Former Mr. Jessica Simpson John Mayer is surrounded by a bevy of beautiful men while Cosmopolitan honored him as fun fearless male of the year at NYC’s Cipriani on Monday.

Mayer, 30, is seated between actor pal Dave Annable and rapper/actor Common. Behind them are Canadian animal trainer and zoologist Dave Salmoni, Dirty Sexy Money actor Peter Krause, MySpace founder Tom Anderson, The Office star John Krasinski, funny man Dane Cook and the current reigning Mr. Jessica Simpson, QB Tony Romo.

“I was thinking, you have John Mayer, Dane Cook,” Romo said as he accepted his award for being fun and fearless. “If you date Jessica Simpson, I guess you’re fun and fearless.”

Pictured inside: Carmen Electra and singer/songwriter Sara Bareilles.

45+ pictures inside of Cosmo honors John Mayer… More Here! »

Gap has regularly used celebrities to sell their clothing to the public. This Fall, Gap is once again relying on the power of celebrities to sell their styles and looks. Featured in this Fall’s Gap ads are Chris Evans (Fantastic Four), hip-hop artist Common, supermodel Eva Herzigova, Jeremy Piven (Entourage), Mia Farrow, Natasha Bedingfield, Pete Wentz (Fall Out Boy), and Piper Perabo (Cheaper By The Dozen, Coyote Ugly).

 - Doobybrain