The Dirty Dozen: Hollywood's Naughtiest Bachelors

John! Leo! Brody! See how these notorious playboys make being bad look so good

01 of 12

JOHN MAYER

JOHN MAYER
Anthony/Pacific Coast News

Jessica Simpson, Minka Kelly and Jennifer Aniston have all been spotted on his arm, but nobody has been able to capture the troubadour's heart – yet! What's Mayer's secret for attracting the ladies? "He makes you feel like you're the most beautiful woman on the planet," a source told PEOPLE. Obvious charm aside, in a recent poll, 70% of PEOPLE.com readers said they wouldn't date the musician.

02 of 12

LEONARDO DICAPRIO

LEONARDO DICAPRIO
Ramey

He recently split with girlfriend Bar Refaeli because he wasn't interested in a serious commitment. ("She wanted to move in together," a source told PEOPLE in June). But the actor is true to his longtime friends: The low-key clubgoer recently enjoyed a night out at H.Wood with his posse of single pals (and some female admirers), and is also a fixture courtside, cheering his beloved Los Angeles Lakers with his buddies.

03 of 12

BRODY JENNER

BRODY JENNER
Will Binns/Pacific Coast News

The Hills star has charmed everyone from Lindsay Lohan to Kristin Cavallari – and he once boasted to PEOPLE about his way with the ladies, "On a plane, I picked up a flight attendant from Canada!" But these days, he's been spending time with his girlfriend Jayde Nicole, Playboy''s 2008 Playmate of the Year. Still, that hasn't kept him out of the clubs – or away from his wingman, Frankie Delgado.

04 of 12

JAMIE FOXX

JAMIE FOXX
Kevin Mazur/WireImage

He just shared a super-smoldering liplock with Halle Berry at the Spike TV 2009 Guys Choice Awards – but that was just for show. A fixture in the clubs, the actor-singer (who scored a Top 10 hit with the single, "Blame It (On the Alcohol)") loves to share his alcohol – especially vodka – with female clubgoers ... sometimes even pouring it into their mouths straight from the bottle!

05 of 12

BRET MICHAELS

BRET MICHAELS
Bill McCay/WireImage

His primary gig may be fronting the band Poison, but these days the rocker makes his living looking for romance on his debauched VH1 reality show Rock of Love. Already three seasons in, Michaels hasn't found true love yet – but then again, he's not looking all that hard. "I'm pretty honest with the girls," he told PEOPLE about his dating philosophy. "I tell them, 'Look, we're dating. There's no white picket fence.' "

06 of 12

JOSH HARTNETT

JOSH HARTNETT
Gareth Cattermole/Getty

The actor has enjoyed his pick of famous women – including on-and-off girlfriend Helena Christensen. And in March, the actor was spotted locking lips with former flame Kirsten Dunst. The next month, though, he was hitting the clubs (solo!) – just a week after being hospitalized with a stomach ailment. Now that's a devoted bachelor!

07 of 12

JEREMY PIVEN

JEREMY PIVEN
David Goldman/AP

Nothing can keep this bachelor down – not even a case of mercury poisoning. Before bowing out of Broadway's Speed-the-Plow due to sushi-related illness, Piven was spotted partying into the wee hours in New York City. Although the producers of the show have since disputed Piven's reason for leaving, he isn't letting a little arbitration hearing get in the way of romance; He was recently spotted having a "lovey dovey" dinner with Marina Katz – who once dated Michael Phelps!

08 of 12

DIDDY

DIDDY
Seth Browarnik/Startraks

He's stayed close to ex Kim Porter, the mother of his 2-year-old twin girls D'Lila Star and Jessie James and son Christian, 11, but Diddy famously declared in 2006 that he just wasn't ready for marriage. And he still hasn't settled down: This spring, the music mogul overshared details about his active love life, posting on Twitter, "Having tantric sex!!!! I feel so much better.!!! Thank you." TMI!

09 of 12

KEVIN CONNOLLY

KEVIN CONNOLLY
Chris Weeks/WireImage

Just call him Leo's wingman! The Entourage star – who has dated Nicky Hilton and was linked with Haylie Duff at one time – is an avid clubgoer, making the scene with pals like Lukas Haas at hot spots like

Crown Bar and Hyde.

10 of 12

MICHAEL PHELPS

MICHAEL PHELPS
Most Wanted/Flynet

The Olympian raced into the spotlight – and the VIP lounge – after his 2008 triumph in Beijing. And while he may not consider himself a sex symbol, that hasn't stopped him from partying with a bevy of eager women. A favorite spot? Prive Las Vegas, where the swimmer hung by the deejay booth and got affectionate with a brunette while enjoying Sin City's nightlife with pals.

11 of 12

GERARD BUTLER

GERARD BUTLER
Bauer-Griffin

Once linked with Dancing with the Stars pro Cheryl Burke and even Shanna Moakler briefly, the Scottish hunk (who was included in 2008's Hottest Bachelor issue) has his own novel approach to picking up women: He draws attention to his buff bod, joking that his favorite (faux) pickup line is, "Have you seen 300?"

12 of 12

KANYE WEST

KANYE WEST
Gabriela Maj/Getty

"Women go crazy over him," his pal Emmanuelle Cuny-Panicker once told PEOPLE. "We went out two weeks ago and the girls were almost knocking me over to get to him." And until recently, the rapper's been a one-woman kind of guy: He ended his engagement to Alexis Phifer only to start exclusively dating model Amber Rose (they've since split). Now single, West is free to fulfill one of his dreams – to pose in the buff. As he told Vibe, "I definitely feel like, in the next however many years, if I work out for two months, that I'll pose naked."

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