| Show | Hip Hop Classics |
| Drake | ... | Jay-Z |
| Drake | ... | Lil Wayne |
| Vanessa Bayer | ... | Felicity |
| Taran Killam | ... | Eminem |
| Kate McKinnon | ... | student |
| Nasim Pedrad | ... | Jenna von Oÿ |
| Jay Pharoah | ... | 2 Chainz |
| Jay Pharoah | ... | Eddie |
| Kenan Thompson | ... | Carl |
| Kenan Thompson | ... | Rick Ross |
| Kenan Thompson | ... | Sway |
| Kenan Thompson | ... | Flavor Flav Voice |
| Beck Bennett | ... | Don Herbert /Mr. Wizard |
| Kyle Mooney | ... | Joey Lawrence |
| Noël Wells | ... | student |
| Brooks Wheelan | ... | Ben |
| Sasheer Zamata | ... | Cindy |
| Sasheer Zamata | ... | Rihanna |