I Think You Should Leave Season 2 Release Date, Cast And Plot
Eleanor Gray
Published Mar 07, 2026
We know we'll see the return of creators Robinson and Kanin, who appear in nearly every sketch in the first season (although Kanin's supporting roles are uncredited). The creators have a combined 12 years of experience as writers for the longest-running sketch show of all time, "Saturday Night Live." And with access to a large cache of comedic actors, it's likely we'll see the return of friendly "SNL" faces like Vanessa Bayer, Cecily Strong, and Will Forte.
To add to the comedic clout, the creators mentioned Season 2 of "I Think You Should Leave" will once again involve The Lonely Island comedy group helmed by "SNL" alum and "Brooklyn 99" star Andy Samberg — who also appeared in Season 1.
Although jam-packed with his fellow alumni, Robinson also made sure to vary Season 1's cast. Sketches featured "Minari" star Steven Yeun, "Best of Show" star Fred Willard, Tim Heidecker of "Tim and Eric," Michelle Ortiz of "Gentefied," and Cuban character actor, Ruben Rabasa, among other familiar faces. Since sketches rely on the trusted delivery of their actors, it's likely we'll see the return of Robinson's friends in Season 2, as well.
"I Think You Should Leave With Tim Robinson" was named by Variety as one of the best shows to watch in 2019, and was in the company of other hit comedies like "Pen15," "Barry," "Fleabag," and Netflix's animated series, "Tuca & Bertie."