During the week in which Jeopardy! was hosting the IBM challenge, they brought in an avatar of Watson to do announcing duties, and Watson immediately started sucking up to Conan. When Andy called him on it, Watson started talking about how his wife prefers him (Watson) in bed— and Andy pulled a baseball bat out from behind his podium and started beating the shit out of Watson. Sparks were flying and everything, while the crowd chanted "ANDY! ANDY!"
Watson returned the following day, and this time Andy blasted him with a shotgun.
Watson also returned on the third day. Andy then grabbed him, ran to the roof and threw it on to the empty parking lot below. And then it blew up.
Conan: Why did they pack a computer screen with explosives?
Steven Ho's segments. So far on TBS he's cut a watermelon resting on Conan's chest with a katana, attacked Conan with the same katana while blindfolded (teaching Conan to dodge), broken staves on Conan, and had Conan break boards and concrete blocks.
Both Funny and Awesome: The last show of Chicago week featured a segment at Chicago's famous Weiner's Circle. Jack Mcbrayer, traumatized by the vulgar staff, vows to return with a friend. He returns with Triumph the Insult Comic Dog, who proceeds to give it back to the staff to the point where he's finally allowed to join them behind the counter.
Paramore was supposed to be the musical guest on Conan, but during rehearsal on that same day, Hayley Williams blew her voice out and had to be taken to the hospital, meaning Paramore had to suddenly cancel. What did Conan do? He decided to be his own musical guest, singing and playing guitar with the band. And it was glorious.
One for one of Conan's guests: Emmy Rossum told a story from her childhood, of training as an opera singer, and getting free hot dogs from the local deli if she would sing for them. Conan produces a hotdog, Emmy sings an aria which renders Conan and the audience completely speechless. And she got to eat the hot dog.
Andy Richter got one when Chelsea Handler stopped by; she asked Conan and Andy if they liked the ocean, and when Andy said he did, she asked if it made him float (an obvious dig at his size.) Richter took a moment, and then responded "Yes. Do you sink with your cast-iron heart?" Cue massive audience applause.