| pos. | Title | Gross | |
|---|---|---|---|
| 1 |  | Star Wars Episode I: The Phantom Menace (1999) | $427,607,869 |
| 2 |  | The Sixth Sense (1999) | $259,835,832 |
| 3 |  | Austin Powers: The Spy Who Shagged Me (1999) | $205,399,422 |
| 4 |  | Tarzan (1999) | $170,445,708 |
| 5 |  | Big Daddy (1999) | $163,479,795 |
| 6 |  | The Mummy (1999) | $155,247,825 |
| 7 |  | Runaway Bride (1999) | $150,006,531 |
| 8 |  | The Blair Witch Project (1999) | $140,413,654 |
| 9 |  | The Matrix (1999) | $120,636,167 |
| 10 |  | Notting Hill (1999) | $116,087,037 |
| 11 |  | The Generals Daughter (1999) | $102,678,089 |
| 12 |  | American Pie (1999) | $101,736,215 |
| 13 |  | Wild Wild West (1999) | $100,424,973 |
| 14 |  | Double Jeopardy (2000) | $98,301,710 |
| 15 |  | Inspector Gadget (1999) | $96,239,370 |
| 16 |  | Analyze This (1999) | $94,340,129 |
| 17 |  | The Haunting (1999) | $91,307,903 |
| 18 |  | Entrapment (1999) | $76,202,389 |
| 19 |  | The Thomas Crown Affair (1999) | $68,552,907 |
| 20 |  | Deep Blue Sea (1999) | $67,090,354 |