Apparently, he played a game of "Shag/Marry/Kill" on Howard Stern's show years ago and the guy he opted to "Kill" was mad at him for nine years.
"I've found that there's never ever any good outcome to this," he said and simply refrained from answering.
The late-night host was otherwise very forthcoming, from talking about guests he'd never want to have on the show to the silly reason Barbra Streisand cancelled on him.
And Andy totally knew who he was talking about before saying anything, and it was all about whether or not he would rearrange his seats to accommodate a guest's "good side," as Cohen admitted he'd done four times for Mariah Carey. Kimmel, on the other hand, refused.
"Was it Streisand?" Cohen asked.
"The condition was we couldn't talk about the fact that we'd switched around," Kimmel said. "I was just like, 'I don't see how that is going to work?'" And so ultimately, Streisand backed out of her appearance.
As for those guests we'll never see, both Cohen and Kimmel played this game with Cohen rattling off Omarosa, Rams owner Stan Kroenke, Tucker Carlson and Danielle Bregholi, who he referred to as the "Cash Me Ousside" Girl.
Kimmel fumbled a little on his list, though he agreed with Omarosa, adding the Trump boys and his most recent arch-nemesis Sean Hannity.
When a caller tasked him with saying three nice things about the Fox News host, through, Kimmel had very little trouble with the task, though he kept his thoughts very, very superficial.
"He's got a nice square jaw," he said. And after a pause he added, "He's not a bad-looking guy and I think he's tall."
Cohen wanted to know what he was thinking during his latest interview with Kanye West, when Kimmel challenged him on his Trump support in light of his criticism of George W. Bush.
"You know what was going through my head?" Kimmel said. "We've got some commercials we need to run and he's never going to stop talking."
Kanye has stirred up a lot of controversy since he came out avidly in support of Donald Trump, but Kimmel said he actually likes and respects him now. They certainly have one thing in common as Kimmel has courted his fair share of controversy.
One of the biggest criticisms he faces these days is callbacks to his time as a cohost on "The Man Show," a comedy show most remembered now for its pointless segment called "Girls on Trampolines" which was ... well, girls on trampolines.
Considered a paragon of a misogynist era, many use the fact that he was on that show to dismiss any criticism he makes against Trump today; especially when it comes to any allegations of sexual impropriety or misbehavior against the president.
So Cohen asked if Kimmel thought that a show like "The Man Show" could even possibly survive in the far more culturally sensitive era. To his surprise, Kimmel absolutely does think it would do well.
"I think not only would it be possible, I think it would be more popular than it ever was," he said. "Especially in this world because there's a certain portion of society that's outraged by the outrage and I think that they would probably find it to be exhilarating."
Does that mean he might consider a return to the show that put him on the pop culture map?