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- S5.E1 ∙ Jim Gaffigan/Ann Curry
- S5.E2 ∙ Vice President Joe Biden/Pixies
- S5.E3 ∙ Mayor Pete Buttigieg/Graham Norton
- S5.E4 ∙ Sec. Condoleezza Rice/Bill Skarsgård/Banks
- S5.E5 ∙ Ansel Elgort/Jodi Kantor and Megan Twohey
- S5.E6 ∙ James McAvoy/Stephen King/Vampire Weekend
- S5.E7 ∙ Jake Tapper/Jon Lovett
- S5.E8 ∙ Tom Hiddleston/Marie Osmond
- S5.E9 ∙ Senator Elizabeth Warren/The Brady Bunch
- S5.E10 ∙ Billy Crystal/Thomas Rhett
- S5.E11 ∙ Taraji P. Henson/Aasif Mandvi/Kevin Camia
- S5.E12 ∙ The Best of Season 4
- S5.E13 ∙ Paul McCartney
- S5.E14 ∙ Whoopi Goldberg/Ta-Nehisi Coates
- S5.E15 ∙ Renée Zellweger/Walton Goggins/Jacinda Ardern
- S5.E16 ∙ Sen. Bernie Sanders/Brittany Howard
- S5.E17 ∙ Patricia Heaton/Tegan and Sara
- S5.E18 ∙ Sec. Hillary Rodham Clinton and Chelsea Clinton/Wilco
- S5.E19 ∙ Rachel Maddow/Thom Yorke
- S5.E20 ∙ Rami Malek/Jill Soloway/Leah Bonnema
- S5.E21 ∙ Carrie Underwood/Kevin Smith and Jason Mewes
- S5.E22 ∙ Pete Alonso/Jon Hamm
- S5.E23 ∙ Neil deGrasse Tyson/Susan Rice
- S5.E24 ∙ Will Smith/Andrew Scott
- S5.E25 ∙ Jonathan Van Ness/Brett Gelman
- S5.E26 ∙ John Oliver and Amy Sedaris/Paul McCartney/Big Thief
- S5.E27 ∙ Julie Andrews/Jonathan Groff/Yungblud feat. Dan Reynolds
- S5.E28 ∙ John Lithgow/Camila Mendes
- S5.E29 ∙ Ronan Farrow/Andrea Savage
- S5.E30 ∙ Steve Carell/Toby Keith
- S5.E31 ∙ Eddie Murphy/Ree Drummond
- S5.E32 ∙ Queen Latifah/Radhika Jones
- S5.E33 ∙ Jennifer Aniston/Thomas Middleditch
- S5.E34 ∙ Norman Reedus/Cynthia Erivo/Miranda Lambert
- S5.E35 ∙ Speaker Nancy Pelosi
- S5.E36 ∙ Conan O'Brien/Curtis '50 Cent' Jackson/Rob Corddry
- S5.E37 ∙ Tim McGraw/Sen. Sherrod Brown
- S5.E38 ∙ Elizabeth Banks/Amy Klobuchar/King Princess
- S5.E39 ∙ Helen Mirren & Ian McKellen/Kids from MasterChef Junior
- S5.E40 ∙ John Dickerson/King Princess
- S5.E41 ∙ Liev Schreiber/Daniel Kaluuya/Cold War Kids
- S5.E42 ∙ Tim Robbins/Nicolle Wallace
- S5.E43 ∙ Mark Ruffalo/Andy Cohen/Thom Yorke
- S5.E44 ∙ David Harbour/Karen Olivo and Aaron Tveit/Moulin Rouge!
- S5.E45 ∙ Prime Minister Jacinda Ardern/Adam Driver/The 1975
- S5.E46 ∙ Helena Bonham Carter/Lady Antebellum/Lucy Lawless/Bret McKenzie
- S5.E47 ∙ Stephen Plays Rugby/John Heilemann and Alex Wagner
- S5.E48 ∙ New Lord of the Rings/Sen. Kamala Harris/Lady Antebellum
- S5.E49 ∙ New Zealand Outdoors/Daniel Craig/Lena Waithe
- S5.E50 ∙ Robert De Niro/J.J. Abrams