Scott William Winters
Then: Ponytailed Harvard punk who gets a rhetorical beat-down at the Bow & Arrow Pub from Damon’s character; Damon then steals his girl and smacks him again before crossing back over the river: Southie 3, Barnies 0.

Now: Winters lost the ponytail for his role as Cyril O’Reily on HBO’s "Oz," but dug out his scrunchy for 2001’s "Jay and Silent Bob Strike Back," where he reunited with Damon and Affleck to parody the "Good Will Hunting" scene for their good buddy, director Kevin Smith. Yes, he likes them apples.