| 100% | JONASBROTHERS | 13 | Artists on "Songland" whose "Sucker" was a #1 Billboard hit in 2019: 2 wds. |
| 46% | HARRIETTUBMAN | 13 | She was a conductor on the Underground Railroad, and her story was told in a 2019 film: 2 wds. |
| 46% | JOHNLEGEND | 10 | Artist on "Songland" whose "Glory," with Common, won an Oscar for Best Song in 2015: 2 wds. |
| 45% | WITHOUTYOU | 10 | 2020 song by the Kid Laroi whose remix was a top 10 hit in 2021: 2 wds. |
| 43% | EYESCLOSED | 10 | 2023 single by 49-Across that was a #1 hit on the "Billboard" Adult Top 40 chart (2 wds.) |
| 41% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 40% | MARIAHCAREY | 11 | Her 2009 hit "Obsessed" reentered the Billboard charts in 2019 thanks to a viral dance challenge video: 2 wds. |
| 40% | AGORAHILLS | 10 | 2023 Doja Cat hit whose title is a tribute to a town she lived in: 2 wds. |
| 40% | JANETJACKSON | 12 | Singer whose "Escapade" was a #1 song for three weeks in 1990 (2 wds.) |
| 40% | THEENTERTAINER | 14 | Scott Joplin instrumental song that was a hit in 1974: 2 wds. |
| 39% | TRUTHHURTS | 10 | Lizzo hit of 2019 whose title's only vowels are U's: 2 wds. |
| 39% | WAP | 3 | 2020 No. 1 hit whose title acronym is compared to “macaroni in a pot” |
| 39% | SNOW | 4 | "___ (Hey Oh)," 2006 Red Hot Chili Peppers song that was a No. 1 hit on the Billboard Modern Rock chart |
| 38% | JAMIEFOXX | 9 | "Django Unchained" actor who was a featured player on "In Living Color": 2 wds. |
| 38% | BILLIEEILISH | 12 | First artist born in the two-thousands to reach No. 1 on the Billboard Hot 100 (August, 2019) |
| 38% | SINEADOCONNOR | 13 | Singer whose "Nothing Compares 2 U" was a #1 song for four weeks in 1990 (2 wds.) |
| 37% | TRAVISSCOTT | 11 | Artist who had a top 10 Billboard hit with "Stargazing": 2 wds. |
| 37% | BRENDALEE | 9 | Artist whose Christmas song beat "All I Want for Christmas Is You" to No. 1 on the Billboard charts this month |
| 37% | PRINCE | 6 | Singer whose "Purple Rain" and a greatest hits compilation were Billboard's top two albums on May 7, 2016 |
| 37% | MARIAHCAREY | 11 | Singer with 18 #1 Billboard hits, more than any other solo artist since Elvis Presley: 2 wds. |
| 37% | CHER | 4 | Only artist to have a #1 hit on any Billboard chart in six consecutive decades |
| 37% | JIMCARREY | 9 | "The Truman Show" actor who was a featured player on "In Living Color": 2 wds. |
| 37% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 37% | IFEELFORYOU | 11 | Grammy-winning song written by Prince that was a #1 hit for Chaka Khan in 1984 (4 wds.) |
| 37% | IFI | 3 | "___ Were A Boy," 2008 Beyonce hit: 2 wds. |
| 37% | ALANNAHMYLES | 12 | Singer whose "Black Velvet" was a #1 song for two weeks in 1990 (2 wds.) |
| 37% | KENDRICKLAMAR | 13 | Artist who had a top 10 Billboard hit with "All the Stars": 2 wds. |
| 37% | RAPGOD | 6 | 2013 Eminem hit whose lyrics have a record-setting 1,560 words: 2 wds. |
| 37% | ICECREAM | 8 | 2020 Blackpink and Selena Gomez hit whose title is a sweet treat: 2 wds. |
| 36% | LEANONME | 8 | Song that was a #1 hit for Bill Withers in 1972 and for Club Nouveau in 1987: 3 wds. |