| 100% | DONHO | 5 | Honolulu-born pop singer known for "Tiny Bubbles" (2 wds.) |
| 53% | THEWEEKND | 9 | Canadian singer known for "Can't Feel My Face": 2 wds. |
| 52% | BOBMARLEY | 9 | "One Love" singer known for wearing a crocheted Rastafarian hat: 2 wds. |
| 50% | JLO | 3 | Nickname of the singer known for "All I Have" and "On the Floor": 2 wds. |
| 49% | BRUNOMARS | 9 | "That's What I Like" singer known for wearing a fedora or a trucker's cap: 2 wds. |
| 49% | SIA | 3 | Pop singer known for wearing giant wigs |
| 48% | LADYGAGA | 8 | Pop singer known for her song Poker Face |
| 48% | SIA | 3 | Pop singer known for her face-obscuring wigs |
| 48% | SIA | 3 | Pop singer known for wearing face-covering wigs |
| 48% | SIA | 3 | Pop singer known for wigs that hide her face |
| 47% | SIA | 3 | Pop singer known for performing in a face-obscuring wig |
| 46% | BRUNOMARS | 9 | Grammy-winning pop singer born in October (2 wds.) |
| 46% | BAZLUHRMANN | 11 | Australian director of 19- and 33-Across who's known for films with pop music soundtracks: 2 wds. |
| 46% | BRYANADAMS | 10 | Canadian singer known for the hit songs "Summer of '69" and "Heaven" (2 wds.) |
| 46% | PHILCOLLINS | 11 | Known for his song "In the Air Tonight", this English singer led the rock band Genesis before going solo: 2 wds. |
| 45% | DONHO | 5 | "Tiny Bubbles" singer: 2 wds. |
| 45% | SELENAGOMEZ | 11 | Pop singer and "Wizards of Waverly Place" actress born 7/22/92 (2 wds.) |
| 44% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 43% | GEORGEMICHAEL | 13 | Known for his 1987 hit album "Faith", this English singer rose to fame as a member of music duo "Wham!" before going solo: 2 wds. |
| 43% | KATYPERRY | 9 | Starting in 2010, pop singer with a song in the top 10 of the Billboard Hot 100 for 69 consecutive weeks: 2 wds. |
| 43% | BILLYJOEL | 9 | American singer-songwriter known for his hit song "Piano Man": 2 wds. |
| 43% | ARIANAGRANDE | 12 | Pop singer playing Penny Pingleton in 30-Across: 2 wds. |
| 42% | ARTUROTOSCANINI | 15 | Conductor known for fighting fascism: 2 wds. |
| 42% | BRUNOMARS | 9 | Astronomer's favorite pop singer?: 2 wds. |
| 42% | CHARLESDARWIN | 13 | British scientist known for his theory of evolution: 2 wds. |
| 42% | GREGORMENDEL | 12 | Pioneering biologist known for his work in genetics: 2 wds. |
| 42% | CHARLESDARWIN | 13 | Pioneering biologist known for his theory of evolution: 2 wds. |
| 42% | RACHELCARSON | 12 | Pioneering biologist known for her book "Silent Spring": 2 wds. |
| 42% | PHILIPWHEELER | 13 | Miami Dolphins linebacker known for his long hair: 2 wds. |
| 42% | NYPOST | 6 | Big Apple paper known for its outrageous headlines: 2 wds. |