| 100% | BREAKMYSOUL | 11 | Beyonce #1 hit that won the 2023 BET Viewer's Choice Award: 3 wds. |
| 61% | KILLBILL | 8 | SZA #1 hit that won the 2023 BET Video of the Year Award: 2 wds. |
| 57% | WAITFORU | 8 | #1 hit by Future featuring Drake and Tems that won the 2023 BET Best Collaboration Award: 3 wds. |
| 48% | ABOUTDAMNTIME | 13 | Lizzo song that won the People's Choice Award for Song of 2022: 3 wds. |
| 44% | FASTCAR | 7 | 1988 Tracy Chapman hit that won Song of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 42% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |
| 41% | RULEOFWOLVES | 12 | Novel by 40-Across that won the 2021 Goodreads Choice Award for Young Adult Fantasy (3 wds.) |
| 40% | JUSTLIKETHAT | 12 | Bonnie Raitt single that won the 2023 Grammy for Song of the Year: 3 wds. |
| 40% | BUSTARHYMES | 11 | "What's It Gonna Be?!" rapper who won the 2023 BET Lifetime Achievement Award: 2 wds. |
| 40% | WEFOUNDLOVE | 11 | Rihanna hit that won the 2013 Best Music Video Grammy: 3 wds. |
| 39% | BOOMBOOMPOW | 11 | Black Eyed Peas hit that won the 2010 Best Music Video Grammy: 3 wds. |
| 39% | STRANGERTHINGS | 14 | Netflix horror series that won the People's Choice Awards for the Show of 2019 and the Drama Show of 2019 (2 wds.) |
| 39% | 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.) |
| 38% | DONTWANNAFIGHT | 14 | Alabama Shakes song that won the Grammy Award for Best Rock Song in 2016: 3 wds. |
| 38% | BETTERCALLSAUL | 14 | AMC "Breaking Bad" prequel that won a Peabody Award in 2023: 3 wds. |
| 38% | ANDTHECITY | 10 | "Sex ___," American television show that won the Primetime Emmy Award for Outstanding Comedy Series in 2001: 3 wds. |
| 37% | BEFORETHEFALL | 13 | Noah Hawley novel that won the 2017 Edgar Award for Best Novel (3 wds.) |
| 37% | THELOCKARTIST | 13 | Steve Hamilton novel that won the 2011 Edgar Award for Best Novel (3 wds.) |
| 35% | WEAREYOUNG | 10 | #1 fun. hit released in 2011 that won the Grammy for Song of the Year: 3 wds. |
| 35% | THEROUNDHOUSE | 13 | Louise Erdrich novel that won the National Book Award for Fiction in 2012 (3 wds.) |
| 35% | LORDOFMISRULE | 13 | Jaimy Gordon novel that won the National Book Award for Fiction in 2010 (3 wds.) |
| 35% | THEECHOMAKER | 12 | 2006 novel by 32-Across that won the National Book Award for Fiction (3 wds.) |
| 35% | 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% | IGETAROUND | 10 | 1964 Beach Boys hit that was the band's first #1 single: 3 wds. |
| 35% | LONGTALLSALLY | 13 | 1956 Little Richard hit that's #55 on the Rolling Stone list: 3 wds. |
| 35% | FROMTHEFIRES | 12 | Greta Van Fleet album that won the Grammy Award for Best Rock Album in 2019 (3 wds.) |
| 34% | RAIN | 4 | "Purple ___," song that won the Favorite New Song Award at the 11th People's Choice Awards in 1985 |
| 34% | EMILYHENRY | 10 | 18-Across, 26-Across, and 35-Across novelist who won the 2021, 2022, and 2023 Goodreads Choice Award for Best Romance (2 wds.) |
| 34% | BEVERLY | 7 | "___ Hills Cop," movie that won the Favorite Motion Picture Award at the 11th People's Choice Awards in 1985 |
| 34% | DENVERNUGGETS | 13 | Northwest Division team that won the franchise's first-ever NBA Championship in 2023, after 56 years: 2 wds. |