| Show | Will & Todd's Radical Experience |
| Quinta Brunson | ... | Harriet Tubman |
| Mikey Day | ... | Leonardo da Vinci |
| Andrew Dismukes | ... | Todd |
| Chloe Fineman | ... | Queen Elizabeth I |
| Marcello Hernández | ... | Will |
| Kenan Thompson | ... | Frederick Douglass |
| Devon Walker | ... | guy |
| Emil Wakim | ... | Julius Caesar |
| Steve Higgins | ... | announcer Voice |
⁕Marcello Hernández almost refers to Mikey Day as "Leo DiCaprio" and then quickly corrects himself.