Hollywood Squares (2025) S2 E8 | This Always Happens When RuPaul's Around

You must connect to your TV Provider to watch this video.

This Always Happens When RuPaul's Around

Help

S2 E8 21min TV-PG D, L

Celebrity Squares: Whitney Cummings, Zarna Garg, Tiffany Haddish, Pete Holmes, Padma Lakshmi, Thomas Lennon, Joel McHale and RuPaul. Air Date: Jan 21, 2026

NEW EPISODES WEDNESDAYS

Full Episodes

S2 E15 03/11/26

This Isn't Survivor

S2 E14 02/22/26

I'm Nasty, But I Ain't No Hero

S2 E13 02/22/26

A Scream Reunion

S2 E12 02/04/26

I Have a Lot of Exes Watching Right Now

S2 E11 02/04/26

Thicker Than a 1st Grade Pencil

Hollywood Squares (2025) - I Didn't Know You Were That Flexible

S2 E10 01/28/26

I Didn't Know You Were That Flexible

Hollywood Squares (2025) - The Legacy Show

S2 E9 01/28/26

The Legacy Show

Hollywood Squares (2025) - This Always Happens When RuPaul's Around

S2 E8 01/21/26

This Always Happens When RuPaul's Around

Hollywood Squares (2025) - Expect the Unexpected

S2 E7 01/21/26

Expect the Unexpected

Hollywood Squares (2025) - I'm Terrified of Triumph

S2 E6 01/14/26

I'm Terrified of Triumph

Hollywood Squares (2025) - This Is the Best Show on TV

S2 E5 01/14/26

This Is the Best Show on TV

Hollywood Squares (2025) - Between a Cardigan Sandwich

S2 E4 01/07/26

Between a Cardigan Sandwich

Hollywood Squares (2025) S2 E8 | This Always Happens When RuPaul's Around

Full Episodes

Clips