Many of the sketches revolve around someone making an embarrassing mistake in a social or professional setting, then refusing to admit to it and instead stubbornly attempting to convince everyone that they are right and the people around them are wrong.

[4][5] The series is executive produced by Robinson and Kanin; Lonely Island members Andy Samberg, Akiva Schaffer and Jorma Taccone; and Alex Bach and Daniel Powell of Irony Point.

Guest stars across all three seasons include Sam Richardson, Patti Harrison, Conner O'Malley and Tim Heidecker alongside Samberg, Fred Armisen, Vanessa Bayer, Beck Bennett, Kate Berlant, Julia Butters, Ayo Edebiri, Will Forte, Paul Walter Hauser, Bob Odenkirk, Cecily Strong, Jason Schwartzman, Brandon Wardell, Fred Willard and Steven Yeun.

The website's critical consensus reads, "A gloriously absurd journey into the mind of Tim Robinson, I Think You Should Leave's bazaar of surreal skits breathes new life into the world of TV sketch-comedy.

The website's critical consensus reads, "A triumph of sketch comedy, I Think You Should Leave's sophomore season dives deeper into Tim Robinson and Zach Kanin's strange minds with manically delightful results.

Guests performers included Sam Richardson, Seth Meyers, Lionel Boyce, Patti Harrison, and Paul Rudd.