| 100% | THEWEEKND | 9 | Stage name of "Starboy" singer who used the name for anonymity on YouTube: 2 wds. |
| 53% | ELTONJOHN | 9 | Stage name for the "Tiny Dancer" singer who was born Reginald Kenneth Dwight: 2 wds. |
| 50% | TORIKELLY | 9 | "Nobody Love" singer who first started posting videos on YouTube at the age of 14: 2 wds. |
| 49% | SARABAREILLES | 13 | Singer/songwriter who wrote music and lyrics for the stage adaptation of "Waitress" (2 wds.) |
| 48% | NANCYSINATRA | 12 | "These Boots Were Made for Walkin'" singer who sang on an episode of "The Sopranos": 2 wds. |
| 48% | ZAYNMALIK | 9 | One Direction singer who changed the spelling of his first name: 2 wds. |
| 47% | SARABAREILLES | 13 | Singer-songwriter who wrote music and lyrics for the stage adaptation of the film "Waitress" (2 wds.) |
| 46% | JAMESBROWN | 10 | Rock singer who was the subject of the 2014 biopic "Get On Up": 2 wds. |
| 46% | MILEYCYRUS | 10 | "Wrecking Ball" singer who performs on the remix of 49-Across: 2 wds. |
| 46% | GARTHBROOKS | 11 | "The Dance" country singer named the ACM Artist of the Decade for the 1990s: 2 wds. |
| 46% | GARTHBROOKS | 11 | "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds. |
| 46% | GARTHBROOKS | 11 | "The Dance" country singer who won the 2019 CMA for Entertainer of the Year: 2 wds. |
| 45% | GARTHBROOKS | 11 | "The River" singer who won the CMA Award for Entertainer of the Year seven times: 2 wds. |
| 45% | KESHA | 5 | Pop singer who used to use a dollar sign for the third letter of her name |
| 45% | PATTILABELLE | 12 | "New Attitude" singer who was the Flower on season 2 of "The Masked Singer": 2 wds. |
| 45% | JASONALDEAN | 11 | 17-Across and 30-Across country singer who was named ACM's Artist of the Decade for the 2010s (2 wds.) |
| 45% | BILLIEEILISH | 12 | "Bad Guy" singer who received the Grammys for both Album of the Year and Best New Artist in 2020: 2 wds. |
| 45% | DIONNEWARWICK | 13 | "Walk On By" singer who was the Mouse on season 3 of "The Masked Singer": 2 wds. |
| 45% | SAMSMITH | 8 | Nonbinary singer who won an Oscar for the Bond theme "Writing's on the Wall": 2 wds. |
| 45% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 45% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 45% | TAYLORSWIFT | 11 | "Lavender Haze" singer who won the People's Choice Award for Female Artist of 2022: 2 wds. |
| 45% | DWIGHTHOWARD | 12 | Basketball player who was the Octopus on season 6 of "The Masked Singer": 2 wds. |
| 45% | MIRANDALAMBERT | 14 | "Vice" singer who came in third on the first season of "Nashville Star": 2 wds. |
| 45% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 44% | GLADYSKNIGHT | 12 | "Midnight Train to Georgia" singer who was the Bee on season 1 of "The Masked Singer": 2 wds. |
| 44% | JASONALDEAN | 11 | "You Make It Easy" country singer named the ACM Artist of the Decade for the 2010s: 2 wds. |
| 44% | GEORGESTRAIT | 12 | "I Cross My Heart" country singer named the ACM Artist of the Decade for the 2000s: 2 wds. |
| 44% | TONYBENNETT | 11 | "Rags to Riches" singer who won the 2017 Library of Congress Gershwin Prize for Popular Song: 2 wds. |
| 44% | HARRYSTYLES | 11 | "As It Was" singer who won the People's Choice Award for Male Artist of 2022: 2 wds. |