Well, Shatner in the original Star Trek... let me put it this way. There's a graphic out there on the Interwebs with a picture of original-series!Kirk, sitting there and beaming, and the caption reads, "I'm sorry; I can't hear you over the sound of how awesome I am." So I imagine Damon could definitely play somewhat over-the-top, overconfident hotshot. Like rivendellrose said, it wouldn't be that far removed from his character in Dogma. Or some of his personas in The Talented Mr. Ripley