| Person: | Characters | Episodes | |
| • Michael Hogan (4) | played | 5 Episodes | |
| • A.O. Scott | played | 3 Episodes | |
| • Sharon Profis | played | 3 Episodes | |
| • Scott Stein | played | 3 Episodes | |
| • Lucy Liu | played | 2 Episodes | |
| • Al Green (1) | played | 2 Episodes | |
| • Lily Tomlin | played | 2 Episodes | |
| • Julie Chen | played | 2 Episodes | |
| • Oprah Winfrey | played | 2 Episodes | |
| • Aisha Tyler | played | 2 Episodes | |
| • Barack Obama | played | 2 Episodes | |
| • Diane von Fürstenberg | played | 2 Episodes | |
| • Bill Cowher | played | 2 Episodes | |
| • Keegan-Michael Key | played | 2 Episodes | |
| • Benedict Cumberbatch | played | 2 Episodes | |
| • Jordan Peele | played | 2 Episodes | |
| • Douglas Brinkley | played | 2 Episodes | |
| • Taylor Swift | played | 2 Episodes | |
| • Eddie Redmayne | played | 2 Episodes | |
| • Bart Scott | played | 2 Episodes | |
| • Beth Behrs | played | 2 Episodes | |
| • Jason Silva | played | 2 Episodes | |
| • Brian Kelly (4) | played | 2 Episodes | |
| • David Gilboa | played | 2 Episodes | |
| • Neil Blumenthal | played | 2 Episodes | |
| • Lloyd Blankfein | played | 2 Episodes | |
| • Kara Walker | played | 2 Episodes | |
| • Martine Rothblatt | played | 2 Episodes | |
| • Jenna Lyons | played | 2 Episodes | |
| • Tony Schwartz | played | 2 Episodes | |
| • Natalie Zmuda | played | 2 Episodes |