One of Conan’s earliest guests was none other than the Governator himself, Arnold Schwarzenegger, who in the mid-’90s was still best known for his bodybuilding skills and funny laugh. The two have enjoyed a love-hate relationship ever since Conan revealed his flabby physique in the form of an almost nude cardboard cutout in a desperate bid for fitness tips. When Schwarzenegger points at Conan’s paper crotch and laughs before moving on to the host’s “girlie breasts,” Conan puts his foot down: “Arnold, when you make fun of my boobies, you go too far.”
But on those occasions when Conan couldn’t score an interview with the Austrian hunk, he was forced to improvise. Thanks to the wonders of green-screen technology, all Conan had to do was grab a still photo of the Terminator star, insert a green-screen mouth and — voilà! — pseudo Schwarzenegger! (Conan pulled the same stunt with Bill Clinton during the Monica Lewinsky scandal: “I’m gonna testify!” ol’ “Billie” bellowed). Fiction met reality in 1999 when Conan introduced the real Arnold to the “fake” one. “I knew you were going to do that. Look, I know you too well. I watch your show all the time. It’s one of your old tricks,” Schwarzenegger says before asking Conan to stare into the camera and sit very still.
What follows is one of the most hilarious impressions of O’Brien ever, especially the part when Arnold says on Conan’s behalf, “I’m a little girlie man. I’ve never had sex before. I have these beautiful breasts.” Saucy Governator.
(Also noteworthy: the Governator chit-chatting with ex-governor Rod Blagojevich.)