11. Joey Tribbiani, Friends (1994-2004) and Joey (2004-2006)
Played By: Matt LeBlanc
Hottest Conquests: Janine Lecroix (Elle Macpherson), Rachel Green (Jennifer Aniston)
For all the bluster that is paid to Joey Tribbiani's womanizing ways—what with his signature "How you dooiinn?" pickup line—not a lot of airtime was devoted to actually seeing the dumb but lovable struggling actor with a woman. And those episodes that did usually showed him being way more into the woman than she was into him. And on more than one occasion, Joey's girlfriends seemed more interested in one of his fellow "friends" altogether.
But he did end up landing Rachel (Jennifer Aniston), if only for a fleeting moment. Which makes him a winner in our book.