| 100% | DRUGS | 5 | "Love & Other ___," romantic comedy-drama movie starring Jake Gyllenhaal and Anne Hathaway |
| 66% | LOVE | 4 | "___ & Other Drugs," 2010 romantic comedy film starring Anne Hathaway and Jake Gyllenhaal |
| 49% | WARS | 4 | "Bride ___," 2009 romantic comedy film starring Anne Hathaway and Kate Hudson |
| 45% | YORK | 4 | "New ___, I Love You," romantic comedy-drama movie starring Bradley Cooper and Natalie Portman |
| 43% | BROTHERS | 8 | 2009 drama starring Jake Gyllenhaal and Natalie Portman |
| 42% | BECOMINGJANE | 12 | 2007 biographical romantic drama starring Anne Hathaway and James McAvoy: 2 wds. |
| 42% | SOUTHPAW | 8 | 2015 film drama starring Jake Gyllenhaal and Forest Whitaker |
| 42% | DONNIEDARKO | 11 | 2001 film drama starring Jake Gyllenhaal and Jena Malone |
| 42% | MOONLIGHT | 9 | 2002 film drama starring Jake Gyllenhaal and Dustin Hoffman |
| 40% | OCTOBER | 7 | & 12D 1999 film drama starring Jake Gyllenhaal and Chris Cooper |
| 39% | GET | 3 | 2008 film comedy starring Steve Carell and Anne Hathaway |
| 39% | MODERN | 6 | "___ Love," Amazon Prime Video romantic comedy series starring Tina Fey and Dev Patel among others |
| 39% | ELLAENCHANTED | 13 | 52-Across plays a giantess in this 2004 romantic comedy starring Anne Hathaway: 2 wds. |
| 39% | DRUNK | 5 | "Punch-___ Love," dark romantic comedy-drama starring Adam Sandler and Emily Watson |
| 38% | THEGOOD | 7 | & 15A 2002 comedy-drama film starring Jennifer Aniston and Jake Gyllenhaal |
| 38% | RACHEL | 6 | 2008 drama starring Anne Hathaway and Rosemarie DeWitt |
| 37% | GET | 3 | & 18D 2008 film comedy starring Steve Carell and Anne Hathaway |
| 37% | LOL | 3 | 2012 romantic drama movie that starred Miley Cyrus and Demi Moore |
| 37% | RENDITION | 9 | 2007 film thriller starring Jake Gyllenhaal and Reese Witherspoon |
| 37% | JARHEAD | 7 | 2005 war film starring Jake Gyllenhaal and Peter Sarsgaard |
| 37% | SOURCECODE | 10 | 2011 film thriller starring Jake Gyllenhaal and Michelle Monaghan |
| 37% | PINK | 4 | "Pretty in ___," 1986 romantic comedy-drama starring Molly Ringwald and Kristy Swanson |
| 37% | DON | 3 | "___ Jon," a 2013 romantic comedy-drama starring Joseph Gordon-Levitt and Scarlett Johansson |
| 36% | SUNSHINE | 8 | "___ Cleaning," 2008 comedy drama movie starring Emily Blunt as Norah Lorkowski |
| 36% | HAVOC | 5 | 2005 film drama starring Anne Hathaway and Bijou Phillips |
| 36% | GET | 3 | Steve Carell and Anne Hathaway starrer "___ Smart" |