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I was pretty sure Conan had Bono on. I don't remember if he was the musical guest but I remember Bono sitting in the guest's chair next to Conan. Bono goes into how he's either a born again Christian or being celibate, something like that. Conan takes out an acoustic guitar and tells Bono he wrote a song for him and he's not that good but he'd like Bono's critique of it. Conan starts singing a song about Bono's celibacy and how much it could affect him. It gets more and more blatantly offensive. One line he has talks about Bono's "gonads on a shelf" Bono starts objecting to these lyrics and interrupting the song but Conan tells him listen, just listen to the whole thing, I promise to wrap it up in a classy way. But Conan actually keeps making it worse and worse, culminating in him singing antagonistically "You'll always be horny! You'll always be horny! You'll always be horny and you'll never have sex!" By this point Bono gets up from his seat and chases Conan around the set angrily before they cut to commercial.
This was somewhere between 1998-2002 and teenage me thought it was hilarious. I also seem to remember Conan doing almost this same exact bit with one other guest which tipped me off that all the guest reactions were indeed scripted.
I don't remember anyone ever speaking of it again or seeing any clip of it. Does anyone know of any clip of this existing or remember any of it? Could it be that I had the guest wrong and it wasn't Bono but maybe some other dude with sunglasses and slicked back hair?
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