| 100% | RUNTHISTOWN | 11 | 2009 single from Jay-Z, featuring Rihanna and Kanye West, that won the trio many awards, including two Grammys and an Emmy : 3 wds. |
| 35% | JEAN | 4 | "Billie ___," the second single from Michael Jackson's album in 16a, that won two Grammys and one American Music Award |
| 34% | EMPIRESTATEOF | 13 | "___ Mind," a 2009 hit single from Jay-Z's 11th album that featured vocals from Alicia Keys : 3 wds. |
| 34% | WEFOUNDLOVE | 11 | Single from Rihanna's 6th studio album, a collaboration with DJ Calvin Harris, that won her a Grammy and was featured in "Sherlock" : 3 wds. |
| 32% | HAM | 3 | First single from Jay-Z and Kanye West's album "Watch the Throne" (2011) |
| 32% | POPSTYLE | 8 | Single off of 34-Across, featuring Kanye West and Jay Z: 2 wds. |
| 31% | WATCHTHETHRONE | 14 | 2011 Kanye West and Jay Z album with the song "Otis": 3 wds. |
| 30% | WAITFORU | 8 | #1 hit by Future featuring Drake and Tems that won the 2023 BET Best Collaboration Award: 3 wds. |
| 30% | RESTOFMYLIFE | 12 | Hit single from Ludacris, featuring Usher and David Guetta, that was included as part of the soundtrack for "Fast & Furious 6": 4 wds. |
| 30% | THENEWDANGER | 12 | The second album by rapper Mos Def, which was also certified gold and contained the single "Sunshine," featuring Kanye West: 3 wds. |
| 30% | KILLINTIME | 10 | Album by 45-Across featuring the singles 18-Across and 26-Across that won the 1989 Album of the Year Academy of Country Music Award (2 wds.) |
| 29% | IWISHYOUWOULD | 13 | Single from American musician DJ Khaled featuring Kanye West and Rick Ross: 4 wds. |
| 29% | KNOWNOBETTER | 12 | Major Lazer song featuring Travis Scott, Camila Cabello, and Quavo that won the 2017 Teen Choice Award for Choice Electronic/Dance Song (3 wds.) |
| 29% | KISSMEMORE | 10 | 50-Across and SZA hit single that won Best Pop Duo/Group Performance at the 2022 Grammy Awards (3 wds.) |
| 29% | ANDTHECITY | 10 | "Sex ___," American television show that won the Primetime Emmy Award for Outstanding Comedy Series in 2001: 3 wds. |
| 29% | 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 |
| 29% | JAIL | 4 | Song by Kanye featuring Jay-Z that won the Grammy Award for Best Rap Song in 2022 |
| 28% | ABETTERMAN | 10 | #1 song by 45-Across from 35-Across that won the 1989 Single of the Year Academy of Country Music Award (3 wds.) |
| 28% | TALKTHATTALK | 12 | Single from Rihanna's 6th studio album, a collaboration with Jay-Z, that got her a 2013 Grammy nomination : 3 wds. |
| 27% | MENATWORK | 9 | 15-Across and 33-Across rock band from Australia that won Best New Artist at the 1983 Grammy Awards (3 wds.) |
| 27% | HOTLINEBLING | 12 | Lead single from Drake's fourth album "Views," that won him two Grammys in 2017: 2 wds. |
| 27% | IMTHEONE | 8 | Single from DJ Khaled's "Grateful," featuring Justin Bieber, Quavo, Chance the Rapper and 16a: 3 wds. |
| 27% | LETITGO | 7 | Song from "Frozen", which won a Grammy and an Academy Award: 3 wds. |
| 27% | LEBRONJAMES | 11 | Heat forward who won the NBA Most Valuable Player award in 2009, 2010, 2012, and 2013: 2 wds. |
| 27% | IMTHEONE | 8 | Single from DJ Khaled's "Grateful," featuring Justin Bieber, Quavo, and Chance the Rapper: 3 wds. |
| 27% | SPACECOWBOY | 11 | Single from the album "Golden Hour" that won Best Country Song at the 2019 Grammys: 2 wds. |
| 27% | BUILDASNOWMAN | 13 | "Do You Want to ___", catchy song from "Frozen" that is the second most best-selling Christmas/holiday single: 3 wds. |
| 26% | ACTAFOOL | 8 | Single from Ludacris that was part of the soundtrack for "2 Fast 2 Furious," and was also nominated for a Grammy: 3 wds. |
| 26% | RAISINGSAND | 11 | Bluegrass album by Robert Plant and Alison Krauss that won Album of the Year at the 2009 Grammy Awards (2 wds.) |
| 26% | FIGHTFORYOU | 11 | H.E.R. song from "Judas and the Black Messiah" that won the Oscar for Best Original Song in 2021: 3 wds. |