Winter 1999/2000
| Title | Opening | Closing | Gross | Theaters | 1st Wk % | Per Scrn | Distributor | |||||
| Total | Opening | Opening | Widest | |||||||||
| (Nov 10 - Feb 17) | ||||||||||||
| 1 | Toy Story 2 | 11-19-99 | 07-20-00 | 245,823,397 | 57,388,839 | 1 | 3257 | 23.33 | 75,530 | Buena Vista | ||
| 2 | Stuart Little | 12-17-99 | 04-30-00 | 140,015,224 | 15,018,223 | 2878 | 3151 | 10.73 | 44,435 | Sony | ||
| 3 | Green Mile, The | 12-10-99 | 05-18-00 | 136,801,374 | 18,017,152 | 2875 | 2875 | 13.17 | 47,583 | Warner Bros. | ||
| 4 | World Is Not Enough, The | 11-19-99 | 04-27-00 | 126,930,660 | 35,519,007 | 3163 | 3163 | 27.98 | 40,130 | MGM/UA | ||
| 5 | Sleepy Hollow | 11-19-99 | 05-11-00 | 101,068,340 | 30,060,467 | 3064 | 3069 | 29.74 | 32,932 | Paramount | ||
| 6 | Scream 3 | 02-04-00 | 06-22-00 | 89,138,076 | 34,713,342 | 3467 | 3467 | 39.00 | 25,671 | Miramax | ||
| 7 | Pokémon : The First Movie | 11-10-99 | 02-25-00 | 85,693,123 | 31,036,678 | 3043 | 3043 | 36.22 | 28,161 | Warner Bros. | ||
| 8 | Talented Mr. Ripley, The | 12-25-99 | 04-27-00 | # | 81,292,135 | 12,738,237 | 2307 | 2369 | 15.67 | 34,315 | Paramount | |
| 9 | Any Given Sunday | 12-22-99 | 03-30-00 | 75,530,832 | 13,584,625 | 2505 | 2505 | 17.99 | 30,152 | Warner Bros. | ||
| 10 | Galaxy Quest | 12-25-99 | 03-30-00 | # | 70,302,055 | 7,012,630 | 2412 | 2450 | 9.98 | 28,695 | DreamWorks | |
| 11 | End of Days | 11-24-99 | 03-09-00 | 66,889,403 | 20,523,595 | 2592 | 2652 | 30.68 | 25,222 | Universal | ||
| 12 | Deuce Bigalow : Male Gigolo | 12-10-99 | 04-27-00 | 65,535,067 | 12,224,016 | 2151 | 2162 | 18.65 | 30,312 | Buena Vista | ||
| 13 | Snow Day | 02-11-00 | 07-06-00 | 59,993,940 | 14,331,819 | 2664 | 2717 | 23.89 | 22,081 | Paramount | ||
| 14 | Bicentennial Man | 12-17-99 | 06-01-00 | 58,220,775 | 8,234,926 | 2518 | 2767 | 14.14 | 21,041 | Buena Vista | ||
| 15 | Cider House Rules, The | 12-10-99 | 06-29-00 | 57,547,209 | 3,077,420 | 8 | 1734 | 5.35 | 33,188 | Miramax | ||
| 16 | Next Friday | 01-12-00 | 05-18-00 | 57,198,674 | 14,465,156 | 1103 | 1420 | 25.29 | 40,281 | New Line | ||
| 17 | Hurricane, The | 12-29-99 | 04-20-00 | 50,668,906 | 9,014,805 | 11 | 2148 | 17.79 | 23,589 | Universal | ||
| 18 | Fantasia 2000 | 01-01-00 | 04-30-00 | 49,550,091 | 2,290,525 | 54 | 54 | 4.62 | 917,594 | Buena Vista | ||
| 19 | Tigger Movie, The | 02-11-00 | 07-20-00 | 45,542,421 | 9,427,532 | 2723 | 2818 | 20.70 | 16,161 | Buena Vista | ||
| 20 | Beach, The | 02-11-00 | 05-11-00 | 39,778,599 | 15,277,921 | 2547 | 2587 | 38.41 | 15,376 | Fox | ||
| 21 | Anna and the King | 12-17-99 | 04-13-00 | 39,251,128 | 5,223,416 | 2132 | 2132 | 13.31 | 18,410 | Fox | ||
| 22 | Man on the Moon | 12-22-99 | 02-24-00 | 34,607,430 | 7,515,585 | 2079 | 2079 | 21.72 | 16,646 | Universal | ||
| 23 | My Dog Skip | 01-12-00 | 07-06-00 | 34,134,641 | 5,863,545 | 9 | 2331 | 17.18 | 14,644 | Warner Bros. | ||
| 24 | Dogma | 11-12-99 | 03-30-00 | 30,651,422 | 8,669,945 | 1269 | 1292 | 28.29 | 23,724 | Lions Gate | ||
| 25 | Girl, Interrupted | 12-21-99 | 03-09-00 | 28,502,283 | 8,123,767 | 9 | 1935 | 28.50 | 14,730 | Sony | ||
| 26 | Magnolia | 12-17-99 | 05-18-00 | 22,450,975 | 5,694,588 | 7 | 1086 | 25.36 | 20,673 | New Line | ||
| 27 | Down To You | 01-21-00 | 03-30-00 | 19,624,554 | 7,602,507 | 1971 | 2003 | 38.74 | 9,798 | Miramax | ||
| 28 | Anywhere But Here | 11-12-99 | 02-25-00 | 18,653,615 | 5,607,137 | 1672 | 1686 | 30.06 | 11,064 | Fox | ||
| 29 | Eye of the Beholder | 01-28-00 | 03-30-00 | 16,489,515 | 5,959,447 | 1751 | 1751 | 36.14 | 9,417 | Destination | ||
| 30 | Snow Falling on Cedars | 12-22-99 | 03-16-00 | 14,417,593 | 3,910,055 | 3 | 1155 | 27.12 | 12,483 | Universal | ||