| Date | Grid | Clue | Author | Editor |
| Tue, Mar 15, 2022 | 21A | Rapper with the line "I'm not a businessman, I'm a business, man" | Michael Lieberman | Shortz |
| Tue, Oct 29, 2019 | 57D | Rapper whose name hints at the extremities of the answers to the five starred clues | Evan Mahnken | Shortz |
| Sun, Sep 10, 2017 | 7D | Rapper with the music streaming service Tidal | Brendan Emmett Quigley | Shortz |
| Tue, Aug 18, 2015 | 27D | Rapper born Shawn Corey Carter | Bill Thompson | Shortz |
| Wed, Feb 03, 2010 | 48A | Rapper with the #1 hit "Empire State of Mind" | Kristian House | Shortz |
| Tue, Sep 09, 2008 | 41D | Rap star who co-owns the New Jersey Nets | Patrick John Duggan | Shortz |
| Thu, Mar 16, 2006 | 1D | Rapper who co-founded Roc-a-Fella Records | Ben Tausig | Shortz |