Season 5

01 Rosie O'Donnell vs Nate Berkus and Michael Kosta vs Roy Wood Jr. Episode 126th May 2021 Featuring Rosie O'Donnell, Nate Berkus, Michael Kosta and Roy Wood Jr. 02 Rachel Dratch vs Chris Redd Tonight and Dr. Oz vs Daphne Oz" Episode 22nd June 2021 Michael Strahan returns as host of "The $100,000 Pyramid" and he's bringing the hottest names in film, TV, sports, entertainment and comedy with him to ABC Wednesday nights. This week, "Saturday Night Live" stars Rachel Dratch and Chris Redd compete for the winner's circle, and Dr. Mehmet Oz squares off against his daughter Daphne Oz. 03 Alex Moffat vs Michelle Collins and Dominique Jackson vs Indya Moore Episode 316th June 2021 Featuring "Saturday Night Live" star Alex Moffat and comedian and radio host Michelle Collins followed by stars of FX's "Pose" Dominique Jackson and Indya Moore. 04 Ali Wentworth vs. Sara Haines and Kal Penn vs. Michelle Buteau Episode 423rd June 2021 Ali Wentworth vs. Sara Haines; and Kal Penn vs. Michelle Buteau. 05 Lorraine Bracco Vs Ralph Macchio And Rosie O'Donnell Vs Paige Davis Episode 530th June 2021 This week, Lorraine Bracco faces off against Ralph Macchio followed by actress and comedian Rosie O'Donnell and Paige Davis. 06 Joe Gatto vs Sal Vulcano and Desi Lydic vs Nikel Welch Episode 67th July 2021 Joe Gatto faces off against Sal Vulcano followed by comedian Desi Lydic and interior designer Mikel. 07 Bridget Everett Vs Dulce Sloan And Kathy Najimy Vs Mario Cantone Episode 721st July 2021 Bridget Everett Vs Dulce Sloan And Kathy Najimy Vs Mario Cantone 08 Ana Gasteyer Vs Rachel Dratch And Joe Gatto Vs James Murray Episode 828th July 2021 This week's celebrity guests are "Saturday Night Live" alums Ana Gasteyer and Rachel Dratch followed by "Impractical Jokers" Joe Gatto and James Murray. 09 Ryan Eggold vs Elizabeth Marvel and Joe Tessitore vs Tiki Barber Episode 911th August 2021 10 Ginger Zee vs Dascha Polanco and Dorinda Medley vs Sonjia Morgan Episode 1018th August 2021 Ginger Zee faces off against actress Dascha Polanco followed by Dorinda Medley and Sonja Morgan. 11 Ana Gasteyer vs Luke Kirby and Ashanti vs Clay Aiken Episode 1125th August 2021 This week on "The $100,000 Pyramid," actress and comedian Ana Gasteyer faces off against actor Luke Kirby followed by actress and singer Ashanti and singer Clay Aiken. 12 Kal Penn vs Kathy Najimy and Neil deGrasse Tyson vs Gilbert Gottfried Episode 121st September 2021 13 Mario Cantone Vs Laura Benanti And Joe Tessitore Vs Bridget Everett Episode 1315th September 2021 Celebrity guests are actor and comedian Mario Cantone and actress Laura Benanti followed by Joe Tessitore (ABC's "Holey Moley") and comedian Bridget Everett.