| 100% | CRUSH | 5 | Song by David Archuleta whose title denotes a state of infatuation |
| 42% | VALENTINE | 9 | Song by 5 Seconds of Summer whose title is usually a recipient of a heart-shaped card |
| 41% | LIKE | 4 | "I Really ___ You," song by Carly Rae Jepsen whose title is also a declaration of feelings |
| 40% | FAME | 4 | Title of a hit song by Irene Cara or David Bowie |
| 39% | ROAR | 4 | Song by Katy Perry whose title mimics a lion |
| 38% | PAM | 3 | "Polythene ___," 1969 song by The Beatles whose title was inspired by the nickname of a fan |
| 36% | IRIS | 4 | Song by Goo Goo Dolls whose title is part of an eye |
| 36% | AIR | 3 | "February ___," 2009 song by Lights whose title means a mixture of gases needed for breathing |
| 35% | ALASKA | 6 | State that's the title of a Maggie Rogers song |
| 35% | GLASS | 5 | With 27 Across, 2022 film whose title was inspired by a Beatles song |
| 35% | OKLAHOMA | 8 | State whose name is the title of a classic Broadway musical |
| 35% | AMILLI | 6 | Lil Wayne song whose title references a lot of money |
| 34% | OHIO | 4 | State that's the title of a Neil Young song (where Cleveland is) |
| 33% | UNDER | 5 | "___ Pressure," 1981 song by Queen and David Bowie which is a part of the album "Hot Space" |
| 33% | SHE | 3 | "April Come ___ Will," 1966 song by Simon & Garfunkel whose title refers to a woman |
| 33% | FLORIDA | 7 | U.S. state that's the title of a 2024 Taylor Swift song |
| 33% | TREE | 4 | "July ___," 1965 song by Nina Simone whose title means a woody tall plant |
| 33% | NOWHEREMAN | 10 | 1965 song whose title character "doesn't have a point of view" |
| 33% | TAKES | 5 | "It ___ Two," 1995 comedy movie starring the Olsen twins whose title is taken from a song by Marvin Gaye |
| 32% | IROCK | 5 | Boast formed by removing the middle two words of a popular Paul Simon song title |
| 32% | MIAMI | 5 | "Move to ___," hit song by Spanish singer Enrique Iglesias which has the name of a Florida city in its title |
| 32% | KISS | 4 | "___ Me," song by Ed Sheeran whose title is also "X" on a romantic card |
| 32% | HAPPY | 5 | 2011 song by Pharrell Williams whose title is also a word for being joyful and describes the emotion behind a smile |
| 32% | PRETTYWOMAN | 11 | 1990 Garry Marshall film starring 17-Across and 28-Across whose title was inspired by a Roy Orbison song (2 wds.) |
| 32% | LAYLA | 5 | Title character of a song inspired by both a seventh-century Persian story and George Harrison's then-wife |
| 32% | PETESAMPRAS | 11 | A retired American tennis legend whose record of 14 titles was only surpassed by Federer in 2009: 2 wds. |
| 31% | SWEETHOME | 9 | "___ Alabama," 1974 hit song by rock band, Lynyrd Skynyrd that inspired the title of a rom-com starring Reese Witherspoon: 2 wds. |
| 31% | ISIS | 4 | Bob Dylan song whose title is the name of a goddess |
| 31% | SULTANS | 7 | "___ of Swing," song by Dire Straits with a regal title |
| 31% | ALASKA | 6 | State whose flag, with eight gold stars in the shape of the Big Dipper, was designed by a 13-year-old |