| 100% | ROSE | 4 | Jack and ___, star-crossed lovers portrayed by Leonardo DiCaprio and Kate Winslet in 1997's "Titanic" |
| 52% | TITANIC | 7 | 1997 film drama starring Leonardo DiCaprio and Kate Winslet |
| 50% | TITANIC | 7 | 1997 shipwreck saga starring Kate Winslet and Leonardo DiCaprio that has been re-released in theaters multiple times |
| 50% | TITANIC | 7 | 1997 epic romance film starring Kate Winslet and Leonardo DiCaprio about the real-life ship that sank in 1912 |
| 47% | TITANIC | 7 | 1997 drama starring Kate Winslet and Leonardo DiCaprio |
| 47% | ANGEL | 5 | Buffy and ___, star-crossed lovers portrayed by Sarah Gellar and David Boreanaz in "Buffy the Vampire Slayer" |
| 42% | KATE | 4 | ___ Winslet and Leonardo Dicaprio, "Titanic" actors who have starred in multiple rom-coms together |
| 37% | ISMAY | 5 | J Bruce —, chairman of the White Star Line shipping company portrayed on screen by Jonathan Hyde in 1997 film Titanic |
| 37% | ROSE | 4 | Character portrayed by Kate Winslet in "Titanic" |
| 34% | ONCEUPONATIME | 13 | "___ in Hollywood," 2019 drama film starring Leonardo DiCaprio and Brad Pitt: 4 wds. |
| 34% | THISBE | 6 | Pyramus and ___, star-crossed lovers featured in Ovid's "Metamorphoses" |
| 33% | IDASTRAUS | 9 | Wife of a co-owner of Macy’s department store, New York, portrayed on screen by Elsa Raven in 1997 film Titanic |
| 33% | THEDEPARTED | 11 | Leonardo DiCaprio movie also starring Jack Nicholson and Matt Damon: 2 wds |
| 32% | TOMHARDY | 8 | Leonardo DiCaprio's "The Revenant" co-star who also starred in 15-Across, 19-Across, 28-Across, and 42-Across (2 wds.) |
| 32% | AVA | 3 | Classic film star Gardner portrayed by Kate Beckinsale in "The Aviator" |
| 32% | HOLLYWOOD | 9 | "Once Upon a Time in ___," 2019 comedy-drama film starring Brad Pitt and Leonardo DiCaprio about Hollywood's "golden age" |
| 32% | JEDGARHOOVER | 12 | Real-life FBI director and title character played by Leonardo DiCaprio in a 2011 film: 3 wds. |
| 32% | TITANIC | 7 | 1997 Kate Winslet/Leonardo DiCaprio blockbuster |
| 32% | CONTAGION | 9 | Medical thriller film directed by Steven Soderbergh starring Kate Winslet and Matt Damon |
| 31% | ROSE | 4 | Kate Winslet's role in "The Titanic" |
| 31% | TITANIC | 7 | 1997 film starring Leonardo DiCaprio that was inspired by a real-life disaster involving an "unsinkable" ship |
| 31% | IRIS | 4 | Novelist Murdoch who was played by Kate Winslet and Judi Dench in a 2001 biopic |
| 31% | OPHELIA | 7 | Noblewoman played by Helena Bonham Carter, Kate Winslet, and Daisy Ridley in film versions of a Shakespeare play |
| 30% | ROSE | 4 | Kate Winslet in "The Titanic" |
| 30% | PHRENOLOGIST | 12 | Practitioner of the racist pseudoscience espoused by Leonardo DiCaprio’s character in “Django Unchained” |
| 29% | ARROW | 5 | Projectile used by Clint Barton and Kate Bishop in "Hawkeye" |
| 29% | FOOTBRIDGE | 10 | Stream crossing for pedestrians ... and what is literally provided by the interior letters in the answers to starred clues |
| 29% | ROSE | 4 | Kate Winslet's role in "Titanic" |
| 29% | HOWARDHUGHES | 12 | Real-life business magnate played by Leonardo DiCaprio in 2004's "The Aviator": 2 wds. |
| 29% | CATEBLANCHETT | 13 | "Thor: Ragnarok" actress and co-star of Leonardo DiCaprio in "The Aviator" (2 wds.) |