| 100% | MARIAHCAREY | 11 | Her 2009 hit "Obsessed" reentered the Billboard charts in 2019 thanks to a viral dance challenge video: 2 wds. |
| 64% | FLEETWOODMAC | 12 | Their 1977 hit "Dreams" reentered the Billboard charts in 2020 thanks to a viral skateboarding video: 2 wds. |
| 60% | PHILCOLLINS | 11 | His 1981 hit "In the Air Tonight" reentered the Billboard charts in 2020 thanks to a viral reaction video: 2 wds. |
| 32% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 32% | GOODASHELL | 10 | Song on 46-Across's EP "Coconut Oil" that became a Billboard hit after she performed it at the 2019 MTV Video Music Awards (3 wds.) |
| 30% | BLACKPANTHER | 12 | Superhero movie whose soundtrack topped the Billboard charts in 2018: 2 wds. |
| 30% | LESMISERABLES | 13 | Musical drama whose soundtrack topped the Billboard charts in 2013: 2 wds. |
| 30% | BIGOLEFREAK | 11 | 2019 Megan Thee Stallion hit that was her first song to make the Billboard charts (3 wds.) |
| 29% | SUICIDESQUAD | 12 | Comic book movie whose soundtrack topped the Billboard charts in 2016: 2 wds. |
| 29% | ALLIWANTFOR | 11 | With 33-Across, holiday tune that hit #1 on the Billboard charts in 2019, 2020, and 2021: 4 wds. |
| 27% | BADROMANCE | 10 | A 2009 hit by Lady Gaga which won two Grammys and has gone on to become one of the best selling singles of all time: 2 wds |
| 27% | MARIAHCAREY | 11 | "Emotions" singer who received the Billboard Icon Award in 2019: 2 wds. |
| 27% | BADROMANCE | 10 | 2009 song by Lady Gaga that made her the first female in British chart history to have three number-one singles in one year: 2 wds. |
| 27% | GOODCOP | 7 | Police officer who talks to a suspect before the "bad" version steps in: 2 wds. |
| 26% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 26% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 26% | BESTIEVERHAD | 12 | 2009 Drake hit that went to #1 on the Billboard R&B and Rap charts: 4 wds. |
| 26% | CARLOSSANTANA | 13 | "Oye Como Va" musician who received the Billboard Latin Music Lifetime Achievement Award in 2009: 2 wds. |
| 25% | SUMMERSIXTEEN | 13 | 2016 Drake hit that went to #1 on the Billboard R&B and Rap charts: 2 wds. |
| 25% | HOTLINEBLING | 12 | 2015 Drake hit that went to #1 on the Billboard R&B and Rap charts: 2 wds. |
| 25% | MARIAHCAREY | 11 | Singer whose song "We Belong Together" peaked at number one on the Billboard Hot 100 chart in 2005: 2 wds. |
| 25% | OZONELAYER | 10 | Shielding region in the stratosphere, that has a hole thanks to human activities: 2 wds. |
| 25% | RICKYMARTIN | 11 | Singer whose song "Livin' La Vida Loca" peaked at number one on the Billboard Hot 100 chart in 1999: 2 wds. |
| 25% | IFALLAPART | 10 | Song by 42-Across that became a hit after a live-performance video went viral in 2017 (3 wds.) |
| 25% | AGORAHILLS | 10 | 2023 Doja Cat hit whose title is a tribute to a town she lived in: 2 wds. |
| 25% | JONASBROTHERS | 13 | Artists on "Songland" whose "Sucker" was a #1 Billboard hit in 2019: 2 wds. |
| 24% | MAGGIEROGERS | 12 | Singer/songwriter whose big break came when a video featuring Pharrell Williams listening to her song "Alaska" went viral in 2016 (2 wds.) |
| 24% | WHATSNEXT | 9 | Drake song that hit #1 on the Billboard Hot 100 in 2021: 2 wds. |
| 24% | ALTHEAGIBSON | 12 | In 1957, she became the first person of color to win a Wimbledon championship (2 wds.) |
| 24% | RIO | 3 | She “dances on the sand” in a Duran Duran hit |