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Hollywood Squares (2025)

Season 2 • Episode 8 • This Always Happens When RuPaul’s Around

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Hollywood Squares Season 2, Episode 8: This Always Happens When RuPaul’s Around

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Episodes

22 episodes
1

Santa's Got a Little Game

2

Hand This Man a Candy Cane

3

I Will Not Be Ignored, Glenn!

4

Between a Cardigan Sandwich

5

This Is the Best Show on TV

6

I'm Terrified of Triumph

7

Expect the Unexpected

8

This Always Happens When RuPaul’s Around

9

The Legacy Show

10

I Didn’t Know You Were That Flexible

11

Thicker Than a 1st Grade Pencil

12

I Have a Lot of Exes Watching Right Now

13

A Scream Reunion

14

I’m Nasty, But I Ain’t No Hero

15

This Isn’t Survivor

16

There’s That Cruella Energy

17

Please Don't Let It Be a Hawk

18

90s Fine Baby

19

We Have a Lot of SNL Funny in Here Tonight

20

Be Careful What You Ask for Howie

Celebrities Whitney Cummings, Mark Duplass, Ana Gasteyer, Tiffany Haddish, Triumph the Insult Comic Dog, Leslie Jones, Thomas Lennon, Howie Mandel and Ross Mathews.
21

The Wizard of Hollywood Squares

Celebrities Michelle Buteau, Kat Dennings, Tiffany Haddish, Pete Holmes, Thomas Lennon, Bobby Moynihan, Law Roach and Meghan Trainor.
22

Snooze We Can't Lose

Celebrities Tom Bergeron, Neal Brennan, Whitney Cummings, Ariana DeBose, Mark Duplass, Arsenio Hall, Tiffany Haddish and Ms. Pat.