Will the two make eyes roll by cracking tired jokes about Leno coming back to take Fallon’s job? You betcha. Will it be awkward because of the small sliver of time that has passed and the notion that Leno left while still coveting the job? Absolutely, but even if that wasn’t the case, it would still be a little weird to see Leno stop by his old network and time slot since former hosts rarely return to their old shows. Of the hosts who have returned the most memorable visits include David Letterman’s surprise walk-on during an episode of Late Night with Conan O’Brien to make sure he and Joan Collins were copacetic and Conan’s post-Tonight Show exit appearance on Late Night with Jimmy Fallon to retrieve an old friend.
Interestingly, the most famous late night homecoming is probably the one that didn’t happen. Johnny Carson never went back to visit Leno’s Tonight Show. Instead, Carson made his only post-Tonight Show late night appearance on CBS when he stopped by David Letterman’s Late Show, a move that feels like a subtle repudiation of Leno and the methods that were used to help him cut in line to get the Tonight Show job in the first place. Just a great old school f-you move by Carson.
After more than 30 years in late night, Letterman is now a Carson-esque giant in the eyes of present day hosts like Jimmy Kimmel and Jon Stewart.
For Kimmel especially, Letterman’s appearance on his show in 2012 seemed like the realization of a childhood dream. Kimmel worshiped Letterman as a teenager, rocking a Late Night with David Letterman jacket and driving around with a L8Nite vanity license plate. Kimmel also framed a letter from Letterman that he received when Letterman declined an invitation to be on the first episode of Jimmy Kimmel Live. You know you’re a comedy nerd if all of these things sound amazing instead of weird or sad.
While Letterman didn’t appear on Kimmel’s first episode, he did take the time to appear on the last episode of Jon Stewart’s brief show in the 90s with a cigar in his mouth, a smile on his face, and a tone that was nearly consolatory. Remember, Letterman’s first show was a morning show that died a quick death too.
In 1998, Stewart found himself in the guest chair as another show neared its conclusion under much happier circumstances when he stopped by Craig Kilborn’s second-to-last episode of The Daily Show. While it wasn’t as awkward as Stewart’s earlier appearance on The Daily Show, there still isn’t a lot of warmth between the two men.