| 100% | VALENTINESDAY | 13 | 2010 hit romantic comedy costarring 15-Across: 2 wds. |
| 53% | THEHANGOVER | 11 | 2009 hit comedy starring 15-Across: 2 wds. |
| 47% | JASONBATEMAN | 12 | Jennifer Aniston's costar in the 2010 romantic comedy/drama "The Switch": 2 wds. |
| 45% | THINKLIKEAMAN | 13 | 2012 romantic comedy starring 15-Across: 4 wds. |
| 45% | GERARDBUTLER | 12 | Jennifer Aniston's costar in the 2010 romantic comedy/action film "The Bounty Hounter": 2 wds. |
| 44% | COUNTRYMUSIC | 12 | 2010 hit album by 44-Across (and his primary genre): 2 wds. |
| 43% | WEDDINGSINGER | 13 | With "The," Adam Sandler romantic comedy starring 33-Across: 2 wds. |
| 41% | ADATE | 5 | "Win ____ With Tad Hamilton!" (2004 romantic comedy): 2 wds. |
| 41% | ENCINOMAN | 9 | 1992 comedy featuring 15- and 34-Across: 2 wds. |
| 40% | PRETTYWOMAN | 11 | 1990 Julia Roberts/Richard Gere romantic comedy, with music from 31-Across' opera "La Traviata": 2 wds. |
| 40% | THELOSTCITY | 11 | Romantic adventure comedy starring 15-Across, 43-Across, and Daniel Radcliffe (3 wds.) |
| 39% | EASYA | 5 | 2010 Emma Stone comedy: 2 wds. |
| 38% | THEUGLYTRUTH | 12 | 2009 Gerard Butler romantic comedy that costarred Katherine Heigl: 3 wds. |
| 38% | RUNAWAYBRIDE | 12 | 1999 romantic comedy starring Julia Roberts and Richard Gere: 2 wds. |
| 38% | PALMSPRINGS | 11 | Hulu romantic comedy about a California wedding weekend gone wrong: 2 wds. |
| 38% | KENNYCHESNEY | 12 | Country star with the 2010 hit single "Somewhere With You": 2 wds. |
| 37% | KEVINCOSTNER | 12 | Rene Russo's costar in the 1996 romantic comedy "Tin Cup": 2 wds. |
| 37% | LARRYCROWNE | 11 | Title role played by Tom Hanks in a 2011 romantic comedy: 2 wds. |
| 37% | ROMANHOLIDAY | 12 | 1953 American romantic comedy film starring Audrey Hepburn as Princess Ann: 2 wds. |
| 37% | ALOT | 4 | "___ Like Love," a 2005 romantic comedy starring Ashton Kutcher and Amanda Peet: 2 wds. |
| 37% | GOTMAIL | 7 | "You've ___," 1998 romantic comedy film starring Tom Hanks and Meg Ryan: 2 wds. |
| 37% | PRETTYWOMAN | 11 | 1990 romantic comedy for which Julia Roberts was nominated for an Oscar: 2 wds. |
| 37% | LOVEACTUALLY | 12 | 2003 holiday romantic comedy with Martin Freeman as a stand-in actor: 2 wds. |
| 36% | MODERNTIMES | 11 | 1936 comedy starring 15-/49-Across as a factory worker struggling in the industrialized world: 2 wds. |
| 36% | ADAMSANDLER | 11 | Jennifer Aniston's costar in the 2011 romantic comedy "Just Go With It": 2 wds. |
| 36% | VINCEVAUGHN | 11 | Jennifer Aniston's costar in the 2006 romantic comedy/drama "The Break-Up": 2 wds. |
| 36% | ELLAENCHANTED | 13 | 52-Across plays a giantess in this 2004 romantic comedy starring Anne Hathaway: 2 wds. |
| 36% | ITHAD | 5 | "___ To Be You," a 2015 romantic comedy starring Cristin Milioti and Dan Soder: 2 wds. |
| 36% | MOULINROUGE | 11 | Actor Ewan McGregor's successful musical romantic comedy film directed by Baz Luhrmann: 2 wds. |
| 36% | THEAPARTMENT | 12 | 1960 romantic comedy in which Jack Lemmon played Bud Baxter opposite Shirley MacLaine: 2 wds. |