Video: Triumph Taunts Fallon About Nicole Kidman, Conan's Tonight Run

File under: #ThatAwkwardMoment.

On Thursday’s Tonight Show Starring Jimmy Fallon, former Conan O’Brien staple Triumph the Insult Comic Dog appeared alongside 30 Rock vet Jack McBrayer to promote their new Adult Swim series The Jack and Triumph Show (premiering Feb. 20). Triumph (as puppeteered by former Late Night with Conan O’Brien scribe Robert Smigel) continuously interrupted his co-star, which was funny… until it wasn’t.

After a bit that found the puppet lampooning Fallon’s missed opportunity with Nicole Kidman and the host’s right-hand man, Steve Higgins, he ventured into pretty uncomfortable territory, such as bringing up NBC’s poor treatment of one-time Tonight Show host O’Brien. He even got in a dig at Roots bandleader Questlove when comparing his musicianship to Max Weinberg.

Hit the PLAY button above, and we dare you not to cringe.