1999 in film Highest-grossing films Highest-grossing films of 1999

| Rank_ | Title | Studio | Directors | Worldwide_Gross |
|---|---|---|---|---|
| 10. | Austin Powers: The Spy Who Shagged Me | New Line Cinema | Jay Roach | $312,016,858 |
| 11. | Runaway Bride | Paramount / Touchstone | Garry Marshall | $309,457,509 |
| 12. | Stuart Little | Columbia Pictures | Rob Minkoff | $300,135,367 |
| 13. | The Green Mile | Warner Bros. | Frank Darabont | $290,701,374 |
| 14. | The Blair Witch Project | Haxan Films | Eduardo Sánchez and Daniel Myrick | $248,639,099 |
| 15. | American Pie | Universal Studios | Paul Weitz | $235,483,004 |
| 16. | Big Daddy | Columbia Pictures | Dennis Dugan | $234,801,895 |
| 17. | Wild Wild West | Warner Bros. | Barry Sonnenfeld | $222,105,681 |
| 18. | Entrapment | 20th Century Fox | Jon Amiel | $212,404,396 |
| 19. | End of Days | Universal Studios | Peter Hyams | $211,989,043 |
| 20. | Sleepy Hollow | Paramount Pictures | Tim Burton | $206,071,502 |