| 100% | LALALAND | 8 | 2016 movie musical starring Ryan Gosling and 43-Across (3 wds.) |
| 55% | LALALAND | 8 | 2016 romantic musical starring 13-Across and Emma Stone: 3 wds. |
| 52% | LALA | 4 | "___ Land," 2016 musical starring Emma Stone and Ryan Gosling: 2 wds. |
| 48% | LALA | 4 | "___ Land," 2016 musical Starring Ryan Gosling: 2 wds. |
| 47% | LALA | 4 | "___ Land" (2016 film starring Ryan Gosling and Emma Stone) (2 wds.) |
| 47% | LALA | 4 | "___ Land," movie starring Ryan Gosling and Emma Stone: 2 wds. |
| 45% | LALALAND | 8 | 2016 movie musical whose songs' lyrics were written by the same composing team as 16-Across: 3 wds. |
| 44% | LALA | 4 | "___ Land", musical drama film starring Ryan Gosling and Emma Stone: 2 wds. |
| 43% | BLUEVALENTINE | 13 | 2010 romantic drama starring Ryan Gosling and Michelle Williams: 2 wds. |
| 43% | GANGSTERSQUAD | 13 | 2013 crime film starring Ryan Gosling and Emma Stone: 2 wds. |
| 42% | DRIVE | 5 | 2011 heist movie starring Ryan Gosling and Carey Mulligan |
| 41% | THENICEGUYS | 11 | A 2016 comedy starring Crowe and Gosling: 3 wds |
| 39% | LALALAND | 8 | 2016 movie musical nominated for a record-tying 14 Oscars (3 wds.) |
| 38% | LALA | 4 | "___ Land," a 2016 film starring Emma Stone and Ryan Gosling: 2 wds. |
| 37% | HALFNELSON | 10 | 2006 film drama starring Ryan Gosling and Shareeka Epps |
| 37% | NOTEBOOK | 8 | The —, 2004 film drama starring Ryan Gosling and James Garner |
| 37% | LALA | 4 | "___ Land" (2016 Ryan Gosling movie): 2 wds. |
| 36% | HEGOTGAME | 9 | 1998 basketball movie starring Denzel Washington and Ray Allen: 3 wds. |
| 36% | DOCTORSTRANGE | 13 | 2016 superhero film starring Benedict Cumberbatch and 47-Across (2 wds.) |
| 36% | LALA | 4 | "___ Land" (A musical rom-com starring Emma Stone and Ryan Gosling): 2 wds. |
| 36% | EVITA | 5 | 1996 movie musical starring Madonna and Antonio Banderas |
| 36% | LALA | 4 | Ryan Gosling starrer "___ Land": 2 wds. |
| 35% | BLACKSWAN | 9 | Ballet film starring Natalie Portman and 43-Across (2 wds.) |
| 35% | BLOODTIES | 9 | Crime film starring Clive Owen and 43-Across (2 wds.) |
| 35% | THEJUNGLEBOOK | 13 | 2016 kids' movie starring Idris Elba: 3 wds. |
| 34% | ARIANAGRANDE | 12 | Pop singer and former Nickelodeon star who both hosted "SNL" and performed as the musical guest in 2016: 2 wds. |
| 34% | CABARET | 7 | Movie musical that starred Liza Minnelli and Joel Grey |
| 34% | BABESINARMS | 11 | 1939 movie musical costarring Mickey Rooney: 3 wds. |
| 34% | THENOTEBOOK | 11 | Nicholas Sparks novel made into a film starring Ryan Gosling and Rachel McAdams (2 wds.) |
| 34% | QUEENOFKATWE | 12 | 2016 biopic about an African chess master starring Lupita Nyong'o and 45-Across (3 wds.) |