Chad Michael Murray
Role: Tristan Dugray
Episode: Various episodes in seasons 1 and 2
Chad Michael Murray's very first reoccurring role was that Chilton's resident bad boy: Tristan. For two seasons he had a love-hate relationship — okay, mostly hate with just a little bit of love — with Rory before moving on to shows like Dawson's Creek and One Tree Hill.
Episode: Various episodes in season 7
Having already been on Veronica Mars, Lucy was just her second recurring role. She graduated Yale with Rory and moved on to star in Don't Trust the B---- in Apartment 23.
Role: Dave Rygalski
Episode: Various episodes on season 3 and 4
Before becoming geeky teen heartthrob Seth Cohen on The O.C., Adam Brody caught the eye of one Stars Hollow resident: Lane Kim.