Hollywood Squares involves two contestants who play tic-tac-toe to win money and prizes. The "board" for the game is a vertical stack of open-faced cubes, each occupied by a celebrity seated at a desk and facing the contestants. The celebrities are asked questions and the contestants judge the legitimacy of their answers to win the game.
Celebrity guests Ariana DeBose, Ron Funches, Tiffany Haddish, Pete Holmes, Jo Koy, Boston Rob Mariano, Niecy Nash‑Betts and Ms. Pat.
E1
Celebrity contestants Anthony Anderson, Glenn Close, Pete Holmes, Whitney Cummings, Lil Rel Howery, Triumph the Insult Comic Dog, Leslie Jones and Ross Mathews.
E2
Celebrity contestants Whitney Cummings, Kat Dennings, Fortune Feimster, Pete Holmes, Tiffany Haddish, Padma Lakshmi, Joel McHale and RuPaul.
E3
Celebrity contestants Whitney Cummings, Ariana Debose, Fortune Feimster, Tiffany Haddish, Arsenio Hall, Lil Rel Howery, Jo Koy and Ms. Pat.
E4
Celebrity contestants Anthony Anderson, Glenn Close, Whitney Cummings, Zarna Garg, Pete Holmes, Triumph the Insult Comic Dog, Leslie Jones and Jay Mohr.
E5
Celebrity guests Tichina Arnold, Ana Gasteyer, Lil Rel Howery, Thomas Lennon, Tim Meadows, Julie Chen Moonves, Jason Ritter and Kristen Schaal.
E6
Celebrity guests Whitney Cummings, Zarna Garg, Tiffany Haddish, Pete Holmes, Padma Lakshmi, Thomas Lennon, Joel McHale and RuPaul.
E7
Celebrity guests Tom Bergeron, Whitney Cummings, Tiffany Haddish, Arsenio Hall, Howie Mandel, Thomas Lennon, Leslie Jones and Triumph the Insult Comic Dog.
E8
Celebrity guests Whitney Cummings, Fortune Feimster, Zarna Garg, Tiffany Haddish, Robby Hoffman, Padma Lakshmi, Thomas Lennon, Bill Maher, Joel McHale and Triumph the Insult Comic Dog.
E9
Celebrity guests Michelle Buteau, Ana Gasteyer, Triumph the Insult Comic Dog, Janelle James, Method Man, Bobby Moynihan, Tig Notaro and Paul Scheer.
E10
Celebrity guests Ariana DeBose, Ron Funches, Gabriel "Fluffy" Iglesias, Tiffany Haddish, Pete Holmes, Niecy Nash‑Betts, Ms. Pat and Paul Scheer.
E11
Celebrity guests David Arquette, Whitney Cummings, Mark Duplass, Tiffany Haddish, Pete Holmes, Triumph the Insult Comic Dog, Leslie Jones and Thomas Lennon.
E12
Celebrity guests Whitney Cummings, Ariana Debose, Fortune Feimster, Ryan Fitzpatrick, Tiffany Haddish, Lil Rel Howery, Gabriel Iglesias and Jo Koy.
Celebrity guests Ariana DeBose, Ron Funches, Tiffany Haddish, Pete Holmes, Jo Koy, Boston Rob Mariano, Niecy Nash‑Betts and Ms. Pat.
Celebrity contestants Neal Brennan, Glenn Close, Whitney Cummings, Robby Hoffman, Lil Rel Howery, Triumph the Insult Comic Dog, Leslie Jones and Howie Mandel.
