| 100% | ARIANAGRANDE | 12 | "Thank U, Next" pop singer who got her seventh #1 hit with a remix of 38-Across: 2 wds. |
| 49% | THEWEEKND | 9 | "The Hills" R&B singer who got his seventh #1 hit with 38-Across: 2 wds. |
| 42% | NELLYFURTADO | 12 | Pop singer who had a crossover hit with her 2006 electropop song "Maneater" (2 wds.) |
| 40% | TAYLORSWIFT | 11 | Country singer who had a crossover hit with her 2008 pop song "Love Story" (2 wds.) |
| 38% | ARIANAGRANDE | 12 | "Thank U, Next" singer who is a guest judge on Season 15 of "RuPaul's Drag Race" (2 wds.) |
| 37% | ARIANAGRANDE | 12 | "Thank U Next" singer who sings "Met Him Last Night" with Demi Lovato on "Dancing with the Devil ... the Art of Starting Over" (2 wds.) |
| 36% | JOHNMELLENCAMP | 14 | "Jack & Diane" singer who had a hit in 1986 with "R.O.C.K. in the U.S.A.": 2 wds. |
| 36% | ARIANAGRANDE | 12 | "7 Rings" pop singer who partnered with Justin Bieber on the 2020 #1 song "Stuck With U": 2 wds. |
| 36% | LEEGREENWOOD | 12 | "I.O.U." singer who had a hit in 2001 with "God Bless the U.S.A.": 2 wds. |
| 36% | QUEENLATIFAH | 12 | Singer who spells out the title of her 1994 hit "U.N.I.T.Y.": 2 wds. |
| 35% | HARLEMSHAKE | 11 | Baauer hit with a record-setting 103.1 million US streams in the week of March 2, 2013: 2 wds. |
| 35% | GWENSTEFANI | 11 | Ska punk singer who had a crossover hit with her 2005 hip hop song "Hollaback Girl" (2 wds.) |
| 35% | ADAMLEVINE | 10 | American pop singer who shares a first name with older singer Ant: 2 wds. |
| 35% | MARIAHCAREY | 11 | Singer who duetted with Boyz II Men on 1995's "One Sweet Day," a #1 hit for 16 weeks: 2 wds. |
| 34% | ARETHAFRANKLIN | 14 | Singer who spells out the title of her 1967 hit "Respect": 2 wds. |
| 34% | ARIANAGRANDE | 12 | Singer who spells out the title of her 2019 hit "NASA": 2 wds. |
| 33% | SMOKEYROBINSON | 14 | Singer who performed "U Really Got a Hold on Me" (a parody of "You've Really Got a Hold on Me") on "Sesame Street": 2 wds. |
| 33% | ARIANAGRANDE | 12 | Singer of the #1 hits "Thank U, Next" and "7 Rings": 2 wds. |
| 33% | LUKECOMBS | 9 | Country singer who had a 2023 hit with his cover of Tracy Chapman's "Fast Car": 2 wds. |
| 33% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 33% | ARIANAGRANDE | 12 | "Thank U, Next" singer who's had seven songs debut at #1 on the Billboard Hot 100: 2 wds. |
| 33% | JIMMIEALLEN | 11 | "Best Shot" singer who collaborated with Brad Paisley on the 2021 country hit "Freedom Was a Highway": 2 wds. |
| 33% | ARIANAGRANDE | 12 | "7 Rings" singer who reimagined 18-Across in a 2024 hit with the same title: 2 wds. |
| 32% | JESSEMCCARTNEY | 14 | Pop singer with Dream Street who was the runner-up on season 3 of "The Masked Singer" as the Turtle: 2 wds. |
| 32% | SHERYLCROW | 10 | "All I Wanna Do" singer who collaborated with Kid Rock on his biggest pop hit, "Picture," in 2002: 2 wds. |
| 32% | MARYTRAVERS | 11 | Folk singer who, in a trio with Peter and Paul, sang the 1963 hit "Puff, the Magic Dragon": 2 wds. |
| 32% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 32% | DOLLYPARTON | 11 | "Jolene" singer who collaborated with Brad Paisley on the 2005 country hit "When I Get Where I'm Going": 2 wds. |
| 31% | SUSANBOYLE | 10 | "I Dreamed a Dream" singer who got her start on "Britain's Got Talent" in 2009: 2 wds. |
| 31% | SINEADOCONNOR | 13 | Irish singer who had the #1 hit "Nothing Compares 2 U": 2 wds. |