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- Season 5 overviewJun 2-Aug 27, 202035 episodesSeason 5 episodes173. Chris Christie; Gregory Porter Aug 27, 2020
- Former Gov. Chris Christie (R-N.J.); Gregory Porter performs.
- 172. Nancy Pelosi; Lucinda Williams Aug 26, 2020
- Speaker of the House Nancy Pelosi; Lucinda Williams performs.
- 171. Trey Gowdy; Keanu Reeves; Alex Winter Aug 25, 2020
- Former Congressman Trey Gowdy (R-S.C.); actors Keanu Reeves and Alex Winter.
- Podcast hosts Jon Favreau, Jon Lovett and Tommy Vietor; Tim McGraw performs; actress Laura Benanti.
- 169. Hillary Rodham Clinton; The Killers Aug 20, 2020
- Former Secretary of State Hillary Rodham Clinton; The Killers perform.
- 168. Bernie Sanders; Nathaniel Rateliff Aug 19, 2020
- Sen. Bernie Sanders (D-Vt.); Jon Batiste and Nathaniel Rateliff perform.
- 167. Elizabeth Warren; Regina Spektor Aug 18, 2020
- Sen. Elizabeth Warren (D-Mass.); Regina Spektor performs.
- 166. Susan Rice; Sheryl Crow Aug 17, 2020
- Former National Security Advisor Susan Rice; Sheryl Crow performs.
- 165. John Heilemann; Mark McKinnon; Alex Wagner Aug 13, 2020
- Journalists John Heilemann and Alex Wagner; political adviser Mark McKinnon.
- 164. Jason Sudeikis; April Ryan Aug 12, 2020
- Actor Jason Sudeikis; journalist April Ryan.
- 163. Laura Linney Aug 11, 2020
- Actress Laura Linney.
- 162. Jon LaPook; Maroon 5 Aug 10, 2020
- Dr. Jon LaPook; Maroon 5 performs.
- 161. Ava DuVernay; Kristen Bell; Ben Folds Jul 23, 2020
- Filmmaker Ava DuVernay; actress Kristen Bell; Ben Folds performs.
- 160. Mary Trump; Kristen Bell Jul 22, 2020
- Author Mary Trump; actress Kristen Bell.
- 159. Greta Thunberg; Keegan-Michael Key Jul 21, 2020
- Activist Greta Thunberg; actor Keegan-Michael Key.
- 158. Andy Cohen; Phoebe Bridgers Jul 20, 2020
- TV host Andy Cohen; Phoebe Bridgers performs.
- 157. W. Kamau Bell; The Chicks Jul 16, 2020
- Comic W. Kamau Bell; The Chicks talk and perform.
- 156. Ricky Gervais; Noah Cyrus; Billy Ray Cyrus Jul 15, 2020
- Comic Ricky Gervais; Noah Cyrus and Billy Ray Cyrus perform.
- 155. Tom Hanks; Noah Cyrus; Billy Ray Cyrus Jul 14, 2020
- Actor Tom Hanks; Noah Cyrus and Billy Ray Cyrus perform.
- 154. Norah O'Donnell; IDK Jul 13, 2020
- Journalist Norah O'Donnell; IDK performs.
- 153. Ibram X. Kendi; Patton Oswalt Jun 25, 2020
- Author Ibram X. Kendi; comic Patton Oswalt.
- 152. Jon Stewart Jun 24, 2020
- Comic Jon Stewart.
- 151. John Bolton Jun 23, 2020
- John Bolton, former national security adviser.
- 150. James Corden; Laura Benanti; Bright Eyes Jun 22, 2020
- Talk show host James Corden; actress Laura Benanti; Bright Eyes perform.
- 149. Sherrilyn Ifill; Mike Birbiglia Jun 18, 2020
- Sherrilyn Ifill, President of the NAACP Legal Defense Fund; comic Mike Birbiglia.
- 148. Kamala Harris; Milky Chance; Jack Johnson Jun 17, 2020
- Sen. Kamala Harris (D-Calif.); Milky Chance and Jack Johnson perform.
- 147. Hasan Minhaj; Jason Isbell and the 400 Unit Jun 16, 2020
- TV personality Hasan Minhaj; Jason Isbell and the 400 Unit perform.
- 146. John Dickerson; Black Pumas Jun 15, 2020
- Journalist John Dickerson; Black Pumas perform.
- 145. Wesley Lowery; Judd Apatow Jun 11, 2020
- Journalist Wesley Lowery; filmmaker Judd Apatow.
- 144. Stacey Abrams; Megan Rapinoe; The Flaming Lips Jun 10, 2020
- Fair Fight Action founder Stacey Abrams; professional soccer player Megan Rapinoe; The Flaming Lips.