After Jay Leno Was Mentioned On The Masked Singer, Andy Richter Told Us About An Awkward Encounter In A Diner With Conan's Late-Night Rival

The Masked Singer is a guessing game, and celebrities rivalries can make for risky choices. For example, when the first round of Group B performances hit Fox's Fall TV lineup, I couldn't help but gasp when panelist Rita Ora wrongfully thought Andy Richter was Jay Leno, former Tonight Show host and rival of Late Night's Richter and Conan O'Brien. CinemaBlend learned directly from the former sidekick how he felt about that guess, along with a wild story about him running into Leno at a diner.

I was lucky enough to speak to Richter after the The Masked Singer Season 12 episode where he was unmasked as Dust Bunny, and asked for his thoughts about being guessed as the comic who played an antagonistic role in the late night debacle that allegedly still bothers his former co-host Conan O'Brien years later. Richter offered his thoughts on the comparison and shared about the time he accidentally ran into Leno a couple of years ago:

I think it was sort of just when it was based on the clues, which I can't blame her, and honestly…it didn't bother me, you know? Yeah, it's a complicated history, but I actually sat down at the diner counter a couple of years ago and it was a busy Sunday morning at a very popular restaurant in Burbank. And there was one seat left at the counter, and I sat down, and I turned to my right and there was Jay Leno eating breakfast. So it was like, ‘Well, I guess we're gonna chat now.’ And it was fine, you know, I mean, all of that showbiz rivalry is like high school rivalry. Once you're past it, it's not that important.

It's good to hear he can put it behind him now, especially given how many people are still mad about the cancellation of The Tonight Show With Conan O'Brien, which inspired him to lift anchor and strike a deal with TBS. O'Brien and Andy Richter were bumped out of their prestigious roles when Leno decided to walk back on his retirement, forcing O'Brien out. Leno eventually retired again, paving the way for current host Jimmy Fallon to take over.

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Jimmy Fallon on The Tonight Show with Jimmy Fallon

(Image credit: Todd Owyoung/NBC)

I get where he's coming from.

Conan O'Brien and his wonderful on-air sidekick Richter eventually found their way back to late-night television via Conan, but the host largely avoided talking about it for years. On the other hand, Richter had given several interviews over the years, being critical of both NBC and Jay Leno for deciding to pull them from the coveted late-night program. As he said, it's complicated.

I'm sure that had to play into the awkwardness of their diner meeting, which I'm impressed he committed to. Had I been in the same situation with anyone in a similar position, I would've just walked out the door without a word!

Andy Richter's performance on The Masked Singer Season 12 was impressive, but unfortunately, Group B is loaded with talent. His performance of "Sweet Caroline" by Neil Diamond was about as good as anyone could do, and honestly, I think he would've survived at least a week had he been in Group A. The good news is that his early elimination prevented him from having to suit up as the Dust Bunny again, which he confirmed to CinemaBlend was a hot costume to be in.

With one contestant down, we'll have to continue to tune into The Masked Singer on Fox on Wednesdays at 8:00 p.m. ET to see who will win Group B.

Mick Joest
Content Producer

Mick Joest is a Content Producer for CinemaBlend with his hand in an eclectic mix of television goodness. Star Trek is his main jam, but he also regularly reports on happenings in the world of Star Trek, WWE, Doctor Who, 90 Day Fiancé, Quantum Leap, and Big Brother. He graduated from the University of Southern Indiana with a degree in Journalism and a minor in Radio and Television. He's great at hosting panels and appearing on podcasts if given the chance as well.