| 100% | DYLAN | 5 | Bob ___, singer who covered the song "Take a Message to Mary" in 1970 |
| 42% | BIEBER | 6 | Singer who gave his name to a "fever" in the 2010s |
| 39% | DAVIDBOWIE | 10 | "Space Oddity" singer who cowrote a song in "SpongeBob SquarePants: The Broadway Musical": 2 wds. |
| 39% | ENYA | 4 | Singer for whom a fish native to the Orinoco was named in 2017 |
| 39% | JOHNLEGEND | 10 | "All of Me" singer who wrote a song in "SpongeBob SquarePants: The Broadway Musical": 2 wds. |
| 38% | RODSTEWART | 10 | Singer who performed his song "Infatuation" to open the first MTV Video Music Awards, in 1984: 2 wds. |
| 37% | BONEY | 5 | ___ M., German-Caribbean vocal group who covered the Christmas song "Mary's Boy Child" in 1978 |
| 37% | CASSIDY | 7 | Eva ___, singer who covered "Over the Rainbow" in 1992 |
| 36% | SARABAREILLES | 13 | "Love Song" singer/pianist who performed a duet with 18-Across at the Grammy Awards in 2014 (2 wds.) |
| 36% | ENYA | 4 | One-named singer who co-composed a song in Elvish for "The Lord of the Rings" |
| 36% | MASTERSOFWAR | 12 | Song by Bob Dylan that was covered by Eddie Vedder to celebrate Dylan's 30 years in the music industry: 3 wds. |
| 36% | BASS | 4 | Singer who rarely gets the melody in a choir |
| 35% | ARIANA | 6 | ___ Grande, singer who covered "Over the Rainbow" at a 2017 benefit concert |
| 35% | TORME | 5 | Singer who once sang a song to Kramer on "Seinfeld" |
| 35% | PINBALLWIZARD | 13 | "Tommy" song sung by 47-Across that's the only cover of a Who song to reach the Top 10 (2 wds.) |
| 35% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 34% | ROLLTHEDICE | 11 | Take a chance ... or a hint to the letters in the shaded squares |
| 34% | CHER | 4 | Singer who was married to Sonny Bono and Gregg Allman in the 1970s |
| 34% | INDILA | 6 | French singer who released a song called "Love Story" in 2014 |
| 34% | CAREY | 5 | Mariah ___, singer who released a song called "Love Story" in 2008 |
| 34% | MYA | 3 | Single-named singer who had a role in the movie "Chicago" |
| 34% | DREWBARRYMORE | 13 | American singer SZA's song which is titled after a "Charlie's Angels" actress who also makes a cameo in the music video: 2 wds. |
| 34% | BEYONCE | 7 | Singer who appeared in a Pepsi commercial with her song "Grown Woman" in 2013 |
| 34% | BERRA | 5 | Yogi who said "When you come to a fork in the road, take it" |
| 34% | ADELE | 5 | Singer who won a Grammy Award for Song of the Year winner for "Hello" |
| 34% | ALI | 3 | Nadia ___, singer who also released a song called "Love Story" in 2009 |
| 34% | KESHA | 5 | "Blow" singer who used to have a dollar sign in her name |
| 34% | BJORK | 5 | Icelandic singer who wore a swan dress to the 2001 Academy Awards |
| 34% | BLOWININTHEWIND | 15 | Bob Dylan song ... or a hint to the object found by connecting the four circled letters in a diamond |
| 34% | HUEY | 4 | Singer Lewis with a cameo in "Back to the Future" |