| JACKWHITE | "Lazaretto" rock singer who headlined at the 2015 Coachella Festival: 2 wds. |
| THEWEEKND | "Earned It" R&B singer who headlined at the 2018 Coachella Festival: 2 wds. |
| LADY | With 39-Across "Born This Way" pop singer who headlined at the 2017 Coachella Festival |
| DIANAROSS | R&B singer who headlined the Essence Festival in New Orleans on June 30: 2 wds. |
| CALVIN | With 33-Across EDM DJ who headlined at the 2016 Coachella Festival |
| DUALIPA | With seven Brit Awards and three Grammys, who headlined at Glastonbury 2024? (3,4) |
| PALMEDOR | Big prize at the Cannes Film Festival: 2 wds. |
| CAROLCHANNING | Singer/actress who headlined the original production of "Hello, Dolly!" in 1964: 2 wds. |
| FANNYBRICE | Comic actress who headlined the Ziegfeld Follies in the early 20th century: 2 wds. |
| WEEKND | The ___ , Canadian R&B artist who headlined the halftime show at the Super Bowl in 2021 (6) |
| JIMIHENDRIX | US singer-songwriter and guitarist who headlined the iconic 1969 Woodstock Festival (4,7) |
| PEARLBAILEY | Singer/actress who headlined versions of "Hello, Dolly!" in 1967 and 1975: 2 wds. |
| HENDRIX | Jimi ---, US singer-songwriter and guitarist who headlined the iconic 1969 Woodstock Festival (7) |
| ANNEENRIGHT | Author of "The Green Road," the Novel of the Year at the 2015 Irish Book Awards: 2 wds. |
| CECILYSTRONG | Schmigadoon! comedian who was the featured entertainer at the 2015 White House Correspondents' Dinner: 2 wds. |
| RITCHIEVALENS | Rock singer who was the subject of the 1987 biopic "La Bamba": 2 wds. |
| JAMESBROWN | Rock singer who was the subject of the 2014 biopic "Get On Up": 2 wds. |
| ADAM | Singer Levine of Maroon 5 who headlined the Super Bowl LIII halftime show |
| NEIL | ___ Young, Canadian singer-songwriter who headlined Glastonbury Festival in 2025 (4) |
| OUTDOORCONCERTS | Main attractions at many summertime festivals: 2 wds. |
