Saturday Night Live - Season 0 Episode 153 : Digital Short: Andy and Pee-wee's Night Out 2024

Samberg has some shots with none other than Pee Wee Herman (Paul Reubens). After beating Anderson Cooper (who appears as himself) over the head with a chair, Samberg and Pee-Wee are caught by the police, to which they escape by hitting the officer with a chair. When they return to Samberg's apartment, they come to an intervention with Cooper (bandaged up from being hit in the face with a chair by Pee-Wee and Samberg), Samberg's friends (Fred Armisen, Kristen Wiig, and Kenan Thompson), and Pee Wee's Playhouse friends Chairry, Pterri, and Conky, who plead with Andy and Pee-Wee never to be friends again. Andy and Pee-Wee reluctantly agree, and everybody celebrates the breakup with more shots.