD’s he’s had?

    Seriously, though, maybe he’s had sex with hundreds of women, but how many women has he had a real relationship with? These were probably hookups with groupies he met on the road. He may think he “loves” women, but how much can you know about women in a series of one-night-stands when he probably didn’t even know their names?

  14. Ellen Smith says:

    100 women? He’s still no Wilt Chamberlain.

  15. Feebee says:

    Me thinks he protests too much.

  16. Sarah says:

    What’s the thing with semi-famous, highly ugly men to state how many chicks they had??? What’s going through their minds? Are those two brain cells responsible? Sometimes rubbing together to spark these thoughts and release them to the public?? What the frak?

  17. Baholicious says:

    Yeah, but did he ‘go down…’ That’s the barometer of straight, my friends.

    “(He’s) here, (he’s) queer! (He should) get used to it!”

  18. kate says:

    *ping pin ping pingpingping…*

    that’s the sound of my gaydar going off.

  19. mE says:

    Who gives a damn who he’s stuck it in? It always sounds skeevy when someone gives numbers. I guess he didn’t say that he actually didn’t have the sort of sex with these women he could have been having with a guy.

    Dude sounds like he is trying to convince himself.

  20. breederina says:

    Baho, we call that worshipping at the altar, and I agree it’s usually a pretty good litmus test for how much a person really loves the ladies. As for Kenny Cheesey, he may have slept with all of them but I doubt he had sex with any of them.

  21. BluePlanet says:

    Yes, but how many were intoxicated country music groupies after a show? Yes Kenny, you are such a stud.
    I’m convinced that men who brag about ‘how many’ are guys who couldn’t get just one woman to sleep with him more than once so they have to keep finding new ones.

  22. Diva says:

    Oh. my. GOD. Baho, lmao…

    My first husband was pretty, pretty, PRETTY… I mean, the guy is gorgeous.. AND he had slept with nearly 100 women (and he was only 26)… but absolutely REFUSED to “worship at the altar” (thanks breederina!)… then, one time, I found a pair of women’s underwear crumpled on the bathroom floor and accused him of screwing around, after hours of arguing, it finally came out that HE WAS WEARING THEM under his boxer briefs… we divorced a year later.

    He’s not out of the closet, but my ex-husband is SO gay, isn’t he????

  23. Christina says:

    the posts on this thread were really hilarious :)

  24. Ruffian9 says:

    So, he’s definitely gay then.

  25. Codzilla says:

    Diva: LOL! I apologize for being amused, because I’m sure it was an incredibly difficult time in your life, but damn, it must make you chuckle looking back. Anyway, it’s hard to imagine a straight man wearing panties, but I dunno, maybe he had some weird fetish thing going on? Either way, probably a good thing you two parted ways!

  26. Diva says:

    LOL… don’t worry codzilla, lol… I’m definitely laughing! Well, NOW! Now I have a MAN who worships me completely… heh heh… LOL… so I’m good!

    I think I knew with the ex, lol, but reading this story and thread made me really, REALLY know!

    Sadly, he’ll never admit it.

  27. bjf says:

    So he’s 40. Let’s say, for the sake of argument, he started having sex at 20 and he says he reached a 100 a few years back. That’s less than a sexual partner a month. For a famous guy out on the road – that’s nothing!!!

  28. RUTI says:

    Dumb..dumb..dumb.. Very good publicity, Kenny. I think he just wants to take himself out of “Entertainer of the Year” awards. He’s getting them without much talent anyway….

  29. TinaWithPom says:

    Ya know what I think about Kenny Chesney’s incredibly asinine “revelations”?

    “The man’s all hat and no cattle.”

  30. Vanna says:

    What male Singer or Star hasn’t slept with hundreds? It’s the fast pace life they lead. All we can hope is they have safe sex. Everyone knows they all do it, It’s the fame! Don’t sit and judge him for it! 80% of men would do the same if they were in his shoes. Leave the poor guy alone! If your attacked all the time your instinct is to fight back. You ignore it for awhile and when it doesn’t stop fight back!! I have a hard time understanding why people get off on hurting others. Kenny seems like a nice guy and he is a great entertainer. You can tell he loves his music and some people only have room for one love in their lives.

  31. Amanda says:

    I don’t know why I feel the need to put in a comment, but here it goes. Kenny Chesney isn’t gay. I know this for a fact. As for how many women he slept with I am not surprise by this. Hello he’s hot, can sing and famous there aren’t many women who wouldn’t give an arm for one night. I am shocked that he would actually give a number, but then look who was interviewing him. If he would have said he slept with ten women most of you would have found that as a reason to call him gay. The man can’t win either way.

  32. daisy424 says:

    @Diva, OMG, I am crushed. Your ex husband is gorgeous, really??

  33. Diva says:

    LMAO @ Daisy… that looks like you’re asking me if my ex-husband really is gorgeous…. you’ve seen pics, you know! lol

    And yes, REALLY… LOL

  34. daisy424 says:

    Sorry for the confusion Diva,I should have worded that better.
    I have seen his pics, shirtless too, just shocked and maybe a bit intrigued…..

  35. DM Pete says:

    I could care less what his sexuality is, he puts out great music and has a great voice. I didn’t ever planning on being 101, soooooo who cares! Just let the man sing. It’s his passion!

  36. Nanette says:

    Why doesn’t anywone think that his ex wife might be a lesbian? Hello, she’s not exactly out there with a steady boyfriend. Maybe Kenny’s concetrating on his long career. Rene did not get me at hello! : )

  37. Ted says:

    Couple of things. I’m a heterosexual male. I don’t think it’s 100% effective but I can call on gaydar when necessary. That is, I can often spot a gay guy. I say it’s not 100% effective because I’m sure there are guys who are gay who are difficult to detect. What I AM saying is there are guys who are gay who are NOT difficult to detect. Go back up there and look at Kenny’s picture. You can’t always judge a book by it’s cover but sometimes you can.

  38. Kari says:

    being a skeeze doesnt make you

  39. Rita says:

    HA!!! Yeah, right. And I’m the Queen of England.

  40. Vicki says:

    Kenny if I were you I would not address this issue anymore. People are joking here now. You are only hurting yourself. No one needs to know everything about you. Let it go. There are a lot of people who get married and it doesn’t work out. You were too busy in your career. Stop being so hard on yourself and let it go.


  41. chuky says:

    Ilove this singer his hansoman a perfect body his perfec boy

  42. aaslyn says:

    If he says he isn’t then he isn’t.He’s a great entertainer and his sexuality really is his business.For goodness sakes people, get a life and just enjoy his music.