19x1 - Charles Barkley, The Chicks

September 21, 2020

Jimmy welcomes former professional basketball player Charles Barkley plus an interview with and musical performance by The Chicks.

19x3 - Riz Ahmed, Tim McGraw

September 23, 2020

Actor Riz Ahmed ("Mogul Mowgli" and "The Long Goodbye"); Tim McGraw (album, "Here on Earth") talks and performs.

19x12 - Armie Hammer/Marlon Wayans/Jaden Smith

October 6, 2020

Actor Armie Hammer (Rebecca (2020)); actor Marlon Wayans (On the Rocks (2020)); Jaden Smith performs;

19x27 - David Letterman/Gillian Jacobs/Gracie Abrams

October 28, 2020

TV host David Letterman ("My Next Guest Needs No Introduction with David Letterman"); actress Gillian Jacobs ("Come Play"); Gracie Abrams performs.

19x43 - Natalie Portman, Russell Dickerson

November 30, 2020

Actress Natalie Portman (book, "Natalie Portman's Fables"); "Who Wants to Be a Millionaire" celebrity winner Russell Dickerson performs;

19x58 - Tessa Thompson/Paul Bettany/Steve Earle

January 7, 2021

Tessa Thompson and Paul Bettany guest. Steve Earle performs.

19x65 - John Oliver/Charles P. Pierce/Ashley McBryde

January 20, 2021