| 100% | MAJORLAZER | 10 | Artist whose "Cold Water" debuted at #2 in August 2016: 2 wds. |
| 62% | KENDRICKLAMAR | 13 | Artist whose "Humble" debuted at #2 in April 2017: 2 wds. |
| 62% | POSTMALONE | 10 | Artist whose "Rockstar" debuted at #2 in October 2017: 2 wds |
| 47% | NICKIMINAJ | 10 | Rapper whose song "Anaconda" peaked at #2 on the Billboard Hot 100 in August 2014: 2 wds. |
| 46% | PAULCEZANNE | 11 | French artist whose "The Card Players" sold at auction for a record $250 million in 2011: 2 wds. |
| 46% | JUSTINBIEBER | 12 | 2010 American Music Awards New Artist of the Year whose fifth studio album, "Changes," debuted at #1 on the U.S. "Billboard" 200 in 2020 (2 wds.) |
| 46% | ARIANAGRANDE | 12 | 2013 American Music Awards New Artist of the Year whose sixth studio album, "Positions," debuted at #1 on the U.S. "Billboard" 200 in 2020 (2 wds.) |
| 45% | JONASBROTHERS | 13 | 2008 American Music Awards New Artist of the Year whose fifth studio album, "Happiness Begins," debuted at #1 on the U.S. "Billboard" 200 in 2019 (2 wds.) |
| 44% | GUSTAVKLIMT | 11 | Austrian artist whose "Portrait of Adele Bloch-Bauer I" sold at auction for a record $135 million in 2006: 2 wds. |
| 43% | TUPACSHAKUR | 11 | Rapper whose hologram performed at Coachella in 2012: 2 wds. |
| 42% | SUICIDESQUAD | 12 | Comic book movie whose soundtrack topped the Billboard charts in 2016: 2 wds. |
| 41% | JONASBROTHERS | 13 | Artists on "Songland" whose "Sucker" was a #1 Billboard hit in 2019: 2 wds. |
| 41% | MARIACALLAS | 11 | Opera singer whose hologram performed at Lincoln Center in 2018: 2 wds. |
| 41% | DAVIDBOWIE | 10 | Rock singer whose posthumous album "Blackstar" topped the charts in 2016: 2 wds. |
| 40% | CAROLBURNETT | 12 | Comedian and actress whose skit show debuted on CBS in September 1967 (2 wds.) |
| 40% | MATTDAMON | 9 | "The Martian" actor whose charitable foundation provides drinking water in developing regions: 2 wds. |
| 40% | MICHAELJACKSON | 14 | Pop singer whose hologram performed at the Billboard Music Awards in 2014: 2 wds. |
| 40% | JOHNLEGEND | 10 | Artist on "Songland" whose "Glory," with Common, won an Oscar for Best Song in 2015: 2 wds. |
| 40% | JASCHAHEIFETZ | 13 | Lithuanian-born violinist who, in 1917, made his Carnegie Hall debut at 16 years old: 2 wds. |
| 40% | LAURYNHILL | 10 | Singer whose 1998 song "Doo Wop (That Thing)" debuted at #1: 2 wds. |
| 40% | BRITNEYSPEARS | 13 | Singer whose 2011 song "Hold It Against Me" debuted at #1: 2 wds. |
| 40% | PEOPLESCHOICE | 13 | Award 18-Across won in January 2016 as Favorite Breakout Artist: 2 wds. |
| 40% | LIMPBIZKIT | 10 | Band whose "Chocolate Starfish and the Hot Dog Flavored Water" album went platinum in one week: 2 wds. |
| 39% | KACEYMUSGRAVES | 14 | Artist whose album "Golden Hour" won Album of the Year at the 2019 Grammys: 2 wds. |
| 39% | MEGHANTRAINOR | 13 | "All About That Bass" singer who won a Best New Artist Grammy in 2016: 2 wds. |
| 39% | BENPLATT | 8 | Tony-winning Best Actor of 16-Across whose film debut was in "Pitch Perfect": 2 wds. |
| 39% | JASONALDEAN | 11 | Country singer whose album "They Don't Know" topped the Billboard 200 in 2016: 2 wds. |
| 39% | PABLOPICASSO | 12 | Spanish cubist artist whose antiwar painting "Guernica" was in response to a Nazi bombing: 2 wds. |
| 39% | DAFTPUNK | 8 | French electronic duo whose 2013 album "Random Access Memories" debuted at #1: 2 wds. |
| 39% | CELINEDION | 10 | Singer whose 1998 song "My Heart Will Go On" debuted at #1: 2 wds. |