| 100% | JUSTIN | 6 | With 35-Across, "Yummy" singer who won the Pop Album of the Year Juno in 2011 and 2016 |
| 67% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 55% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 54% | BURTONCUMMINGS | 14 | Singer-songwriter in the Canadian Music Hall of Fame who won the 1979 Album of the Year Juno Award for "Dream of a Child" (2 wds.) |
| 54% | LEONARDCOHEN | 12 | Singer-songwriter in the Canadian Music Hall of Fame who won the 2017 Album of the Year Juno Award for "You Want It Darker" (2 wds.) |
| 53% | ADELE | 5 | One-named singer who won the 2016 Album of the Year |
| 51% | ANDRE | 5 | ___ Blake, Jamaican soccer player who won the MLS Goalkeeper of the Year Award in 2016 and 2020 |
| 49% | MARS | 4 | Singer Bruno who won Grammys for Record, Album, and Song of the Year in 2018 |
| 48% | NORAHJONES | 10 | "Come Away With Me" singer who received the Grammys for both Album of the Year and Best New Artist in 2003: 2 wds. |
| 47% | JONIMITCHELL | 12 | Singer-songwriter in the Canadian Music Hall of Fame who won the 2001 Vocal Jazz Album of the Year Juno Award for "Both Sides Now" (2 wds.) |
| 47% | BEYONCE | 7 | 14-Across, 8-Down, and 49-Across singer whose "Cowboy Carter" won Album of the Year at the Grammy Awards in 2025 |
| 46% | ADELE | 5 | British singer who won the Album of the Year Grammy in 2012 for "21" |
| 46% | BOB | 3 | ___ Dylan, American singer who won a Grammy for Album of the Year in 1973 |
| 46% | JENNIFERLOPEZ | 13 | "Let's Get Loud" singer who was named Glamour Woman of the Year in 1999 and 2011: 2 wds. |
| 46% | JON | 3 | ___ Batiste, "We Are" singer who won the Grammy Award for Album of the Year in 2022 |
| 46% | JAYJOHNSON | 10 | Head coach of 35-Across who won league championships with the University of Nevada in 2015 and the University of Arizona in 2021 (2 wds.) |
| 45% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 45% | DONOVAN | 7 | ___ Ricketts, Jamaican former soccer player who won the MLS Goalkeeper of the Year Award in 2010 and 2013 |
| 45% | KACEYMUSGRAVES | 14 | 19-Across and 46-Across singer who won four 2019 Grammys, including Album of the Year and Best Country Album for "Golden Hour" (2 wds.) |
| 45% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 45% | GAGA | 4 | Lady ___, singer who won the Video of the Year for "Bad Romance" at MTV Video Music Awards in 2011 |
| 44% | ADELE | 5 | She won Album of the Year honors in 2012 and 2017 |
| 44% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 44% | NORAHJONES | 10 | "Don't Know Why" singer who won the Best New Artist and Record of the Year Grammys in 2003: 2 wds. |
| 43% | BARENAKED | 9 | __ Ladies; won 2001 Juno for Pop Album of the Year |
| 43% | CHRISEVERT | 10 | Tennis player who won the AP Athlete of the Year award in 1974, 1975, 1977, and 1980: 2 wds. |
| 43% | SERENAWILLIAMS | 14 | Tennis player who won the AP Athlete of the Year award in 2002, 2009, 2013, and 2015: 2 wds. |
| 43% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 43% | MARENMORRIS | 11 | 1-Across, 12-Across, 27-Across, and 50-Across country/pop singer who was named Female Vocalist of the Year by the Country Music Association in 2020 (2 wds.) |
| 43% | KATY | 4 | Singer ___ Perry who won Video of the Year Award for "Firework" at MTV Video Music Awards in 2011 |