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Season 5

3 Sep. 2019
Jim Gaffigan/Ann Curry
Actor Jim Gaffigan (American Dreamer (2018)); journalist Ann Curry (Chasing the Cure (2019)).
 
4 Sep. 2019
Vice President Joe Biden/Pixies
Former Vice President and presidential candidate Joe Biden. Also: Pixies perform.
 
5 Sep. 2019
Mayor Pete Buttigieg/Graham Norton
South Bend, Indiana mayor and presidential candidate Pete Buttigieg; Graham Norton (The Graham Norton Show (2007), novel "A Keeper").
 
9 Sep. 2019
Sec. Condoleezza Rice/Bill Skarsgård/Banks
Former Secretary of State Condoleezza Rice (book "To Build a Better World: Choices to End the Cold War and Create a Global Commonwealth"); actor Bill Skarsgård (It Chapter Two (2019)). Also: Banks performs.
 
10 Sep. 2019
Ansel Elgort/Jodi Kantor and Megan Twohey
Actor Ansel Elgort (The Goldfinch (2019)); journalists Jodi Kantor and Megan Twohey (book "She Said: Breaking the Sexual Harassment Story That Helped Ignite a Movement").
 
11 Sep. 2019
James McAvoy/Stephen King/Vampire Weekend
Actor James McAvoy (It Chapter Two (2019)); author Stephen King (novel "The Institute"). Also: Vampire Weekend performs.
 
12 Sep. 2019
Jake Tapper/Jon Lovett
In a live broadcast after the third Democratic presidential debate, Stephen welcomes journalist Jake Tapper (The Lead with Jake Tapper (2013)) and podcast host Jon Lovett ("Lovett or Leave It").
 
16 Sep. 2019
Tom Hiddleston/Marie Osmond
Actor Tom Hiddleston (Avengers: Endgame (2019)); talk show hostess Marie Osmond (The Talk (2010));
 
17 Sep. 2019
Elizabeth Warren/Barry Williams/Maureen McCormick/Christopher Knight/Eve Plumb/Mike Lookinland/Susan Olsen
Sen. Elizabeth Warren (D-Mass), 2020 Democratic presidential candidate; actors Barry Williams, Maureen McCormick, Christopher Knight, Eve Plumb, Mike Lookinland, and Susan Olsen (The Brady Bunch (1969));
 
18 Sep. 2019
Billy Crystal/Thomas Rhett
Actor Billy Crystal; Thomas Rhett performs;
 
19 Sep. 2019
Taraji P. Henson/Aasif Mandvi/Kevin Camia
Actress Taraji P. Henson (Empire (2015)); actor Aasif Mandvi (Human Capital (2019)); comic Kevin Camia;
 

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