After 13 years, Conan O’ Brien is reunited with Letterman when the former visited the Late Show, and it all ends up in them discussing Jay Leno. If you’re not familiar with the scenario, both men have the distinction of losing The Tonight Show to Leno, Letterman in the early ’90s and Conan after he was ousted in 2010 because of poor ratings.
It was an awkward, silent moment when Conan sat in so Letterman didn’t waste any time by putting the ice breaker saying, “The longer we sit here, the more uncomfortable it’ll make Jay.” To which Conan responded, “You know Jay’s watching right now: He’s getting a live feed in a satellite truck right now.”
Watch these two late-night talk show hosts poke fun at Leno in these hilarious clips: