Made of Honor (2008)
If you take Julia Roberts' character in My Best Friend's Wedding and turn her into a man, then you'd get Dempsey's Tom in Made of Honor. Tom's your typical and cliché man-about-town who's suave, lives in a posh bachelor pad, and has ladies offering up their digits right and left. That all goes down the drain, of course, when he realizes he is in love with his newly engaged best girl pal (Michelle Monaghan) and must find a way to stop her wedding.
Awkward nerd to hunky man in love: As ''Made of Honor'' hits DVD shelves, we thumb through the actor's diverse resume