| Sketch | Career Day |
| Chance the Rapper | ... | Scott |
| Beck Bennett | ... | Bill |
| Aidy Bryant | ... | Mrs. Sellers |
| Pete Davidson | ... | Matthew Sellers |
| Mikey Day | ... | Robbie |
| Andrew Dismukes | ... | student |
| Luke Null | ... | student |
| Cecily Strong | ... | Mrs. Tylerson |
| Kenan Thompson | ... | Gary |
| Melissa Villaseñor | ... | student |
| Steven Castillo | ... | student |
| Sudi Green | ... | student |