| 100% | GRACEKELLY | 10 | English singer Mika's song which is titled after "The Country Girl" actress and uses dialogue from the movie: 2 wds. |
| 48% | 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. |
| 35% | LADYGAGA | 8 | Singer-songwriter whose song "Shallow" from the movie "A Star Is Born" won her an Oscar in 2018: 2 wds. |
| 34% | BEOUR | 5 | With 35-Across, Oscar-nominated song from Disney's "Beauty and the Beast" that lost to that movie's title song: 2 wds. |
| 34% | LONELYBOY | 9 | Hit song by Paul Anka which was also used as the title of the documentary made on him: 2 wds. |
| 32% | UMATHURMAN | 10 | American band "Fall Out Boy" hit which is named after the "Kill Bill" actress whose role also inspired the lyrics: 2 wds. |
| 32% | GALWAY | 6 | "___ Girl," song by English singer Ed Sheeran which has the name of an Irish city in its title that is home to Eyre Square |
| 32% | SAMSMITH | 8 | Singer-songwriter whose song "Writing's on the Wall" from the movie "Spectre" won him an Oscar in 2015: 2 wds. |
| 32% | INACROWN | 8 | "You Should See Me ___," Billie Eilish song released in 2018 and the title of which was inspired by a scene from "Sherlock": 3 wds. |
| 32% | ZOOEYDESCHANEL | 14 | "New Girl" actress and lead singer of the band She & Him: 2 wds. |
| 31% | TAYLORSWIFT | 11 | Seven-time Grammy-winning country and pop singer who was EW's 2010 Entertainer of the Year: 2 wds. |
| 31% | BOBDYLAN | 8 | Singer-songwriter whose song "Things Have Changed" from the movie "Wonder Boys" won him an Oscar in 2000: 2 wds. |
| 31% | KIDROCK | 7 | Rap and country singer with the song "Bawitdaba": 2 wds. |
| 31% | ASI | 3 | "___ Lay Dying," 1930 novel by William Faulkner, the title of which is derived from Homer's "Odyssey": 2 wds. |
| 31% | SUEME | 5 | Snide challenge which was also the name of a song on "Guys and Dolls": 2 wds. |
| 30% | SHIRLEYBASSEY | 13 | Singer of the James Bond theme songs "Goldfinger," "Diamonds Are Forever," and "Moonraker": 2 wds. |
| 30% | IAMSAM | 6 | 2001 drama which uses The Beatles' music and which has several characters whose names come from the band's songs: 3 wds. |
| 30% | JOHNLENNON | 10 | English songwriter who co-founded the Beatles and is known for his song "Imagine": 2 wds. |
| 30% | SHELLEYFABARES | 14 | Actress and singer who's the niece of 19-Across: 2 wds. |
| 30% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 30% | JENNIFERLOPEZ | 13 | "Selena" singer and actress who plays an ex-assassin in the new movie "The Mother": 2 wds. |
| 30% | BLAKESHELTON | 12 | Country singer and "The Voice" judge who is People's Sexiest Man Alive of 2017: 2 wds. |
| 30% | CABCALLOWAY | 11 | Big-band leader and jazz singer whose signature song was "Minnie the Moocher": 2 wds. |
| 30% | FLORIDA | 7 | Rapper and singer whose name comes from the state he was born in: 2 wds. |
| 30% | EASTERNCOUGAR | 13 | A subspecies of puma from North America which was formally declared extinct by the U.S. Fish and Wildlife Service in 2018: 2 wds. |
| 30% | EMMATHOMPSON | 12 | Actress who plays the protagonist in "Nanny McPhee and the Big Bang," which is based on the "Nurse Matilda" books: 2 wds. |
| 30% | MRSROBINSON | 11 | Song by Simon & Garfunkel which was included in the 1967 film "The Graduate" and originally appeared on the album "Bookends": 2 wds. |
| 30% | FAITHHILL | 9 | Country singer whose song "Breathe" was named the #1 single on Billboard's year-end countdown in 2000 (2 wds.) |
| 29% | APTPUPIL | 8 | Brad Renfro and Ian McKellen star in this movie which is based on a Stephen King novella and is directed by Bryan Singer: 2 wds. |
| 29% | HAWAII | 6 | "Blue ___," hit song that was used in Elvis Presley's titular movie which has the name of Barack Obama's birth state in its title |