My feelings about Gilmore Girls are complex and ever evolving, but it’s very fun when I get to say, “Hey! Look at that!” In the case of season four, episode 4, it’s (depending on your reference point) Sherriff Leo from Veronica Mars, or Schmidt from New Girl.
Here he plays a guy named Luke who is at Dean’s bachelor party. The guy in the sailor suit standing next to him is Chauncey Leopardi, who played Alan White on Freaks and Geeks (among other things). He has a couple of very funny scenes in Gilmore Girls.
I also saw Rami Malek in an episode of Season 3.