| 100% | RIPLEY | 6 | "The Talented Mr. ___" (1999 movie) |
| 100% | RIPLEY | 6 | "The Talented Mr. ___," 1999 movie starring Gwyneth Paltrow as Marge Sherwood |
| 75% | RIPLEY | 6 | "The Talented Mr. ___," 1999 film starring Philip Seymour Hoffman and Matt Damon |
| 69% | HIGHSMITH | 9 | Patricia who wrote The Talented Mr. Ripley |
| 66% | MATRIX | 6 | 1999 movie with Neo and Morpheus, The __ |
| 64% | MAGNOLIA | 8 | 1999 movie inspired by the songs of Aimee Mann |
| 62% | RIPLEY | 6 | “The Talented Mr. —” |
| 59% | NEO | 3 | Mr. Anderson's other name in the "Matrix" movies |
| 59% | OAR | 3 | "The Talented Mr. Ripley" murder weapon |
| 59% | LAW | 3 | "The Talented Mr. Ripley" actor Jude |
| 59% | MATT | 4 | "The Talented Mr. Ripley" star Damon |
| 58% | TIMBUKTU | 8 | 1999 novella by Paul Auster about Mr Bones the dog |
| 58% | RIPLEY | 6 | "The Talented Mr. ___," film starring Matt Damon |
| 57% | MIYAGI | 6 | Pat Morita, Mr. __ in The Karate Kid movies |
| 57% | DAMON | 5 | Matt of "The Talented Mr. Ripley" |
| 57% | TIMBUKTU | 8 | 1999 short novel by Paul Auster about Mr Bones the dog |
| 57% | TARZAN | 6 | 1999 animated movie starring Minnie Driver as the voice of Jane |
| 56% | LAW | 3 | Actor Jude of "The Talented Mr. Ripley" |
| 56% | OAR | 3 | Murder weapon in "The Talented Mr. Ripley" |
| 56% | ITALY | 5 | European setting of "The Talented Mr. Ripley" |
| 55% | MATT | 4 | Tom’s portrayer in “The Talented Mr. Ripley” |
| 52% | THEMATRIX | 9 | 1999 sci-fi action movie added to the National Film Registry in 2012: 2 wds |
| 52% | ROSIE | 5 | O'Donnell who voiced Tarzan's gorilla friend in the 1999 Disney movie |
| 52% | JUDELAW | 7 | Actor in "A.I. Artificial Intelligence" and "The Talented Mr. Ripley" |
| 51% | FIGHTCLUB | 9 | 1999 Brad Pitt movie hinted at by the beginnings of 17-, 21-, 39- and 52-Across |
| 50% | ARNOLD | 6 | Muscular actor and former Mr. Olympia, ___ Schwarzenegger who has starred in the movie "The Terminator" |
| 50% | GEORGE | 6 | "Curious ___," 2006 animated movie which features the voice of Dick Van Dyke as Mr. Bloomsberry |
| 48% | PARIS | 5 | "Passport to ___," 1999 direct-to-video movie starring the Olsen twins which is set in France |
| 48% | OAR | 3 | Boating implement that was used as a murder weapon in "The Talented Mr. Ripley" |
| 48% | DRIVEMECRAZY | 12 | 1999 Melissa Joan Hart movie |