Season 5 (2021)

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Rosie O'Donnell vs Nate Berkus and Michael Kosta vs Roy Wood Jr.
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May 26, 2021 • 45m

Featuring Rosie O'Donnell, Nate Berkus, Michael Kosta and Roy Wood Jr.

Rachel Dratch vs Chris Redd Tonight and Dr. Oz vs Daphne Oz"
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June 2, 2021 • 45m

Michael Strahan returns as host of "The $100,000 Pyramid" and he's bringing the hottest names in film, TV, sports, entertainment a...Read more

Alex Moffat vs Michelle Collins and Dominique Jackson vs Indya Moore
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June 16, 2021 • 45m

Featuring "Saturday Night Live" star Alex Moffat and comedian and radio host Michelle Collins followed by stars of FX's "Pose" Dom...Read more

Ali Wentworth vs. Sara Haines and Kal Penn vs. Michelle Buteau
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June 23, 2021 • 45m

Ali Wentworth vs. Sara Haines; and Kal Penn vs. Michelle Buteau.

Lorraine Bracco Vs Ralph Macchio And Rosie O'Donnell Vs Paige Davis
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June 30, 2021 • 45m

This week, Lorraine Bracco faces off against Ralph Macchio followed by actress and comedian Rosie O'Donnell and Paige Davis.

Joe Gatto vs Sal Vulcano and Desi Lydic vs Nikel Welch
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July 7, 2021 • 45m

Joe Gatto faces off against Sal Vulcano followed by comedian Desi Lydic and interior designer Mikel.

Bridget Everett Vs Dulce Sloan And Kathy Najimy Vs Mario Cantone
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July 21, 2021 • 45m

Bridget Everett Vs Dulce Sloan And Kathy Najimy Vs Mario Cantone

Ana Gasteyer Vs Rachel Dratch And Joe Gatto Vs James Murray
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July 28, 2021 • 45m

This week's celebrity guests are "Saturday Night Live" alums Ana Gasteyer and Rachel Dratch followed by "Impractical Jokers" Joe G...Read more

Ryan Eggold vs Elizabeth Marvel and Joe Tessitore vs Tiki Barber
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August 11, 2021 • 45m

Episode 9 of Season 5 premiered on August 11, 2021

Ginger Zee vs Dascha Polanco and Dorinda Medley vs Sonjia Morgan
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August 18, 2021 • 45m

Ginger Zee faces off against actress Dascha Polanco followed by Dorinda Medley and Sonja Morgan.

Ana Gasteyer vs Luke Kirby and Ashanti vs Clay Aiken
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August 25, 2021 • 45m

This week on "The $100,000 Pyramid," actress and comedian Ana Gasteyer faces off against actor Luke Kirby followed by actress and ...Read more

Kal Penn vs Kathy Najimy and Neil deGrasse Tyson vs Gilbert Gottfried
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September 1, 2021 • 45m

Episode 12 of Season 5 premiered on September 1, 2021

Mario Cantone Vs Laura Benanti And Joe Tessitore Vs Bridget Everett
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September 15, 2021 • 45m

Celebrity guests are actor and comedian Mario Cantone and actress Laura Benanti followed by Joe Tessitore (ABC's "Holey Moley") an...Read more