| Rank
| Release
| Genre
| Budget
| Running Time
| Gross | Max Theaters | Total Gross | % of Total | Release Date | Distributor
|
|---|
| 1 | Stuart Little | - | - | - | $19,083,299 | 3,151 | $140,035,367 | 13.6% | Dec 17, 1999 | Sony Pictures Releasing |
| 2 | The Green Mile | - | - | - | $18,006,303 | 2,875 | $136,801,374 | 13.2% | Dec 10, 1999 | Warner Bros. |
| 3 | The Talented Mr. Ripley | - | - | - | $16,023,319 | 2,369 | $81,298,265 | 19.7% | Dec 25, 1999 | Paramount Pictures |
| 4 | Next Friday | - | - | - | $14,522,230 | 1,420 | $57,328,603 | 25.3% | Jan 12, 2000 | New Line Cinema |
| 5 | Galaxy Quest | - | - | - | $14,387,218 | 2,450 | $71,583,916 | 20.1% | Dec 25, 1999 | DreamWorks Distribution |
| 6 | Any Given Sunday | - | - | - | $14,368,011 | 2,505 | $75,530,832 | 19% | Dec 22, 1999 | Warner Bros. |
| 7 | Toy Story 2 | - | - | - | $11,747,547 | 3,257 | $245,852,179 | 4.8% | Nov 19, 1999 | Walt Disney Studios Motion Pictures |
| 8 | Magnolia | - | - | - | $9,854,087 | 1,086 | $22,455,976 | 43.9% | Dec 17, 1999 | New Line Cinema |
| 9 | The Hurricane | - | - | - | $9,683,395 | 2,148 | $50,699,241 | 19.1% | Dec 29, 1999 | Universal Pictures |
| 10 | Bicentennial Man | - | - | - | $7,585,396 | 2,767 | $58,223,861 | 13% | Dec 17, 1999 | Walt Disney Studios Motion Pictures |
| 11 | Deuce Bigalow: Male Gigolo | - | - | - | $7,517,466 | 2,162 | $65,538,755 | 11.5% | Dec 10, 1999 | Walt Disney Studios Motion Pictures |
| 12 | Snow Falling on Cedars | - | - | - | $6,965,575 | 1,155 | $14,417,593 | 48.3% | Dec 22, 1999 | Universal Pictures |
| 13 | Girl, Interrupted | - | - | - | $5,897,907 | 1,935 | $28,912,646 | 20.4% | Dec 21, 1999 | Sony Pictures Releasing |
| 14 | Anna and the King | - | - | - | $5,651,772 | 2,132 | $39,263,420 | 14.4% | Dec 17, 1999 | Twentieth Century Fox |
| 15 | The Cider House Rules | - | - | - | $5,270,790 | 1,738 | $57,545,092 | 9.2% | Dec 10, 1999 | Miramax |
| 16 | Man on the Moon | - | - | - | $5,198,405 | 2,079 | $34,607,430 | 15% | Dec 22, 1999 | Universal Pictures |
| 17 | Fantasia 2000 | - | - | - | $4,688,166 | 1,313 | $60,655,420 | 7.7% | Jan 1, 2000 | Walt Disney Studios Motion Pictures |
| 18 | The World Is Not Enough | - | - | - | $2,846,097 | 3,163 | $126,943,684 | 2.2% | Nov 19, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 19 | Supernova | - | - | - | $2,188,118 | 2,280 | $14,230,455 | 15.4% | Jan 14, 2000 | Metro-Goldwyn-Mayer (MGM) |
| 20 | Sleepy Hollow | - | - | - | $1,760,453 | 3,069 | $101,071,502 | 1.7% | Nov 19, 1999 | Paramount Pictures |
| 21 | End of Days | - | - | - | $1,278,417 | 2,652 | $66,889,043 | 1.9% | Nov 24, 1999 | Universal Pictures |
| 22 | The End of the Affair | - | - | - | $1,090,267 | 688 | $10,827,816 | 10.1% | Dec 3, 1999 | Sony Pictures Releasing |
| 23 | Being John Malkovich | - | - | - | $861,437 | 630 | $22,863,596 | 3.8% | Oct 29, 1999 | USA Films |
| 24 | American Beauty | - | - | - | $815,210 | 1,990 | $130,096,601 | 0.6% | Sep 15, 1999 | DreamWorks Distribution |
| 25 | The Bone Collector | - | - | - | $688,149 | 2,623 | $66,518,655 | 1% | Nov 5, 1999 | Universal Pictures |
| 26 | All About My Mother | - | - | - | $679,307 | 145 | $8,272,296 | 8.2% | Nov 5, 1999 | Sony Pictures Classics |
| 27 | Mansfield Park | - | - | - | $632,197 | 152 | $4,775,847 | 13.2% | Nov 19, 1999 | Miramax |
| 28 | The Sixth Sense | - | - | - | $590,550 | 2,821 | $293,506,292 | 0.2% | Aug 6, 1999 | Walt Disney Studios Motion Pictures |
| 29 | Three Kings | - | - | - | $551,050 | 2,942 | $60,652,036 | 0.9% | Oct 1, 1999 | Warner Bros. |
| 30 | Dogma | - | - | - | $419,100 | 1,292 | $30,652,890 | 1.4% | Nov 12, 1999 | Lionsgate |
| 31 | Liberty Heights | - | - | - | $404,889 | 115 | $3,736,868 | 10.8% | Nov 19, 1999 | Warner Bros. |
| 32 | Mysteries of Egypt | - | - | - | $366,035 | 27 | $40,593,486 | 0.9% | Aug 21, 1998 | IMAX |
| 33 | Bringing Out the Dead | - | - | - | $315,736 | 1,967 | $16,797,191 | 1.9% | Oct 22, 1999 | Paramount Pictures |
| 34 | The Insider | - | - | - | $291,849 | 1,844 | $29,089,912 | 1% | Nov 5, 1999 | Walt Disney Studios Motion Pictures |
| 35 | The Straight Story | - | - | - | $288,567 | 186 | $6,203,044 | 4.7% | Oct 15, 1999 | Walt Disney Studios Motion Pictures |
| 36 | Pokémon: The First Movie - Mewtwo Strikes Back | - | - | - | $282,664 | 3,043 | $85,744,662 | 0.3% | Nov 10, 1999 | Warner Bros. |
| 37 | Star Wars: Episode I - The Phantom Menace | - | - | - | $279,258 | 3,126 | $431,088,295 | <0.1% | May 19, 1999 | Twentieth Century Fox |
| 38 | Double Jeopardy | - | - | - | $278,106 | 3,002 | $116,741,558 | 0.2% | Sep 24, 1999 | Paramount Pictures |
| 39 | Sweet and Lowdown | - | - | - | $250,791 | 239 | $4,197,015 | 6% | Dec 3, 1999 | Sony Pictures Classics |
| 40 | Cradle Will Rock | - | - | - | $250,046 | 506 | $2,903,404 | 8.6% | Dec 10, 1999 | Walt Disney Studios Motion Pictures |
| 41 | The Best Man | - | - | - | $235,531 | 1,348 | $34,102,780 | 0.7% | Oct 22, 1999 | Universal Pictures |
| 42 | Tumbleweeds | - | - | - | $229,584 | 307 | $1,350,248 | 17% | Nov 26, 1999 | Fine Line Features |
| 43 | Fight Club | - | - | - | $223,396 | 1,966 | $37,030,102 | 0.6% | Oct 15, 1999 | Twentieth Century Fox |
| 44 | Boys Don't Cry | - | - | - | $212,575 | 365 | $11,540,607 | 1.8% | Oct 8, 1999 | Fox Searchlight Pictures |
| 45 | American Movie | - | - | - | $203,072 | 29 | $1,165,795 | 17.4% | Nov 5, 1999 | Sony Pictures Classics |
| 46 | House on Haunted Hill | - | - | - | $174,500 | 2,710 | $40,846,082 | 0.4% | Oct 29, 1999 | Warner Bros. |
| 47 | Runaway Bride | - | - | - | $174,076 | 3,240 | $152,257,509 | 0.1% | Jul 30, 1999 | Paramount Pictures |
| 48 | Superstar | - | - | - | $171,030 | 2,016 | $30,636,478 | 0.6% | Oct 8, 1999 | Paramount Pictures |
| 49 | Anywhere But Here | - | - | - | $170,465 | 1,686 | $18,670,401 | 0.9% | Nov 12, 1999 | Twentieth Century Fox |
| 50 | Island of the Sharks | - | - | - | $162,595 | 17 | $10,658,505 | 1.5% | Apr 23, 1999 | IMAX |
| 51 | Mela | - | - | - | $158,623 | 29 | $220,524 | 71.9% | Jan 7, 2000 | Eros Worldwide |
| 52 | Blue Streak | - | - | - | $154,989 | 2,735 | $68,518,533 | 0.2% | Sep 17, 1999 | Sony Pictures Releasing |
| 53 | Bulandi | - | - | - | $152,798 | 30 | $203,548 | 75.1% | Jan 7, 2000 | Video Sound |
| 54 | The Limey | - | - | - | $138,628 | 105 | $3,204,663 | 4.3% | Oct 8, 1999 | Artisan Entertainment |
| 55 | Angela's Ashes | - | - | - | $123,080 | 614 | $13,042,112 | 0.9% | Dec 25, 1999 | Paramount Pictures |
| 56 | Ride with the Devil | - | - | - | $118,380 | 60 | $635,096 | 18.6% | Nov 26, 1999 | USA Films |
| 57 | Galapagos | - | - | - | $118,036 | 14 | $18,630,372 | 0.6% | Oct 29, 1999 | IMAX |
| 58 | Everest | - | - | - | $115,774 | 62 | $87,178,599 | 0.1% | Mar 6, 1998 | MacGillivray Freeman Films |
| 59 | Titus | - | - | - | $114,419 | 35 | $2,007,290 | 5.7% | Dec 25, 1999 | Fox Searchlight Pictures |
| 60 | Topsy-Turvy | - | - | - | $106,494 | 224 | $6,208,548 | 1.7% | Dec 15, 1999 | USA Films |
| 61 | Sunshine | - | - | - | $94,370 | 153 | $5,096,267 | 1.9% | Dec 17, 1999 | Paramount Classics |
| 62 | Music of the Heart | - | - | - | $89,198 | 1,353 | $14,859,394 | 0.6% | Oct 29, 1999 | Miramax |
| 63 | 42 Up | - | - | - | $88,983 | 5 | $300,880 | 29.6% | Nov 17, 1999 | First Run |
| 64 | T-Rex: Back to the Cretaceous | - | - | - | $74,405 | 38 | $53,354,743 | 0.1% | Oct 23, 1998 | IMAX |
| 65 | Laura Cadieux... la suite | - | - | - | $47,224 | 59 | $777,477 | 6.1% | Dec 3, 1999 | Alliance Atlantis Vivafilm |
| 66 | Holy Smoke | - | - | - | $47,069 | 93 | $1,765,545 | 2.7% | Dec 3, 1999 | Miramax |
| 67 | Extreme | - | - | - | $36,932 | 21 | $12,475,172 | 0.3% | Apr 2, 1999 | IMAX |
| 68 | My Dog Skip | - | - | - | $23,570 | 2,331 | $34,134,641 | <0.1% | Jan 14, 2000 | Warner Bros. |
| 69 | The Life and Times of Hank Greenberg | - | - | - | $12,485 | 31 | $1,712,385 | 0.7% | Jan 12, 2000 | Cowboy Pictures |
