Hollywood Squares (2025)

This Always Happens When RuPaul’s Around

TV-14
S2 • E8    Jan 21, 2026
2.8
Celebrity squares include Whitney Cummings, Zarna Garg, Tiffany Haddish, Pete Holmes, Padma Lakshmi, Thomas Lennon, Joel McHale and RuPaul.

Where to Watch Hollywood Squares (2025) - S2 • E8

Cast of This Always Happens When RuPaul’s Around

  • Nate BurlesonSelf - Host
  • Drew BarrymoreSelf
  • Whitney CummingsSelf
  • Tiffany HaddishSelf
  • Thomas LennonSelf
  • Pete HolmesSelf
  • RuPaulSelf
  • Padma LakshmiSelf
  • Joel McHaleSelf
  • Zarna GargSelf

 

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