| 100% | THEWAYWEWERE | 12 | 1973 romantic drama nominated for six Oscars starring 15-Across and directed by 49-Across (4 wds.) |
| 43% | WHENTHEYSEEUS | 13 | Emmy-nominated Netflix miniseries created by Ava DuVernay and starring 15-Across and 49-Across (4 wds.) |
| 41% | BOYZNTHEHOOD | 12 | 1991 Oscar-nominated film starring Ice Cube and Cuba Gooding Jr. directed by 30-Across (4 wds.) |
| 38% | ATREEGROWSIN | 12 | "___ Brooklyn," 1945 romantic drama film directed by Elia Kazan, starring Dorothy McGuire: 4 wds. |
| 38% | BEFORETRILOGY | 13 | Series of three romantic dramas written/directed by Richard Linklater and starring 18-Across and 44-Across (2 wds.) |
| 38% | PEARLHARBOR | 11 | 2001 American romantic period war drama film directed by Michael Bay and starring Ben Affleck: 2 wds. |
| 38% | JUSTGOWITHIT | 12 | 2011 romantic comedy film directed by Dennis Dugan which stars Nicole Kidman and Adam Sandler: 4 wds. |
| 38% | JUSTGOWITHIT | 12 | 2011 romantic comedy film directed by Dennis Dugan starring Jennifer Aniston and Adam Sandler: 4 wds. |
| 37% | RAMBLINGROSE | 12 | 1991 drama starring 16-Across and 39-Across that is the only film to have a mother and daughter both nominated for an Oscar for the same film (2 wds.) |
| 37% | THEWAYWEWERE | 12 | 1973 blockbuster romantic drama starring Barbra Streisand and Robert Redford (4 wds.) |
| 37% | OUTOFAFRICA | 11 | 1985 romantic drama starring 12-Across and based on a book written by 41-Across: 3 wds. |
| 36% | HEGOTGAME | 9 | 1998 basketball drama starring Denzel Washington and directed by Spike Lee: 3 wds. |
| 36% | MOBETTERBLUES | 13 | 1990 musical drama starring Denzel Washington and directed by Spike Lee: 3 wds. |
| 36% | RICHARDJEWELL | 13 | Oscar-nominated biographical drama directed by 46-Across (2 wds.) |
| 36% | FATAL | 5 | "___ Attraction," 1987 romantic thriller starring Michael Douglas that was nominated for six Oscars |
| 35% | AWARMDECEMBER | 13 | 1973 romance directed by and starring 43-Across as an American widow in London (3 wds.) |
| 35% | DEBORAHKERR | 11 | "The King and I" actress who was nominated for six Oscars but never won one: 2 wds. |
| 35% | REACHOUTFORME | 13 | Song by Burt Bacharach and 26-Across that was a hit for 15-Across in 1964: 4 wds. |
| 35% | CHARLIZETHERON | 14 | 15-Across and 29-Across star who won a Best Actress Oscar for "Monster" and who turns 45 today (2 wds.) |
| 34% | SIDNEYPOITIER | 13 | Star of 15- and 34-Across who won an Oscar for "Lilies of the Field": 2 wds. |
| 34% | MYSTERYOFLOVE | 13 | Song from 23-Across/37-Across written by 49-Across nominated for a 2018 Best Original Song Oscar (3 wds.) |
| 34% | EMERALDFENNELL | 14 | 16-Across, 22-Across, and 43-Across actress who was nominated for three Oscars for writing and directing "Promising Young Woman" (2 wds.) |
| 34% | PLAYMISTYFORME | 14 | 1971 thriller directed by and starring Clint Eastwood: 4 wds. |
| 34% | AWKWARDMOMENT | 13 | "That ___," 2014 romantic comedy-drama film directed by Tom Gormican and starring Zac Efron and Miles Teller: 2 wds. |
| 33% | TOEACHHISOWN | 12 | American romantic drama for which Hollywood's centenarian Olivia de Havilland won her first Oscar: 4 wds. |
| 32% | THINKLIKEAMAN | 13 | 2012 romantic comedy starring 15-Across: 4 wds. |
| 32% | FARANDAWAY | 10 | 1992 drama directed by Ron Howard, starring Tom Cruise and Nicole Kidman as Irish immigrants: 3 wds. |
| 32% | LADYBIRD | 8 | Greta Gerwig film starring Saoirse Ronan and Laurie Metcalf that was nominated for five Oscars (2 wds.) |
| 32% | OFTHELOSTARK | 12 | "Raiders ___," 1981 Indiana Jones film directed by Steven Spielberg and starring Harrison Ford: 4 wds. |
| 32% | GREYSANATOMY | 12 | ABC medical drama since 2005 starring 26-Across and created by 38-Across (2 wds.) |