| 100% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 61% | BRITNEYSPEARS | 13 | Pop singer who released the #1 album "… Baby One More Time" in 1999, at age 17: 2 wds. |
| 56% | FETTYWAP | 8 | "Trap Queen" rapper who released a self-titled #1 album in 2015: 2 wds. |
| 56% | JUSTINBIEBER | 12 | Pop singer who released the #1 album "My World 2.0" in 2010, at age 16: 2 wds. |
| 55% | OSCARDELAHOYA | 13 | Famed boxer nicknamed "Golden Boy" who released a self-titled Latin Pop album in 2000 - receiving a grammy nomination!: 2 wds. |
| 53% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 50% | EDSHEERAN | 9 | "Shape of You" pop singer who had 13 songs on the Hot 100 during a week in 2017: 2 wds. |
| 48% | BILLIEEILISH | 12 | Singer who released "Birds of a Feather" in 2024: 2 wds. |
| 46% | STEVIEWONDER | 12 | R&B singer who released the #1 album "Recorded Live: The 12 Year Old Genius" in 1963, at age 13: 2 wds. |
| 46% | CHEAPTRICK | 10 | "The Flame" rock band that released a self-titled album in both 1977 and 1997: 2 wds. |
| 45% | CHRISSTAPLETON | 14 | "From a Room: Volume 1" singer who won the 2017 CMA Awards for Male Vocalist of the Year and Album of the Year (2 wds.) |
| 45% | FLEETWOODMAC | 12 | "Don't Stop" pop band that released a self-titled album in both 1968 and 1975: 2 wds. |
| 45% | LITTLEEVA | 9 | Pop singer whose version of "The Loco-Motion" inspired a dance craze in the 1960s: 2 wds. |
| 45% | TAYLORSWIFT | 11 | "Cardigan" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 45% | LADYGAGA | 8 | "Shallow" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 45% | NICKJONAS | 9 | "Jealous" pop singer who both hosted and was the musical act in a 2021 "SNL" episode: 2 wds. |
| 45% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 44% | ARIANAGRANDE | 12 | "7 Rings" singer who reimagined 18-Across in a 2024 hit with the same title: 2 wds. |
| 44% | PARAMORE | 8 | "Ain't It Fun" alternative band who released a self-titled #1 album in 2013 |
| 44% | EVANESCENCE | 11 | "Bring Me to Life" rock band who released a self-titled #1 album in 2011 |
| 44% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 44% | DURANDURAN | 10 | "Rio" New Wave band that released a self-titled album in both 1981 and 1993: 2 wds. |
| 43% | CARLYRAEJEPSEN | 14 | "Call Me Maybe" singer who released her sixth studio album, "The Loneliest Time," in 2022 (3 wds.) |
| 43% | LUISFONSI | 9 | Singer who hit #1 in 2017 with the Spanish/English-language "Despacito": 2 wds. |
| 42% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 42% | GUYLAFLEUR | 10 | Former Montreal Canadiens player considered one of the greatest NHL players of all time, who released his own disco album: 2 wds. |
| 42% | LADYGAGA | 8 | 15-Across, 9-Down, and 22-Down singer who released the studio album "Mayhem" in 2025 (2 wds.) |
| 42% | JOSEPHCOTTEN | 12 | Actor who played a reporter and friend of the title character in 17-Across: 2 wds. |
| 42% | NELLYFURTADO | 12 | Singer who released "I'm Like a Bird" in 2000: 2 wds. |
| 42% | ARIANAGRANDE | 12 | "Thank U, Next" pop singer who got her seventh #1 hit with a remix of 38-Across: 2 wds. |