| Date | Grid | Clue | Author | Editor |
|---|---|---|---|---|
| Sun, Sep 24, 2023 | 13A | Chill dude | Joel Fagliano and Christina Iverson | Shortz |
| Thu, May 02, 2013 | 55A | Hipster | Josh Knapp | Shortz |
| Mon, Feb 01, 2010 | 22D | Beat Generation persona | Scott Atkinson | Shortz |
| Tue, Jul 31, 2007 | 40A | *Hipster | Allan E. Parrish | Shortz |
| Tue, Nov 04, 2003 | 29A | Hip person | Elizabeth C. Gorski | Shortz |
| Fri, Jun 07, 2002 | 38D | Daddy-o | Manny Nosowsky | Shortz |