| 100% | CALVINHARRIS | 12 | Rihanna's longest-running number one single "We Found Love" was written by ___, famed Scottish DJ, singer and songwriter: 2 wds. |
| 30% | STEVIENICKS | 11 | American singer and songwriter who became the first woman to be inducted twice into the Rock and Roll Hall of Fame: 2 wds. |
| 29% | STEPHENSTILLS | 13 | American singer and songwriter who is the first artist to be inducted twice on the same night into the Rock and Roll Hall of Fame: 2 wds. |
| 29% | WHITNEYHOUSTON | 14 | Singer and actress who played Rachel Marron in 18a and whose cover of "I Will Always Love You" became a best-selling single: 2 wds. |
| 27% | WHIPPINGPOST | 12 | 1969 song written by the late Gregg Allman that begins, "I've been run down and I've been lied to" (2 wds.) |
| 26% | COFFEESONG | 10 | "The ___," song written by Bob Hilliard and Dick Miles which was recorded by Frank Sinatra in 1946: 2 wds. |
| 26% | IAM | 3 | "___ Mine," 2002 song written by Eddie Vedder which was the first single of the album "Riot Act": 2 wds. |
| 25% | CALVIN | 6 | __ Harris; We Found Love Scottish DJ |
| 25% | WEFOUNDLOVE | 11 | Single from Rihanna's 6th studio album, a collaboration with DJ Calvin Harris, that won her a Grammy and was featured in "Sherlock" : 3 wds. |
| 25% | BETTERMAN | 9 | 1994 song written by Eddie Vedder which peaked at number one for eight weeks on Billboard Mainstream Rock: 2 wds. |
| 24% | KELLYCLARKSON | 13 | One Direction's "Tell Me a Lie" was written by ___, winner of the first season of "American Idol": 2 wds. |
| 24% | OZZYOSBOURNE | 12 | Heavy metal singer and reality TV star who is "catching some Z's": 2 wds. |
| 24% | LOVEYOURSELF | 12 | Justin Bieber's acoustic pop song written by him along with Ed Sheeran and Benny Blanco which was the seventh best-selling song of 2016: 2 wds. |
| 24% | HAPPY | 5 | 2013 song by Pharrell Williams that is on the soundtrack of "Despicable Me 2" and was Billboard's number-one single in 2014 |
| 23% | BLOOD | 5 | "Flesh and ___," 1970 single by Johnny Cash that was number one on the US Country Singles chart |
| 23% | JUSTINBIEBER | 12 | Canadian singer and teen sensation whose journey is often compared to Paul Anka's (birthday today): 2 wds. |
| 23% | RINASAWAYAMA | 12 | Singer/songwriter and model who was one of "Vogue" Japan's 2019 women of the year (2 wds.) |
| 23% | PITNEY | 6 | Gene —, US singer-songwriter whose UK top ten singles include Just One Smile and Backstage |
| 23% | PITNEY | 6 | Gene -, US singer-songwriter whose UK top ten singles include Just One Smile and Backstage |
| 23% | WHIPPINGPOST | 12 | 1969 song written by Gregg Allman that begins, "I've been run down / I've been lied to" (2 wds.) |
| 23% | MARGARETCOURT | 13 | Former World number one tennis player with 11 Women's Singles titles in the tournament mentioned in 17a: 2 wds. |
| 23% | ROYEMERSON | 10 | Former World number one tennis player with 6 Men's Singles titles in the tournament mentioned in 17a: 2 wds. |
| 23% | JOHNLEGEND | 10 | "All of Me" singer and "The Voice" coach who was named People's Sexiest Man Alive in 2019: 2 wds. |
| 23% | PAULMCCARTNEY | 13 | Singer and bass guitarist for the Beatles who was knighted in 1997: 2 wds. |
| 23% | MARIEOSMOND | 11 | Singer and talk show host who has been a spokesperson for Nutrisystem: 2 wds. |
| 23% | RIHANNA | 7 | Umbrella, Diamonds and We Found Love singer |
| 22% | SHAQUILLEONEAL | 14 | Basketball player whose jersey number was retired by the Lakers and the Heat: 2 wds. |
| 22% | NATETHURMOND | 12 | Basketball player whose jersey number was retired by the Cavaliers and the Warriors: 2 wds. |
| 22% | TAKEITEASY | 10 | Song co-written by Jackson Browne which was Eagles' first single that became one of their signature songs: 3 wds. |
| 22% | CLYDEDREXLER | 12 | Basketball player whose jersey number was retired by the Trail Blazers and the Rockets: 2 wds. |