| 100% | JUSTINBIEBER | 12 | Pop singer who released the #1 album "My World 2.0" in 2010, at age 16: 2 wds. |
| 71% | BRITNEYSPEARS | 13 | Pop singer who released the #1 album "… Baby One More Time" in 1999, at age 17: 2 wds. |
| 59% | STEVIEWONDER | 12 | R&B singer who released the #1 album "Recorded Live: The 12 Year Old Genius" in 1963, at age 13: 2 wds. |
| 54% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 47% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 46% | BRETTFAVRE | 10 | Quarterback who was a starter with the Minnesota Vikings in 2010 at age 41: 2 wds. |
| 46% | NEILYOUNG | 9 | Canadian-born singer who released "Rockin' in the Free World" in 1989: 2 wds. |
| 44% | LADYGAGA | 8 | 15-Across, 9-Down, and 22-Down singer who released the studio album "Mayhem" in 2025 (2 wds.) |
| 43% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 41% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 41% | JUSTINBIEBER | 12 | Musician whose first album titled "My World 2.0" was declared triple platinum in 2010 when he was just 16 years old: 2 wds. |
| 41% | BILLYPRESTON | 12 | Singer who sang with Nat King Cole on a TV show at 11 and released his first album at 16: 2 wds. |
| 41% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 40% | ASHLEIGHBARTY | 13 | #1 tennis player who retired in 2022 at the age of 25: 2 wds. |
| 40% | EDSHEERAN | 9 | "Shape of You" singer who won two awards, including Best Pop Vocal Album, at the 2018 Grammy Awards (2 wds.) |
| 40% | COREYHART | 9 | Canadian-born singer who released "Sunglasses at Night" in 1984: 2 wds. |
| 40% | FIONAAPPLE | 10 | 18-Across, 25-Across, and 38-Across singer who released her fifth studio album "Fetch the Boltcutters" in 2020 (2 wds.) |
| 40% | JANELLEMONAE | 12 | Singer who featured the android character Cindi Mayweather on her 2010 "The ArchAndroid" concept album: 2 wds. |
| 40% | DICKSARGENT | 11 | "Bewitched" actor who came out of the closet in 1991 at age 61: 2 wds. |
| 39% | TAYLORSWIFT | 11 | "Cardigan" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 39% | LADYGAGA | 8 | "Shallow" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 39% | GEORGETAKEI | 11 | "Star Trek" actor who came out of the closet in 2005 at age 68: 2 wds. |
| 39% | MATTHASSELBECK | 14 | Quarterback who was a starter with the Indianapolis Colts in 2015 at age 40: 2 wds. |
| 39% | JUSTINBIEBER | 12 | "Yummy" singer with the 2021 #1 song at 16-Across and the #1 album at 44-Across: 2 wds. |
| 39% | DOUGFLUTIE | 10 | Quarterback who was a starter with the San Diego Chargers in 2005 at age 42: 2 wds. |
| 39% | JORDANROMERO | 12 | Mountaineer who climbed Mount Everest at the age of 13 and later became the youngest climber in the world to complete the Seven Summits: 2 wds. |
| 39% | VALERIEHARPER | 13 | Emmy-winning "Rhoda" star who competed on "Dancing With the Stars" in 2013 at age 74: 2 wds. |
| 38% | JENNIFERLOPEZ | 13 | "If You Had My Love" singer who received the Billboard Women in Music Icon Award in 2020: 2 wds. |
| 38% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 38% | HOLLANDTAYLOR | 13 | "Two and a Half Men" actress who came out of the closet in 2015 at age 72: 2 wds. |