In the Season 5 premiere of Brooklyn Nine-Nine, Jake (Andy Samberg) and Rosa (Stephanie Beatriz) are in prison. When Holt and Terry visit Rosa she asks them for outrageous favors while Jake bonds with his cellmate Caleb — and is forced to join a prison gang led by Romero (guest star Lou Diamond Phillips).
Caleb is portrayed by Tim Meadows. He’s known for his roles on The Goldbergs (Mr. Glascott), Son of Zorn (Craig), Suburgatory (Edmond), Mr. Box Office (Principal Theodore Martin), and for his years on Saturday Night Live (1991-2000), among others. Meadows is also recognized for his roles in the films Mean Girls (Mr. Duvall), The Ladies Man (Leon Phelps), and Walk Hard: The Dewey Cox Story (Sam). Brooklyn Nine-Nine airs Tuesdays at 9:30pm ON FOX, after The Mick.