Awards shows are nothing without their scamps. What would the 2000 VMAs have been without that guy from Rage Against the Machine climbing the set? Remember when Amy Poehler organized a wedding photo booth’s worth of props for the Comedy Supporting Actresses at the 2009 Emmys, and then the Comedy Actress pageant in 2011? These are the moments people will remember for years, not the two-page prepared speeches. (Lookin’ at you, Queen’s Gambit.) Conan O’Brien, who lost an Emmy to John Oliver early in the night, brought the fun once the burden of winning was off his shoulders.
First, Oliver thanked O’Brien for his decades of inspiring comedians. Thankfully, the camera cut to O’Brien for his reaction.
Then, O’Brien popped up when Frank Scherma, president of the Television Academy, stepped up to present the Governors Award to Debbie Allen. O’Brien cheered and cheered and demanded the whole room give a standing ovation. Many loved it, though some criticized the timing, as Allen was the first Black woman to receive the Governors Award. After an acknowledgement from Scherma, O’Brien saluted him and went back to his seat.
O’Brien’s final trolling moment of the night came when Stephen Colbert won Outstanding Variety Special (Live) for Stephen Colbert’s Election Night 2020: Democracy’s Last Stand: Building Back America Great Again Better 2020. Conan crashed the podium, sneaking in among the group of besuited fellas who actually belonged there. “Most of the people behind me really deserve this Emmy right now,” Colbert said after noticing O’Brien’s presence onstage. O’Brien may or may not have had his fly open at the time. Legend.