Conan O'Brien kicked off his week of Chicago tapings Monday night with a visit from Jack McBrayer, who got his start in comedy at Chicago's famous Second City.

The two covered it all, from trying to lose the Southern accent (McBrayer is decidedly unable to do it), to accidentally happening upon Chicago's naked bike parade outside of an Urban Outfitters.

All in all, O'Brien and McBrayer's endearingly antagonistic relationship makes for a fun interview, and the highlight might just be the fact that Conan hunted down and found McBrayer's caricature on the wall at Second City.

Watch the full clip above, and then check out part two of the interview, where McBrayer talks about being a waiter at a restaurant called Po' Folks, here.