| 100% | NINEMONTHS | 10 | 1995 romcom starring Hugh Grant and 29-Across (2 wds.) |
| 78% | NINEMONTHS | 10 | 1995 rom-com starring Hugh Grant and 29-Across (2 wds.) |
| 67% | NINEMONTHS | 10 | "Odd" 1995 film starring Hugh Grant and Julianne Moore: 2 wds. |
| 66% | NINEMONTHS | 10 | 1995 romcom starring Hugh Grant and Julianne Moore |
| 53% | MUSIC | 5 | & 2D 2007 romcom starring Hugh Grant and Drew Barrymore |
| 47% | STILLALICE | 10 | 2014 drama starring Alec Baldwin and 29-Across (2 wds.) |
| 46% | LASTCHRISTMAS | 13 | Holiday romcom starring 18-Across and 38-Across and featuring songs by George Michael and Wham! (2 wds.) |
| 45% | BRIDGET | 7 | & 9D 2001 romcom starring Renee Zellweger, Colin Firth and Hugh Grant |
| 44% | LORNEMICHAELS | 13 | Seth Meyers' executive producer on 24- and 29-Across: 2 wds. |
| 43% | THEPRESTIGE | 11 | Thriller starring Hugh Jackman and Christian Bale as competing magicians (2 wds.) |
| 43% | ELLAENCHANTED | 13 | Fantasy comedy film starring Hugh Dancy and 44-Across as characters based on a fairy tale (2 wds.) |
| 43% | THEPROPOSAL | 11 | Romcom starring Ryan Reynolds and Sandra Bullock which grossed $317 million worldwide in 2009: 2 wds. |
| 43% | PRETTYWOMAN | 11 | Romcom starring Richard Gere and Julia Roberts which grossed $463 million worldwide in 1990: 2 wds. |
| 42% | TWOWEEKS | 8 | & 1D 2002 romcom starring Sandra Bullock and Hugh Grant |
| 42% | GETSHORTY | 9 | 1995 comedy film starring 17-Across and 30-Across based on an Elmore Leonard novel (2 wds.) |
| 41% | SILKSONIC | 9 | "Leave the Door Open" R&B super-duo formed by 16- and 29-Across: 2 wds. |
| 41% | REALSTEEL | 9 | Science fiction sports film starring Hugh Jackman and Evangeline Lilly: 2 wds. |
| 41% | TRIPLECROWN | 11 | Batting feat that 17- and 29-Across achieved twice each: 2 wds. |
| 41% | ABOY | 4 | "About ___ " (2002 Hugh Grant movie): 2 wds. |
| 41% | HILL | 4 | "Notting ___," 1999 romantic comedy film starring Hugh Grant and Julia Roberts |
| 40% | DIARY | 5 | "Bridget Jones's ___," romantic comedy film starring Hugh Grant and Renee Zellweger |
| 40% | FOURWEDDINGS | 12 | 16A & 21A 1994 comedy-drama film starring Hugh Grant and Andie MacDowell |
| 40% | LOVE | 4 | "___ Actually," 2003 Christmas-themed rom-com starring Hugh Grant and Emma Thompson |
| 40% | MRHOLLANDSOPUS | 14 | 1995 drama starring Richard Dreyfuss, Glenne Headly, and 52-Across (3 wds.) |
| 40% | KNOCKEDUP | 9 | Comedy starring Seth Rogen and 47-Across (2 wds.) |
| 40% | ITTAKESTWO | 10 | 1995 romcom starring Kirstie Alley and Steve Guttenberg |
| 40% | MARKWAHLBERG | 12 | "The Lovely Bones," 14-Across, and 29-Across star who turns 50 years old tomorrow (2 wds.) |
| 40% | ABOY | 4 | Hugh Grant film "About ___" (2 wds.) |
| 39% | CHARLIZETHERON | 14 | 15-Across and 29-Across star who won a Best Actress Oscar for "Monster" and who turns 45 today (2 wds.) |
| 39% | THERESIDENT | 11 | Medical drama starring 17-Across and 28-Across (2 wds.) |