| MATRIX | The _, 1999 Keanu Reeves fill |
| THEMATRIX | 1999 Keanu Reeves blockbuster: 2 wds. |
| OCEAN | "The Deep End of the ___" (1999) |
| MOON | "Man on the ___" (1999) |
| KINGSEVIL | The ___, 1999 novel by Edward Marston (5,4) |
| LIAR | "Jakob the ___"; 1999 film for Robin Williams |
| ALIBI | The ___, 1999 novel by Sandra Brown (5) |
| PJS | "The ___"; 1999-2001 primetime animated series |
| INSIDER | The ___ , 1999 film starring Al Pacino (7) |
| MUMMY | The _, 1999 action horror flick set in Egypt (5) |
| LONGFIRM | The ___, 1999 novel by Jake Arnott (4,4) |
| MUSE | The ___ (1999 Sharon Stone movie) |
| BACHELOR | The ___, 1999 romcom starring Chris O'Donnell and Renee Zellweger (8) |
| GREEN | The ___, 1999 film drama starring Tom Hanks and Michael Clarke Duncan (5,4) |
| IRON | The ___, 1999 animated film based on a book by Ted Hughes (4,5) |
| SIXTHSENSE | The ___, 1999 mystery film starring Bruce Willis and Haley Joel Osment (5,5) |
| HURRICANE | The ___, 1999 biopic starring Denzel Washington as boxer Rubin Carter (9) |
| CIDERHOUSERULES | The ____ , 1999 film based on a novel by U.S. author John Irving for which Michael Caine won his second acting Oscar (5,5,5) |
| PRIORY | The ___, 1999-2001 TV show of celebrity chat and games presented by Zoe Ball and Jamie Theakston (6) |
| IHATE | 10 __, 1999 movie based on The Taming of the Shrew (6,1,4,5,3) |
