| 100% | GANGSOF | 7 | & 21A 2002 drama film starring Leonardo DiCaprio, Daniel Day-Lewis and Cameron Diaz |
| 55% | OFNEWYORK | 9 | "Gangs ___," 2002 epic period drama film starring Cameron Diaz and Leonardo DiCaprio: 3 wds. |
| 45% | ONCEUPONATIME | 13 | "___ in Hollywood," 2019 drama film starring Leonardo DiCaprio and Brad Pitt: 4 wds. |
| 42% | ANY | 3 | "___ Given Sunday," 1999 sports drama film starring Cameron Diaz and Al Pacino |
| 40% | TITANIC | 7 | 1997 film drama starring Leonardo DiCaprio and Kate Winslet |
| 40% | BLOODDIAMOND | 12 | 2006 film drama starring Leonardo DiCaprio and Djimon Hounsou |
| 39% | BOXER | 5 | The —, 1997 film drama starring Daniel Day-Lewis and Emily Watson |
| 38% | BODYOFLIES | 10 | 2008 action film starring Leonardo DiCaprio and Russell Crowe |
| 38% | THEREVENANT | 11 | 2015 adventure film starring Leonardo DiCaprio and Tom Hardy |
| 38% | ROMEO | 5 | "___ + Juliet" (Baz Luhrmann film starring Leonardo DiCaprio and Claire Danes) |
| 37% | INCEPTION | 9 | 2010 sci-fi film starring Leonardo DiCaprio and Joseph Gordon-Levitt |
| 36% | LAYERCAKE | 9 | 2004 crime drama film starring Daniel Craig and Colm Meaney |
| 36% | SHUTTERISLAND | 13 | Dennis Lehane novel made into a film starring Leonardo DiCaprio and Mark Ruffalo (2 wds.) |
| 35% | MYSISTERS | 9 | & 10A 2009 film drama starring Cameron Diaz and Abigail Breslin |
| 35% | GANGSOFNEWYORK | 14 | 2002 drama starring Daniel Day-Lewis that did not win any Oscars despite 10 nominations: 4 wds. |
| 35% | HOLLYWOOD | 9 | "Once Upon a Time in ___," 2019 comedy-drama film starring Brad Pitt and Leonardo DiCaprio about Hollywood's "golden age" |
| 35% | THEBOX | 6 | 2009 mystery film starring Cameron Diaz and James Marsden |
| 34% | BOX | 3 | The —, 2009 film drama starring Cameron Diaz and James Marsden |
| 34% | BOX | 3 | The —, 2009 mystery film starring Cameron Diaz and James Marsden |
| 34% | BAD | 3 | "___ Teacher," 2011 romantic comedy film starring Cameron Diaz and Jason Segel |
| 34% | MAX | 3 | 2002 film drama starring John Cusack and Noah Taylor |
| 34% | UNFAITHFUL | 10 | 2002 film drama starring Richard Gere and Diane Lane |
| 34% | MOONLIGHT | 9 | 2002 film drama starring Jake Gyllenhaal and Dustin Hoffman |
| 33% | HOLIDAY | 7 | "The ___," 2006 American romantic comedy film starring Cameron Diaz and Kate Winslet |
| 33% | WHAT | 4 | "___ Happens in Vegas," 2008 romantic comedy film starring Cameron Diaz and Ashton Kutcher |
| 33% | HEAVENS | 7 | & 21A 1980 film drama starring Kris Kristofferson and Christopher Walken |