| 100% | OHPRETTYWOMAN | 13 | 1964 Roy Orbison hit that has almost the same title as, and is featured in, a 1990 Julia Roberts film (3 wds.) |
| 68% | ONLYTHELONELY | 13 | 1960 Roy Orbison hit that has the same title as, and is featured in, a 1991 John Candy film (3 wds.) |
| 60% | RUNNINGSCARED | 13 | 1961 Roy Orbison hit that has the same title as, but is not featured in, a 1986 Gregory Hines/Billy Crystal film (2 wds.) |
| 36% | SOMENIGHTS | 10 | #3 fun. hit with the same title as the album that 14-, 19- and 44-Across are on: 2 wds. |
| 34% | BLUEBAYOU | 9 | Roy Orbison song that was a #3 hit for 32-Across in 1977: 2 wds. |
| 33% | PRETTYWOMAN | 11 | 1990 film featuring Julia Roberts and a necklace with 23 rubies in heart-shaped diamonds (2 wds.) |
| 33% | PRETTYWOMAN | 11 | Film that features Julia Roberts and a necklace with 23 rubies in heart-shaped diamonds (2 wds.) |
| 33% | PRETTYWOMAN | 11 | 1990 Garry Marshall film starring 17-Across and 28-Across whose title was inspired by a Roy Orbison song (2 wds.) |
| 30% | VELVETREVOLVER | 14 | American hard rock supergroup that had Slash as a member and which produced the hit single "Slither": 2 wds. |
| 30% | RUNAWAYBRIDE | 12 | Rom-com starring Julia Roberts and Richard Gere that was one of the Top 10 box office hits of 1999 (2 wds.) |
| 29% | REACHOUTFORME | 13 | Song by Burt Bacharach and 26-Across that was a hit for 15-Across in 1964: 4 wds. |
| 29% | THEPOWEROFLOVE | 14 | No. 1 hit by Huey Lewis and the News that was featured in the 1985 film "Back to the Future" (4 wds.) |
| 29% | TENPINBOWLING | 13 | Popular sport played with a ball that has three holes and whose history has been traced back to the Egyptians living in 3200 BCE: 3 wds. |
| 29% | LADYMARMALADE | 13 | Song from the 2001 film "Moulin Rouge!" that was a #1 hit for Pink, Christina Aguilera, Lil' Kim, and Mya: 2 wds. |
| 29% | RESTOFMYLIFE | 12 | Hit single from Ludacris, featuring Usher and David Guetta, that was included as part of the soundtrack for "Fast & Furious 6": 4 wds. |
| 29% | WARTS | 5 | Bumps that are often seen on toads and also a feature of Shrek's anatomy as an ogre in the book |
| 29% | BADNEWSBEARS | 12 | Sports comedy, directed by Richard Linklater, based on an alcoholic baseball player and is also a reboot of 1976 film of the same name: 3 wds. |
| 28% | AZTECRUINS | 10 | Historical site in New Mexico that was declared as a U.S. National Monument in 1923 and has Ancestral Puebloan structures: 2 wds. |
| 28% | TIMOTHYDALTON | 13 | Actor from "Wuthering Heights", who has played James Bond in two films (as well as a third that was never released) : 2 wds. |
| 28% | OLIVERREED | 10 | Actor whose first name is the title of a Best Picture he co-starred in, and whose last name is that film's director |
| 27% | EATPRAYLOVE | 11 | Julia Roberts film set in Italy, India, and Indonesia (3 wds.) |
| 27% | DEADWOOD | 8 | National Historic Landmark District in South Dakota that is the setting and title of an HBO series and a 2019 film starring Timothy Olyphant and Ian McShane |
| 27% | IGETAROUND | 10 | 1964 Beach Boys hit that was the band's first #1 single: 3 wds. |
| 27% | KATHRYNSMITH | 12 | American football coach who has been actively involved as a full-time female coach in NFL history and has most recently served for the Buffalo Bills: 2 wds. |
| 27% | GAMEOFTHRONES | 13 | Drama that has featured Kit Harington and Rose Leslie, who married in 2018: 3 wds. |
| 27% | FREEDOM | 7 | A hit song by Pharrell Williams that was used in the film "Despicable Me 3" |
| 27% | TURNTURNTURN | 12 | 1965 #1 hit for the Byrds that had the subtitle "To Everything There Is a Season": 3 wds. |
| 27% | ALLMYCHILDREN | 13 | Soap opera that has featured Mark Consuelos and Kelly Ripa, who married in 1996: 3 wds. |
| 27% | THEWAYWEWERE | 12 | Title Streisand song featured in a 1973 film co-starring Robert Redford (4 wds.) |
| 27% | DONTYOUWANTME | 13 | The Human League song that was a No. 1 hit in 1982 (4 wds.) |