This is a list of films which have placed number one at the weekend box office in the United States during 1999.
| # | Weekend End Date | Film | Box Office | Notes |
|---|---|---|---|---|
| 1 | 01999-01-03 January 3, 1999 | Patch Adams | $19,050,675 | |
| 2 | 01999-01-10 January 10, 1999 | A Civil Action | $15,163,484 | |
| 3 | 01999-01-17 January 17, 1999 | Varsity Blues | $15,204,148 | |
| 4 | 01999-01-24 January 24, 1999 | Varsity Blues | $10,574,508 | |
| 5 | 01999-01-31 January 31, 1999 | She's All That | $16,065,430 | |
| 6 | 01999-02-07 February 7, 1999 | Payback | $21,221,526 | |
| 7 | 01999-02-14 February 14, 1999 | Message in a Bottle | $18,852,976 | |
| 8 | 01999-02-21 February 21, 1999 | Payback | $10,268,237 | |
| 9 | 01999-02-28 February 28, 1999 | 8mm | $14,252,888 | |
| 10 | 01999-03-07 March 7, 1999 | Analyze This | $18,383,507 | |
| 11 | 01999-03-14 March 14, 1999 | Analyze This | $15,567,669 | |
| 12 | 01999-03-21 March 21, 1999 | Forces of Nature | $13,510,728 | |
| 13 | 01999-03-28 March 28, 1999 | Forces of Nature | $9,439,629 | |
| 14 | 01999-04-04 April 4, 1999 | The Matrix | $27,788,331 | The Matrix broke Lost in Space's record ($20.2 mil) for the highest weekend debut in April. |
| 15 | 01999-04-11 April 11, 1999 | The Matrix | $22,563,331 | |
| 16 | 01999-04-18 April 18, 1999 | Life | $20,414,775 | |
| 17 | 01999-04-25 April 25, 1999 | The Matrix | $12,642,717 | |
| 18 | 01999-05-02 May 2, 1999 | Entrapment | $20,145,595 | |
| 19 | 01999-05-09 May 9, 1999 | The Mummy | $43,369,635 | |
| 20 | 01999-05-16 May 16, 1999 | The Mummy | $24,856,320 | |
| 21 | 01999-05-23 May 23, 1999 | Star Wars Episode I: The Phantom Menace | $64,820,970 | Star Wars Episode I: The Phantom Menace had the highest weekend debut in 1999. |
| 22 | 01999-05-30 May 30, 1999 | Star Wars Episode I: The Phantom Menace | $51,399,863 | Star Wars Episode I: The Phantom Menace broke Jurassic Park's record ($38.5 mil) for the highest 2nd weekend gross. |
| 23 | 01999-06-06 June 6, 1999 | Star Wars Episode I: The Phantom Menace | $32,891,653 | |
| 24 | 01999-06-13 June 13, 1999 | Austin Powers: The Spy Who Shagged Me | $54,917,604 | Austin Powers: The Spy Who Shagged Me broke Batman Forever's record ($52.8 mil) for the highest weekend in June. |
| 25 | 01999-06-20 June 20, 1999 | Tarzan | $34,221,968 | |
| 26 | 01999-06-27 June 27, 1999 | Big Daddy | $41,536,370 | |
| 27 | 01999-07-04 July 4, 1999 | Wild Wild West | $27,687,484 | |
| 28 | 01999-07-11 July 11, 1999 | American Pie | $18,709,680 | |
| 29 | 01999-07-18 July 18, 1999 | Eyes Wide Shut | $21,706,163 | |
| 30 | 01999-07-25 July 25, 1999 | The Haunting | $33,435,140 | |
| 31 | 01999-08-01 August 1, 1999 | Runaway Bride | $35,055,556 | |
| 32 | 01999-08-08 August 8, 1999 | The Sixth Sense | $26,681,262 | The Sixth Sense broke The Fugitive's record ($23.8 mil) for the highest weekend debut in August. |
| 33 | 01999-08-15 August 15, 1999 | The Sixth Sense | $25,764,991 | |
| 34 | 01999-08-22 August 22, 1999 | The Sixth Sense | $23,950,008 | |
| 35 | 01999-08-29 August 29, 1999 | The Sixth Sense | $20,099,149 | |
| 36 | 01999-09-05 September 5, 1999 | The Sixth Sense | $22,896,967 | The Sixth Sense broke The Fugitive's record ($17.2 mil) for the highest Labor Day weekend ever. |
| 37 | 01999-09-12 September 12, 1999 | Stigmata | $18,309,666 | |
| 38 | 01999-09-19 September 19, 1999 | Blue Streak | $19,208,806 | |
| 39 | 01999-09-26 September 26, 1999 | Double Jeopardy | $23,162,542 | |
| 40 | 01999-10-03 October 3, 1999 | Double Jeopardy | $17,018,808 | |
| 41 | 01999-10-10 October 10, 1999 | Double Jeopardy | $13,541,285 | |
| 42 | 01999-10-17 October 17, 1999 | Fight Club | $11,035,485 | |
| 43 | 01999-10-24 October 24, 1999 | The Best Man | $9,031,660 | |
| 44 | 01999-10-31 October 31, 1999 | House on Haunted Hill | $15,946,032 | |
| 45 | 01999-11-07 November 7, 1999 | The Bone Collector | $16,712,020 | |
| 46 | 01999-11-14 November 14, 1999 | Pokémon: The First Movie | $31,036,678 | |
| 47 | 01999-11-21 November 21, 1999 | The World Is Not Enough | $35,519,007 | |
| 48 | 01999-11-28 November 28, 1999 | Toy Story 2 | $57,388,839 | Toy Story 2 broke The Waterboy's record ($39.4 mil) for the highest weekend debut in November, 101 Dalmatians's record ($33.5 mil) for the highest Thanksgiving weekend debut, and The Lion King's record ($40.9 mil) for the highest weekend debut for an animated film. |
| 49 | 01999-12-05 December 5, 1999 | Toy Story 2 | $27,760,276 | |
| 50 | 01999-12-12 December 12, 1999 | Toy Story 2 | $18,249,880 | |
| 51 | 01999-12-19 December 19, 1999 | Stuart Little | $15,018,223 | |
| 52 | 01999-12-26 December 26, 1999 | Any Given Sunday | $13,584,625 | |
| 53 | 02000-01-02 January 2, 2000 | Stuart Little | $16,022,757 |
| Preceded by Box office number-one films of 1998 (USA) |
Box office number-one films of 1999 (USA) 1999 |
Succeeded by Box office number-one films of 2000 (USA) |
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