1999 Top-Grossing Movies (Inflation-Adjusted Dollars)
Note: This chart ranks movies by the amount they earned during 1999. It includes movies released in previous years that earned money during 1999. For example, a movie released over Thanksgiving in 1998 will most likely earn money in 1998 and 1999. Click on the individual movie to see its total gross over all the years in which it played.
Inflation-adjusted figures are based on ticket sale estimates.
| Rank | Movie | Release Date | Distributor | Genre | 1999 Gross Infl. adj. |
Tickets Sold |
|---|---|---|---|---|---|---|
| 1 | Star Wars Ep. I: The Phantom … | May 19, 1999 | 20th Century Fox | Adventure | $1,013,405,997 | 84,732,942 |
| 2 | The Sixth Sense | Aug 6, 1999 | Walt Disney | Thriller/Suspense | $650,705,213 | 54,406,790 |
| 3 | Austin Powers: The Spy Who Sh… | Jun 10, 1999 | New Line | Comedy | $484,892,759 | 40,542,873 |
| 4 | Toy Story 2 | Nov 19, 1999 | Walt Disney | Adventure | $470,574,205 | 39,345,669 |
| 5 | The Matrix | Mar 31, 1999 | Warner Bros. | Action | $403,492,855 | 33,736,861 |
| 6 | Tarzan | Jun 16, 1999 | Walt Disney | Adventure | $402,366,475 | 33,642,681 |
| 7 | Big Daddy | Jun 25, 1999 | Sony Pictures | Comedy | $384,885,502 | 32,181,062 |
| 8 | The Mummy | May 7, 1999 | Universal | Adventure | $365,504,722 | 30,560,595 |
| 9 | Runaway Bride | Jul 30, 1999 | Paramount Pictures | Romantic Comedy | $358,240,486 | 29,953,217 |
| 10 | The Blair Witch Project | Jul 14, 1999 | Artisan | Horror | $330,875,517 | 27,665,177 |
| 11 | Notting Hill | May 28, 1999 | Universal | Romantic Comedy | $273,313,494 | 22,852,299 |
| 12 | The World is Not Enough | Nov 19, 1999 | MGM | Action | $272,873,992 | 22,815,551 |
| 13 | Double Jeopardy | Sep 24, 1999 | Paramount Pictures | Action | $268,469,315 | 22,447,267 |
| 14 | Wild Wild West | Jun 30, 1999 | Warner Bros. | Western | $267,936,210 | 22,402,693 |
| 15 | Analyze This | Mar 5, 1999 | Warner Bros. | Comedy | $251,497,547 | 21,028,223 |
| 16 | The General’s Daughter | Jun 18, 1999 | Paramount Pictures | Drama | $241,803,541 | 20,217,687 |
| 17 | American Pie | Jul 9, 1999 | Universal | Comedy | $239,673,098 | 20,039,557 |
| 18 | Inspector Gadget | Jul 23, 1999 | Walt Disney | Adventure | $229,283,477 | 19,170,859 |
| 19 | Shakespeare in Love | Dec 11, 1998 | Miramax | Romantic Comedy | $221,311,214 | 18,504,282 |
| 20 | Sleepy Hollow | Nov 19, 1999 | Paramount Pictures | Horror | $218,575,408 | 18,275,535 |
| 21 | The Haunting | Jul 23, 1999 | Dreamworks SKG | Horror | $214,688,839 | 17,950,572 |
| 22 | Patch Adams | Dec 25, 1998 | Universal | Comedy | $209,048,011 | 17,478,931 |
| 23 | Entrapment | Apr 30, 1999 | 20th Century Fox | Thriller/Suspense | $206,492,216 | 17,265,235 |
| 24 | Pokemon: The First Movie | Nov 10, 1999 | Warner Bros. | Adventure | $197,978,257 | 16,553,365 |
| 25 | Payback | Feb 5, 1999 | Paramount Pictures | Action | $191,939,450 | 16,048,449 |
| 26 | Deep Blue Sea | Jul 28, 1999 | Warner Bros. | Horror | $173,392,285 | 14,497,683 |
| 27 | American Beauty | Sep 15, 1999 | Dreamworks SKG | Drama | $167,199,423 | 13,979,884 |
| 28 | The Thomas Crown Affair | Aug 6, 1999 | MGM | Thriller/Suspense | $163,113,609 | 13,638,261 |
| 29 | Stuart Little | Dec 17, 1999 | Sony Pictures | Adventure | $162,152,173 | 13,557,874 |
| 30 | Blue Streak | Sep 17, 1999 | Sony Pictures | Action | $159,531,193 | 13,338,728 |
| 31 | The Green Mile | Dec 10, 1999 | Warner Bros. | Drama | $158,903,197 | 13,286,220 |
| 32 | Bowfinger | Aug 13, 1999 | Universal | Comedy | $156,245,840 | 13,064,033 |
| 33 | Life | Apr 16, 1999 | Universal | Comedy | $150,715,466 | 12,601,628 |
| 34 | The Bone Collector | Nov 5, 1999 | Universal | Thriller/Suspense | $150,178,683 | 12,556,746 |
| 35 | She’s All That | Jan 29, 1999 | Miramax | Romantic Comedy | $149,075,064 | 12,464,470 |
| 36 | End of Days | Nov 24, 1999 | Universal | Action | $148,758,386 | 12,437,992 |
| 37 | Three Kings | Oct 1, 1999 | Warner Bros. | Black Comedy | $139,430,772 | 11,658,091 |
| 38 | A Civil Action | Dec 25, 1998 | Walt Disney | Drama | $133,131,057 | 11,131,359 |
| 39 | Stepmom | Dec 25, 1998 | Sony/TriStar | Drama | $131,279,427 | 10,976,541 |
| 40 | Eyes Wide Shut | Jul 16, 1999 | Warner Bros. | Drama | $130,989,499 | 10,952,299 |
| 41 | Never Been Kissed | Apr 9, 1999 | 20th Century Fox | Romantic Comedy | $130,605,924 | 10,920,228 |
| 42 | Forces of Nature | Mar 19, 1999 | Dreamworks SKG | Romantic Comedy | $124,545,695 | 10,413,520 |
| 43 | Varsity Blues | Jan 15, 1999 | Paramount Pictures | Drama | $124,530,366 | 10,412,238 |
| 44 | Message in a Bottle | Feb 12, 1999 | Warner Bros. | Drama | $124,306,317 | 10,393,505 |
| 45 | South Park: Bigger, Longer & … | Jun 30, 1999 | Paramount Pictures | Musical | $122,513,727 | 10,243,623 |
| 46 | You’ve Got Mail | Dec 18, 1998 | Warner Bros. | Romantic Comedy | $122,271,087 | 10,223,335 |
| 47 | Stigmata | Sep 10, 1999 | MGM | Horror | $117,751,533 | 9,845,445 |
| 48 | La vita è bella | Oct 23, 1998 | Miramax | Drama | $111,269,959 | 9,303,508 |
| 49 | Deuce Bigalow: Male Gigolo | Dec 10, 1999 | Walt Disney | Comedy | $109,131,610 | 9,124,716 |
| 50 | The Prince of Egypt | Dec 18, 1998 | Dreamworks SKG | Adventure | $108,557,954 | 9,076,752 |
| 51 | House on Haunted Hill | Oct 29, 1999 | Warner Bros. | Horror | $95,326,436 | 7,970,437 |
| 52 | Cruel Intentions | Mar 5, 1999 | Sony Pictures | Drama | $89,939,895 | 7,520,058 |
| 53 | 10 Things I Hate About You | Mar 31, 1999 | Walt Disney | Romantic Comedy | $89,883,558 | 7,515,348 |
| 54 | My Favorite Martian | Feb 12, 1999 | Walt Disney | Comedy | $86,757,324 | 7,253,957 |
| 55 | Fight Club | Oct 15, 1999 | 20th Century Fox | Drama | $85,968,617 | 7,188,011 |
| 56 | Any Given Sunday | Dec 22, 1999 | Warner Bros. | Drama | $85,464,559 | 7,145,866 |
| 57 | 8MM | Feb 26, 1999 | Sony Pictures | Thriller/Suspense | $85,423,361 | 7,142,421 |
| 58 | The Thin Red Line | Dec 23, 1998 | 20th Century Fox | Drama | $84,146,042 | 7,035,622 |
| 59 | For Love of the Game | Sep 17, 1999 | Universal | Drama | $82,845,696 | 6,926,898 |
| 60 | A Bug’s Life | Nov 20, 1998 | Walt Disney | Adventure | $82,662,145 | 6,911,551 |
| 61 | Instinct | Jun 4, 1999 | Walt Disney | Thriller/Suspense | $80,294,936 | 6,713,623 |
| 62 | Mickey Blue Eyes | Aug 20, 1999 | Warner Bros. | Romantic Comedy | $79,727,860 | 6,666,209 |
| 63 | Bicentennial Man | Dec 17, 1999 | Walt Disney | Drama | $78,582,850 | 6,570,472 |
| 64 | The Best Man | Oct 22, 1999 | Universal | Romantic Comedy | $78,383,957 | 6,553,842 |
| 65 | The 13th Warrior | Aug 27, 1999 | Walt Disney | Action | $76,974,343 | 6,435,982 |
| 66 | October Sky | Feb 19, 1999 | Universal | Drama | $76,682,164 | 6,411,552 |
| 67 | Lake Placid | Jul 16, 1999 | 20th Century Fox | Horror | $74,798,059 | 6,254,018 |
| 68 | Random Hearts | Oct 8, 1999 | Sony Pictures | Drama | $73,113,561 | 6,113,174 |
| 69 | Mighty Joe Young | Dec 25, 1998 | Walt Disney | Adventure | $71,833,005 | 6,006,104 |
| 70 | Superstar | Jan 1, 1999 | Paramount Pictures | Comedy | $70,984,987 | 5,935,199 |
| 71 | Mystery Men | Aug 6, 1999 | Universal | Comedy | $70,069,616 | 5,858,664 |
| 72 | The Talented Mr. Ripley | Dec 24, 1999 | Paramount Pictures | Thriller/Suspense | $69,365,646 | 5,799,803 |
| 73 | Dogma | Nov 12, 1999 | Lionsgate | Comedy | $68,236,179 | 5,705,366 |
| 74 | The Out-of-Towners | Apr 2, 1999 | Paramount Pictures | Comedy | $67,202,298 | 5,618,921 |
| 75 | The Other Sister | Feb 26, 1999 | Walt Disney | Romantic Comedy | $65,468,350 | 5,473,942 |
| 76 | Baby Geniuses | Mar 12, 1999 | Sony Pictures | Adventure | $63,923,587 | 5,344,781 |
| 77 | The Story of Us | Oct 15, 1999 | Universal | Comedy | $63,802,433 | 5,334,652 |
| 78 | Mysteries of Egypt | Jul 16, 1998 | Sony Pictures | Documentary | $63,666,673 | 5,323,300 |
| 79 | Blast from the Past | Feb 12, 1999 | New Line | Romantic Comedy | $62,377,076 | 5,215,475 |
| 80 | The Insider | Nov 5, 1999 | Walt Disney | Drama | $61,483,087 | 5,140,726 |
| 81 | Saving Private Ryan | Jul 24, 1998 | Dreamworks SKG | Drama | $60,615,321 | 5,068,171 |
| 82 | The Wood | Jul 16, 1999 | Paramount Pictures | Comedy | $58,998,680 | 4,933,000 |
| 83 | Arlington Road | Jul 9, 1999 | Sony Pictures | Thriller/Suspense | $57,357,384 | 4,795,768 |
| 84 | T-Rex: Back to the Cretaceous | Oct 23, 1998 | IMAX Films | Adventure | $57,311,616 | 4,791,941 |
| 85 | The Iron Giant | Aug 4, 1999 | Warner Bros. | Adventure | $54,524,663 | 4,558,918 |
| 86 | EDtv | Mar 26, 1999 | Universal | Comedy | $52,786,654 | 4,413,600 |
| 87 | At First Sight | Jan 15, 1999 | MGM | Drama | $52,563,369 | 4,394,931 |
| 88 | The Faculty | Dec 25, 1998 | Miramax | Horror | $51,187,752 | 4,279,912 |
| 89 | The Bachelor | Nov 5, 1999 | New Line | Romantic Comedy | $50,068,270 | 4,186,310 |
| 90 | Stir of Echoes | Sep 10, 1999 | Artisan | Horror | $49,754,276 | 4,160,056 |
| 91 | Anna and the King | Dec 17, 1999 | 20th Century Fox | Drama | $48,294,386 | 4,037,992 |
| 92 | Man on the Moon | Dec 22, 1999 | Universal | Drama | $47,008,921 | 3,930,512 |
| 93 | Galaxy Quest | Dec 24, 1999 | Dreamworks SKG | Comedy | $46,877,079 | 3,919,488 |
| 94 | Enemy of the State | Nov 20, 1998 | Walt Disney | Action | $45,967,000 | 3,843,395 |
| 95 | Waking Ned Devine | Nov 20, 1998 | 20th Century Fox | Comedy | $45,799,612 | 3,829,399 |
| 96 | Doug's 1st Movie | Mar 26, 1999 | Walt Disney | Adventure | $45,724,095 | 3,823,085 |
| 97 | Summer of Sam | Jul 2, 1999 | Walt Disney | Thriller/Suspense | $45,410,637 | 3,796,876 |
| 98 | An Ideal Husband | Jun 18, 1999 | Miramax | Romantic Comedy | $43,656,293 | 3,650,192 |
| 99 | Being John Malkovich | Oct 29, 1999 | USA Films | Black Comedy | $42,952,336 | 3,591,332 |
| 100 | Anywhere But Here | Nov 12, 1999 | 20th Century Fox | Drama | $42,884,802 | 3,585,685 |
| 101 | Everest | Mar 6, 1998 | Documentary | $42,529,689 | 3,555,994 | |
| 102 | Drive Me Crazy | Oct 1, 1999 | 20th Century Fox | Romantic Comedy | $41,938,832 | 3,506,591 |
| 103 | The Rage: Carrie 2 | Mar 12, 1999 | MGM | Horror | $41,806,055 | 3,495,490 |
| 104 | Rushmore | Dec 11, 1998 | Walt Disney | Black Comedy | $40,146,958 | 3,356,769 |
| 105 | Go! | Apr 9, 1999 | Sony Pictures | Black Comedy | $39,652,351 | 3,315,414 |
| 106 | True Crime | Mar 19, 1999 | Warner Bros. | Drama | $39,165,089 | 3,274,673 |
| 107 | Bringing Out The Dead | Oct 22, 1999 | Paramount Pictures | Black Comedy | $38,802,796 | 3,244,381 |
| 108 | Muppets From Space | Jul 14, 1999 | Sony Pictures | Adventure | $38,386,858 | 3,209,604 |
| 109 | Star Trek: Insurrection | Dec 11, 1998 | Paramount Pictures | Adventure | $38,141,502 | 3,189,089 |
| 110 | A Midsummer Night's Dream | May 14, 1999 | Fox Searchlight | Romantic Comedy | $37,838,780 | 3,163,778 |
| 111 | The Corruptor | Mar 12, 1999 | New Line | Action | $35,702,229 | 2,985,136 |
| 112 | The Rugrats Movie | Nov 20, 1998 | Paramount Pictures | Adventure | $35,344,821 | 2,955,253 |
| 113 | Election | Apr 23, 1999 | Paramount Pictures | Black Comedy | $35,031,396 | 2,929,046 |
| 114 | Music of the Heart | Oct 29, 1999 | Miramax | Drama | $34,738,284 | 2,904,538 |
| 115 | Elizabeth | Nov 6, 1998 | Gramercy | Drama | $34,232,037 | 2,862,210 |
| 116 | Tea with Mussolini | May 14, 1999 | MGM | Drama | $33,892,648 | 2,833,833 |
| 117 | A Simple Plan | Dec 11, 1998 | Paramount Pictures | Thriller/Suspense | $33,685,394 | 2,816,505 |
| 118 | The Messenger: The Story of J… | Nov 12, 1999 | Sony Pictures | Drama | $33,313,476 | 2,785,408 |
| 119 | Virus | Jan 15, 1999 | Universal | Action | $32,985,798 | 2,758,010 |
| 120 | In Too Deep | Aug 25, 1999 | Gramercy | Thriller/Suspense | $32,968,025 | 2,756,524 |
| 121 | The Waterboy | Nov 6, 1998 | Walt Disney | Comedy | $31,999,642 | 2,675,555 |
| 122 | The Deep End of the Ocean | Mar 12, 1999 | Sony Pictures | Drama | $31,625,682 | 2,644,288 |
| 123 | The Mod Squad | Mar 26, 1999 | MGM | Action | $31,218,543 | 2,610,246 |
| 124 | The Omega Code | Oct 15, 1999 | Providence Entert… | Action | $28,902,235 | 2,416,574 |
| 125 | The King and I | Mar 19, 1999 | Warner Bros. | Musical | $28,403,682 | 2,374,890 |
| 126 | In Dreams | Jan 15, 1999 | Dreamworks SKG | Horror | $28,081,708 | 2,347,969 |
| 127 | The Thirteenth Floor | May 28, 1999 | Sony Pictures | Thriller/Suspense | $27,806,656 | 2,324,971 |
| 128 | The Adventures of Elmo in Gro… | Oct 1, 1999 | Sony Pictures | Adventure | $27,391,362 | 2,290,248 |
| 129 | The Muse | Aug 27, 1999 | October Films | Comedy | $27,345,443 | 2,286,408 |
| 130 | Wing Commander | Mar 12, 1999 | 20th Century Fox | Action | $27,258,493 | 2,279,138 |
| 131 | Chill Factor | Sep 1, 1999 | Warner Bros. | Action | $26,519,101 | 2,217,316 |
| 132 | Cookie's Fortune | Apr 2, 1999 | October Films | Black Comedy | $25,707,354 | 2,149,444 |
| 133 | Office Space | Feb 19, 1999 | Miramax | Black Comedy | $25,485,444 | 2,130,890 |
| 134 | The Astronaut's Wife | Aug 27, 1999 | New Line | Thriller/Suspense | $25,126,750 | 2,100,899 |
| 135 | Drop Dead Gorgeous | Jul 23, 1999 | New Line | Black Comedy | $24,888,590 | 2,080,986 |
| 136 | Three to Tango | Oct 22, 1999 | Warner Bros. | Romantic Comedy | $24,886,158 | 2,080,782 |
| 137 | Universal Soldier II: The Ret… | Aug 20, 1999 | Sony Pictures | Action | $24,596,684 | 2,056,579 |
| 138 | Hak Hap | May 14, 1999 | Artisan | Action | $24,040,725 | 2,010,094 |
| 139 | Bats | Oct 22, 1999 | Sony Pictures | Horror | $23,909,855 | 1,999,152 |
| 140 | Brokedown Palace | Aug 13, 1999 | 20th Century Fox | Drama | $23,814,088 | 1,991,144 |
| 141 | Le Violon rouge | Jun 11, 1999 | Lionsgate | Drama | $23,588,296 | 1,972,266 |
| 142 | Dudley Do-Right | Aug 27, 1999 | Universal | Comedy | $23,116,684 | 1,932,833 |
| 143 | Trippin’ | May 12, 1999 | October Films | Comedy | $21,229,165 | 1,775,014 |
| 144 | Teaching Mrs. Tingle | Aug 20, 1999 | Miramax | Black Comedy | $20,977,974 | 1,754,011 |
| 145 | Mystery, Alaska | Oct 1, 1999 | Walt Disney | Comedy | $20,933,821 | 1,750,319 |
| 146 | Pushing Tin | Apr 23, 1999 | 20th Century Fox | Comedy | $19,797,178 | 1,655,282 |
| 147 | Twin Dragons | Apr 9, 1999 | Miramax | Action | $19,617,298 | 1,640,242 |
| 148 | The Love Letter | May 21, 1999 | Dreamworks SKG | Romantic Comedy | $19,484,978 | 1,629,179 |
| 149 | Outside Providence | Sep 1, 1999 | Miramax | Comedy | $17,209,282 | 1,438,903 |
| 150 | Lola rennt | Jun 18, 1999 | Sony Pictures Cla… | Thriller/Suspense | $16,969,229 | 1,418,831 |
| 151 | Africa's Elephant Kingdom | May 8, 1998 | Discovery/IMAX | Documentary | $16,596,174 | 1,387,639 |
| 152 | Buena Vista Social Club | Jun 4, 1999 | Artisan | Documentary | $16,288,423 | 1,361,908 |
| 153 | Extreme | Mar 23, 1999 | IMAX Films | Documentary | $16,227,166 | 1,356,786 |
| 154 | 200 Cigarettes | Feb 26, 1999 | Paramount Pictures | Romantic Comedy | $16,131,017 | 1,348,747 |
| 155 | Jack Frost | Dec 11, 1998 | Warner Bros. | Comedy | $15,468,023 | 1,293,313 |
| 156 | Lost and Found | Apr 23, 1999 | Warner Bros. | Romantic Comedy | $15,426,175 | 1,289,814 |
| 157 | Dick | Aug 4, 1999 | Sony Pictures | Comedy | $14,695,019 | 1,228,681 |
| 158 | Affliction | Dec 30, 1998 | Lionsgate | Drama | $14,621,041 | 1,222,495 |
| 159 | Foolish | Apr 9, 1999 | Artisan | Comedy | $14,189,335 | 1,186,399 |
| 160 | Les Boys II | Oct 23, 1998 | Lionsgate | Comedy | $14,066,495 | 1,176,128 |
| 161 | Light It Up | Nov 10, 1999 | 20th Century Fox | Drama | $13,705,840 | 1,145,973 |
| 162 | Central do Brasil | Nov 20, 1998 | Sony Pictures Cla… | Drama | $12,747,957 | 1,065,883 |
| 163 | Island of the Sharks | Apr 30, 1999 | IMAX Films | Documentary | $12,258,826 | 1,024,985 |
| 164 | Rush Hour | Sep 18, 1998 | New Line | Action | $11,979,661 | 1,001,644 |
| 165 | Jakob the Liar | Sep 24, 1999 | Sony Pictures | Drama | $11,669,007 | 975,669 |
| 166 | A Walk on the Moon | Mar 26, 1999 | Miramax | Drama | $11,164,206 | 933,462 |
| 167 | Hilary and Jackie | Dec 30, 1998 | October Films | Drama | $11,159,313 | 933,053 |
| 168 | Gods and Monsters | Nov 6, 1998 | Lionsgate | Drama | $11,118,605 | 929,649 |
| 169 | Mumford | Sep 24, 1999 | Walt Disney | Comedy | $10,734,733 | 897,553 |
| 170 | Simply Irresistible | Feb 5, 1999 | 20th Century Fox | Romantic Comedy | $10,356,675 | 865,943 |
| 171 | Flawless | Nov 24, 1999 | MGM | Drama | $10,346,620 | 865,101 |
| 172 | The Straight Story | Oct 15, 1999 | Walt Disney | Drama | $10,302,419 | 861,406 |
| 173 | Encounter in the Third Dimens… | Feb 26, 1999 | nWave Pictures | Documentary | $10,051,928 | 840,462 |
| 174 | Detroit Rock City | Aug 13, 1999 | New Line | Comedy | $9,928,483 | 830,141 |
| 175 | The Cider House Rules | Dec 10, 1999 | Miramax | Drama | $9,891,758 | 827,070 |
| 176 | Gloria | Jan 22, 1999 | Sony Pictures | Drama | $9,811,657 | 820,373 |
| 177 | Le Diner de Cons | Jul 9, 1999 | Lionsgate | Comedy | $9,570,627 | 800,220 |
| 178 | The Winslow Boy | Apr 30, 1999 | Sony Pictures Cla… | Drama | $9,554,698 | 798,888 |
| 179 | Idle Hands | Apr 30, 1999 | Sony Pictures | Horror | $9,473,217 | 792,075 |
| 180 | Little Voice | Dec 4, 1998 | Miramax | Musical | $9,232,428 | 771,942 |
| 181 | Playing by Heart | Dec 30, 1998 | Miramax | Drama | $9,227,277 | 771,511 |
| 182 | Lock, Stock and Two Smoking B… | Mar 5, 1999 | Gramercy | Black Comedy | $8,744,142 | 731,116 |
| 183 | Thrill Ride: The Science of F… | Jul 11, 1997 | Sony Pictures Cla… | Documentary | $8,103,397 | 677,541 |
| 184 | The School of Flesh | Feb 26, 1999 | Stratosphere Ente… | Drama | $7,908,270 | 661,227 |
| 185 | Fifty | Oct 29, 1999 | Warren Miller Ent… | Documentary | $7,835,778 | 655,165 |
| 186 | Elvis Gratton 2 | Jul 2, 1999 | Lionsgate | Comedy | $7,807,601 | 652,809 |
| 187 | Down in the Delta | Dec 25, 1998 | Miramax | Drama | $7,452,464 | 623,116 |
| 188 | Jawbreaker | Feb 19, 1999 | Sony Pictures | Black Comedy | $7,243,852 | 605,673 |
| 189 | The Limey | Oct 8, 1999 | Artisan | Drama | $7,112,030 | 594,651 |
| 190 | Wolves | Feb 26, 1999 | Primesco | Documentary | $6,715,053 | 561,459 |
| 191 | eXistenZ | Apr 23, 1999 | Miramax | Thriller/Suspense | $6,687,281 | 559,137 |
| 192 | Love Stinks | Sep 10, 1999 | Independent Artis… | Black Comedy | $6,577,473 | 549,956 |
| 193 | Boys Don't Cry | Oct 8, 1999 | Fox Searchlight | Drama | $6,349,790 | 530,918 |
| 194 | Marius et Jeannette | Dec 5, 1997 | New Yorker | Romantic Comedy | $6,010,060 | 502,513 |
| 195 | Babe: Pig in the City | Nov 25, 1998 | Universal | Adventure | $6,003,120 | 501,933 |
| 196 | Mansfield Park | Nov 18, 1999 | Miramax | Drama | $5,820,494 | 486,663 |
| 197 | Princess Mononoke (もののけ姫) | Oct 29, 1999 | Miramax | Action | $5,650,394 | 472,441 |
| 198 | Windhorse | Feb 12, 1999 | Shadow | Drama | $5,407,938 | 452,169 |
| 199 | Fantasia 2000 | Dec 31, 1999 | Walt Disney | Musical | $5,392,653 | 450,890 |
| 200 | Liberty Heights | Nov 17, 1999 | Warner Bros. | Drama | $5,383,540 | 450,128 |
| 201 | A Dog of Flanders | Aug 27, 1999 | Warner Bros. | Drama | $5,098,626 | 426,306 |
| 202 | Siegfried & Roy: Masters of t… | Oct 1, 1999 | IMAX Films | Documentary | $5,090,456 | 425,623 |
| 203 | Todo sobre mi madre | Nov 5, 1999 | Sony Pictures Cla… | Drama | $5,022,755 | 419,962 |
| 204 | Conte d'automne | Jul 9, 1999 | October Films | Drama | $4,901,860 | 409,855 |
| 205 | Ravenous | Mar 19, 1999 | 20th Century Fox | Horror | $4,855,586 | 405,985 |
| 206 | There’s Something About Mary | Jul 15, 1998 | 20th Century Fox | Romantic Comedy | $4,852,424 | 405,721 |
| 207 | Trick | Jul 23, 1999 | Fine Line | Comedy | $4,825,424 | 403,464 |
| 208 | Besieged | May 21, 1999 | Fine Line | Drama | $4,785,462 | 400,122 |
| 209 | Three Seasons | Apr 30, 1999 | October Films | Drama | $4,753,952 | 397,488 |
| 210 | Better Than Chocolate | Aug 13, 1999 | Trimark | Romantic Comedy | $4,735,157 | 395,916 |
| 211 | Hum Saath-Saath Hain | Sep 10, 1999 | Eros Entertainment | Musical | $4,720,654 | 394,704 |
| 212 | Limbo | Jun 4, 1999 | Sony Pictures | Drama | $4,703,498 | 393,269 |
| 213 | Taal | Aug 13, 1999 | Eros Entertainment | Musical | $4,662,512 | 389,842 |
| 214 | Antz | Oct 2, 1998 | Dreamworks SKG | Adventure | $4,657,349 | 389,410 |
| 215 | Crazy in Alabama | Oct 22, 1999 | Sony Pictures | Drama | $4,600,838 | 384,685 |
| 216 | Happy, Texas | Oct 1, 1999 | Miramax | Comedy | $4,575,993 | 382,608 |
| 217 | Goodbye, Lover | Apr 16, 1999 | Warner Bros. | Comedy | $4,568,106 | 381,949 |
| 218 | Wildfire: Feel The Heat | Mar 12, 1999 | Primesco | Documentary | $4,357,120 | 364,307 |
| 219 | Pleasantville | Oct 23, 1998 | New Line | Comedy | $4,252,715 | 355,578 |
| 220 | The Dreamlife of Angels | Apr 2, 1999 | Sony Pictures Cla… | Drama | $4,084,366 | 341,502 |
| 221 | Tango | Feb 12, 1999 | Sony Pictures Cla… | Drama | $3,972,488 | 332,148 |
| 222 | Astérix et Obélix contre César | Jun 4, 1999 | Distributor Unkno… | Adventure | $3,770,416 | 315,252 |
| 223 | Romance | Sep 17, 1999 | Trimark | Drama | $3,733,126 | 312,134 |
| 224 | The End of the Affair | Dec 3, 1999 | Sony Pictures | Drama | $3,661,759 | 306,167 |
| 225 | Hurlyburly | Dec 25, 1998 | Fine Line | Comedy | $3,541,695 | 296,128 |
| 226 | Dancing at Lughnasa | Nov 13, 1998 | Sony Pictures Cla… | Drama | $3,367,230 | 281,541 |
| 227 | Meet Joe Black | Nov 13, 1998 | Universal | Drama | $3,215,145 | 268,825 |
| 228 | Hideous Kinky | Apr 16, 1999 | Stratosphere Ente… | Drama | $2,973,016 | 248,580 |
| 229 | Get Real | Apr 30, 1999 | Paramount Pictures | Comedy | $2,713,157 | 226,853 |
| 230 | Tumbleweeds | Nov 24, 1999 | Fine Line | Drama | $2,591,584 | 216,687 |
| 231 | I Still Know What You Did Las… | Nov 13, 1998 | Sony Pictures | Horror | $2,587,890 | 216,379 |
| 232 | This is My Father | May 7, 1999 | Sony Pictures Cla… | Drama | $2,550,371 | 213,242 |
| 233 | The General | Dec 18, 1998 | Sony Pictures Cla… | Drama | $2,535,727 | 212,017 |
| 234 | The Siege | Nov 6, 1998 | 20th Century Fox | Action | $2,410,514 | 201,548 |
| 235 | Psycho | Dec 4, 1998 | Universal | Horror | $2,393,813 | 200,152 |
| 236 | The King of Masks | Apr 30, 1999 | Goldwyn Entertain… | Drama | $2,389,398 | 199,782 |
| 237 | Straight From The Heart | Jun 18, 1999 | Video Sound | Musical | $2,371,861 | 198,316 |
| 238 | Xiu Xiu: The Sent Down Girl | May 7, 1999 | Stratosphere Ente… | Drama | $2,369,676 | 198,133 |
| 239 | Another Day in Paradise | Dec 30, 1998 | Trimark | Drama | $2,339,972 | 195,650 |
| 240 | Twin Falls Idaho | Jul 30, 1999 | Sony Pictures Cla… | Drama | $2,319,819 | 193,965 |
| 241 | Bacheha-Ye aseman | Jan 22, 1999 | Miramax | Adventure | $2,198,787 | 183,845 |
| 242 | The Castle | May 7, 1999 | Miramax | Comedy | $2,130,698 | 178,152 |
| 243 | Edge of Seventeen | Apr 30, 1999 | Strand Releasing | Comedy | $2,044,378 | 170,934 |
| 244 | Sweet and Lowdown | Dec 3, 1999 | Sony Pictures Cla… | Romantic Comedy | $2,042,436 | 170,772 |
| 245 | Illuminata | Aug 6, 1999 | Artisan | Drama | $1,969,730 | 164,693 |
| 246 | Galapagos | Oct 29, 1999 | IMAX Films | Documentary | $1,898,167 | 158,709 |
| 247 | Wandafuru raifu | May 12, 1999 | Artistic License | Drama | $1,843,681 | 154,153 |
| 248 | Cradle Will Rock | Dec 8, 1999 | Walt Disney | Drama | $1,815,311 | 151,781 |
| 249 | Magnolia | Dec 17, 1999 | New Line | Drama | $1,800,934 | 150,579 |
| 250 | Felicia's Journey | Nov 12, 1999 | Artisan | Drama | $1,793,833 | 149,986 |
| 251 | Wings of Courage | Apr 21, 1995 | Sony Pictures Cla… | Drama | $1,772,658 | 148,215 |
| 252 | Body Shots | Oct 22, 1999 | New Line | Drama | $1,647,947 | 137,788 |
| 253 | Mark Twain's America 3D | Jul 3, 1998 | Sony Pictures Cla… | Documentary | $1,581,209 | 132,208 |
| 254 | American History X | Oct 30, 1998 | New Line | Drama | $1,570,492 | 131,312 |
| 255 | Laura Cadieux .. La Suite | Dec 3, 1999 | Alliance Atlantis | Comedy | $1,510,595 | 126,303 |
| 256 | My Life So Far | Jul 23, 1999 | Miramax | Drama | $1,496,460 | 125,122 |
| 257 | Trekkies | May 21, 1999 | Paramount Pictures | Documentary | $1,453,027 | 121,491 |
| 258 | Guinevere | Sep 24, 1999 | Miramax | Drama | $1,446,035 | 120,906 |
| 259 | The Third Man | Feb 2, 1950 | Rialto Pictures | Thriller/Suspense | $1,404,003 | 117,392 |
| 260 | Jerry Springer: Ringmaster | Nov 25, 1998 | Artisan | Black Comedy | $1,300,956 | 108,776 |
| 261 | Urban Legend | Sep 25, 1998 | Sony Pictures | Horror | $1,276,457 | 106,727 |
| 262 | The Hurricane | Dec 29, 1999 | Universal | Drama | $1,274,223 | 106,540 |
| 263 | 20 Dates | Feb 26, 1999 | Fox Searchlight | Comedy | $1,263,727 | 105,663 |
| 264 | Baadshah | Aug 27, 1999 | Eros Entertainment | Action | $1,259,616 | 105,319 |
| 265 | Across The Sea of Time | Oct 20, 1995 | Sony Pictures Cla… | Adventure | $1,188,949 | 99,410 |
| 266 | Lovers of the Arctic Circle | Apr 9, 1999 | Fine Line | Drama | $1,187,108 | 99,256 |
| 267 | Ride With the Devil | Nov 24, 1999 | USA Films | Western | $1,156,139 | 96,667 |
| 268 | The Harmonists | Mar 12, 1999 | Miramax | $1,129,674 | 94,454 | |
| 269 | Still Crazy | Jan 22, 1999 | Sony Pictures | Comedy | $1,125,142 | 94,075 |
| 270 | Plunkett & Macleane | Oct 1, 1999 | Gramercy | $1,121,678 | 93,786 | |
| 271 | Earth | Sep 10, 1999 | Zeitgeist | Drama | $1,119,748 | 93,624 |
| 272 | Dillagi | Nov 19, 1999 | $1,090,429 | 91,173 | ||
| 273 | American Movie: The Making of… | Nov 5, 1999 | Sony Pictures Cla… | Documentary | $1,081,902 | 90,460 |
| 274 | Lucie Aubrac | Sep 17, 1999 | USA Films | $1,079,595 | 90,267 | |
| 275 | Relax… It's Just Sex | Apr 30, 1999 | $1,065,697 | 89,105 | ||
| 276 | Festen | Oct 9, 1998 | October Films | Comedy | $1,054,674 | 88,183 |
| 277 | Girl, Interrupted | Dec 21, 1999 | Sony Pictures | Drama | $1,023,687 | 85,592 |
| 278 | My Son the Fanatic | Jun 25, 1999 | Miramax | $1,008,329 | 84,308 | |
| 279 | Sarfarosh | Apr 30, 1999 | $1,007,590 | 84,247 | ||
| 280 | Just the Ticket | Feb 26, 1999 | MGM | $1,004,920 | 84,023 | |
| 281 | The Last Days | Feb 5, 1999 | October Films | Documentary | $988,259 | 82,630 |
| 282 | Steam: The Turkish Bath | Nov 25, 1998 | Strand Releasing | Drama | $964,609 | 80,653 |
| 283 | The Loss of Sexual Innocence | May 28, 1999 | Sony Pictures | Drama | $941,245 | 78,699 |
| 284 | Home Fries | Nov 25, 1998 | Warner Bros. | Black Comedy | $925,615 | 77,393 |
| 285 | Open Your Eyes | Apr 16, 1999 | Artisan | Drama | $872,797 | 72,976 |
| 286 | The Minus Man | Sep 10, 1999 | Artisan | Drama | $872,675 | 72,966 |
| 287 | Head On | Aug 13, 1999 | Strand Releasing | $861,252 | 72,011 | |
| 288 | The Nutcracker | Nov 25, 1998 | Musical | $836,908 | 69,975 | |
| 289 | Crna macka, beli macor | Sep 10, 1999 | USA Films | Comedy | $820,861 | 68,634 |
| 290 | My Name is Joe | Jan 22, 1999 | Artisan | $816,237 | 68,247 | |
| 291 | Vampires | Oct 30, 1998 | Sony Pictures | Horror | $768,399 | 64,247 |
| 292 | Les Enfants du Marais | Oct 1, 1999 | Drama | $762,817 | 63,781 | |
| 293 | La Grande Illusion | Sep 12, 1938 | Rialto Pictures | Drama | $744,086 | 62,215 |
| 294 | Grey Owl | Oct 1, 1999 | $740,449 | 61,910 | ||
| 295 | Hindustan Ki Kasam | Jul 23, 1999 | Action | $730,619 | 61,089 | |
| 296 | Metroland | Apr 9, 1999 | Sony Pictures | $715,502 | 59,825 | |
| 297 | SLC Punk! | Apr 16, 1999 | Sony Pictures Cla… | $695,933 | 58,188 | |
| 298 | Simon Sez | Sep 24, 1999 | $687,822 | 57,510 | ||
| 299 | Dil Kya Kare | Sep 24, 1999 | Eros Entertainment | Musical | $670,645 | 56,074 |
| 300 | Splendor | Sep 17, 1999 | Goldwyn Entertain… | Romantic Comedy | $668,910 | 55,929 |
| 301 | Living Out Loud | Oct 30, 1998 | New Line | Drama | $651,340 | 54,460 |
| 302 | The Legend of 1900 | Oct 29, 1999 | Fine Line | Musical | $619,031 | 51,758 |
| 303 | Twice Upon a Yesterday | May 28, 1999 | Trimark | Comedy | $608,510 | 50,879 |
| 304 | Hello Brother | Sep 10, 1999 | Video Sound | Action | $576,891 | 48,235 |
| 305 | Dog Park | Sep 24, 1999 | New Line | $569,967 | 47,656 | |
| 306 | Dancemaker | Mar 5, 1999 | Artistic License | Documentary | $566,249 | 47,345 |
| 307 | A Place Called Chiapas | Apr 9, 1999 | Documentary | $559,810 | 46,807 | |
| 308 | Happiness | Oct 16, 1998 | Good Machine Rele… | Black Comedy | $554,977 | 46,403 |
| 309 | Ladri di biciclette | Dec 12, 1949 | Drama | $545,960 | 45,649 | |
| 310 | One Man's Hero | Sep 24, 1999 | MGM | Action | $539,874 | 45,140 |
| 311 | Endurance | May 14, 1999 | Walt Disney | $539,443 | 45,104 | |
| 312 | Babar: King of the Elephants | Feb 26, 1999 | Adventure | $535,314 | 44,759 | |
| 313 | West Beirut | Sep 3, 1999 | Cowboy Pictures | Drama | $515,992 | 43,143 |
| 314 | Hote Hote Pyar Ho Gaya | Jul 2, 1999 | Action | $505,178 | 42,239 | |
| 315 | Beefcake | Oct 13, 1999 | Strand Releasing | Drama | $501,863 | 41,962 |
| 316 | Last Night | Oct 23, 1998 | Drama | $488,608 | 40,853 | |
| 317 | Practical Magic | Oct 16, 1998 | Warner Bros. | Comedy | $485,953 | 40,631 |
| 318 | Rien ne va plus | Oct 24, 1997 | New Yorker | Comedy | $482,311 | 40,327 |
| 319 | Rosetta | Nov 5, 1999 | USA Films | Drama | $463,323 | 38,739 |
| 320 | I'll Be Home For Christmas | Nov 13, 1998 | Walt Disney | Comedy | $443,584 | 37,089 |
| 321 | Angela's Ashes | Dec 24, 1999 | Paramount Pictures | Drama | $437,981 | 36,620 |
| 322 | Belly | Nov 4, 1998 | Artisan | Drama | $424,912 | 35,528 |
| 323 | Revelation | May 7, 1999 | $422,932 | 35,362 | ||
| 324 | Breakfast of Champions | Sep 17, 1999 | Walt Disney | Comedy | $419,747 | 35,096 |
| 325 | Sugar Town | Sep 17, 1999 | October Films | Comedy | $419,295 | 35,058 |
| 326 | Jing ke ci qin wang | Dec 17, 1999 | Sony Pictures Cla… | Drama | $407,483 | 34,070 |
| 327 | The Source | Aug 25, 1999 | WinStar Cinema | Documentary | $394,993 | 33,026 |
| 328 | Train of Life | Nov 5, 1999 | Paramount Pictures | Drama | $375,052 | 31,359 |
| 329 | Mast | Oct 15, 1999 | Eros Entertainment | Drama | $374,169 | 31,285 |
| 330 | Topsy Turvy | Dec 17, 1999 | USA Films | Musical | $373,623 | 31,239 |
| 331 | Stop Making Sense | Oct 19, 1984 | Cinecom | Concert/Performance | $349,484 | 29,221 |
| 332 | Snow Falling on Cedars | Dec 24, 1999 | Universal | Drama | $336,916 | 28,170 |
| 333 | The Acid House | Aug 6, 1999 | Zeitgeist | Drama | $336,158 | 28,107 |
| 334 | Dry Cleaning | Feb 5, 1999 | Strand Releasing | $335,170 | 28,024 | |
| 335 | Silsila Hai Pyar Ka | Apr 16, 1999 | Romantic Comedy | $333,204 | 27,860 | |
| 336 | Histoires d'hiver | Feb 26, 1999 | $325,865 | 27,246 | ||
| 337 | The Hi-Lo Country | Dec 30, 1998 | Gramercy | $324,457 | 27,129 | |
| 338 | Matroni et Moi | Oct 8, 1999 | Comedy | $307,410 | 25,703 | |
| 339 | Pariah | Feb 19, 1999 | Indican Pictures | Action | $301,507 | 25,210 |
| 340 | La ciudad | Oct 22, 1999 | Zeitgeist | Drama | $294,988 | 24,664 |
| 341 | Tour Truffaut | Apr 23, 1999 | $278,348 | 23,273 | ||
| 342 | The Lovers on the Bridge | Jul 2, 1999 | Miramax | Drama | $276,796 | 23,144 |
| 343 | Sib | Feb 19, 1999 | Drama | $274,887 | 22,984 | |
| 344 | Unconditional Love | Feb 12, 1999 | Action | $271,224 | 22,678 | |
| 345 | Perfect Blue | Aug 20, 1999 | Manga Entertainme… | Drama | $263,685 | 22,047 |
| 346 | The 24 Hour Woman | Jan 29, 1999 | Artisan | Comedy | $256,970 | 21,486 |
| 347 | Bure baruta | Jul 23, 1999 | Paramount Vantage | Drama | $254,510 | 21,280 |
| 348 | Eternity and a Day | May 28, 1999 | Artistic License | Drama | $250,703 | 20,962 |
| 349 | The Wizard of Oz | Aug 25, 1939 | Warner Bros. | Musical | $239,638 | 20,037 |
| 350 | Show Me Love | Oct 15, 1999 | Strand Releasing | Drama | $236,782 | 19,797 |
| 351 | Friends and Lovers | Apr 16, 1999 | Lionsgate | Drama | $235,694 | 19,707 |
| 352 | The Adventures of Sebastian C… | Aug 6, 1999 | Paramount Vantage | Comedy | $235,530 | 19,693 |
| 353 | Desert Blue | Jun 4, 1999 | Goldwyn Entertain… | $233,425 | 19,517 | |
| 354 | Sunshine | Dec 17, 1999 | Paramount Vantage | Drama | $229,964 | 19,227 |
| 355 | The Very Thought of You | Aug 27, 1999 | Miramax | Romantic Comedy | $221,721 | 18,539 |
| 356 | Such a Long Journey | Feb 25, 1999 | Shooting Gallery | $217,938 | 18,222 | |
| 357 | Caligula | Feb 1, 1980 | Drama | $217,069 | 18,149 | |
| 358 | Ronin | Sep 25, 1998 | MGM | Action | $208,339 | 17,420 |
| 359 | The Saragossa Manuscript | May 21, 1999 | Cowboy Pictures | Comedy | $205,811 | 17,208 |
| 360 | Beloved | Oct 16, 1998 | Walt Disney | Horror | $205,029 | 17,143 |
| 361 | Titus | Dec 24, 1999 | 20th Century Fox | Drama | $203,245 | 16,993 |
| 362 | Peeping Tom | Feb 5, 1999 | Thriller/Suspense | $197,663 | 16,527 | |
| 363 | Lal Baadshah | Mar 5, 1999 | Action | $192,756 | 16,117 | |
| 364 | Vaastar | Oct 15, 1999 | Action | $191,565 | 16,017 | |
| 365 | Julien Donkey-Boy | Oct 8, 1999 | Fine Line | $188,879 | 15,793 | |
| 366 | Thicker Than Water | Oct 27, 1999 | Palm Pictures | Drama | $187,930 | 15,713 |
| 367 | Dr. Akagi | Jan 15, 1999 | Kino International | $169,116 | 14,140 | |
| 368 | Kohram | Aug 6, 1999 | Video Sound | Action | $165,408 | 13,830 |
| 369 | Stiff Upper Lips | Aug 27, 1999 | Cowboy Pictures | Comedy | $163,819 | 13,697 |
| 370 | Late August, Early September | Jul 9, 1999 | Zeitgeist | Drama | $160,579 | 13,426 |
| 371 | Very Bad Things | Nov 25, 1998 | Polygram | Black Comedy | $155,473 | 12,999 |
| 372 | Holy Smoke | Dec 3, 1999 | Miramax | Drama | $153,804 | 12,860 |
| 373 | Among Giants | Mar 26, 1999 | Fox Searchlight | Romantic Comedy | $151,522 | 12,669 |
| 374 | The Joyriders | Apr 16, 1999 | Drama | $150,908 | 12,618 | |
| 375 | Dahek: A Burning Passion | Dec 17, 1999 | $150,409 | 12,576 | ||
| 376 | Those Who Love Me Can Take th… | Aug 4, 1999 | Kino International | Drama | $149,856 | 12,530 |
| 377 | Bride of Chucky | Oct 16, 1998 | Universal | Horror | $149,641 | 12,512 |
| 378 | Joe the King | Oct 15, 1999 | Trimark | $141,917 | 11,866 | |
| 379 | The Mirror | Nov 25, 1998 | $136,099 | 11,380 | ||
| 380 | The War Zone | Dec 10, 1999 | Lot 47 Films | Drama | $134,882 | 11,278 |
| 381 | Seul contre tous | Mar 17, 1999 | Strand Releasing | Drama | $133,837 | 11,190 |
| 382 | Ever After: A Cinderella Story | Jul 31, 1998 | 20th Century Fox | Drama | $133,149 | 11,133 |
| 383 | The Mask of Zorro | Jul 17, 1998 | Sony Pictures | Adventure | $131,395 | 10,986 |
| 384 | God Said, 'Ha!' | Feb 12, 1999 | Miramax | $123,188 | 10,300 | |
| 385 | Meeting People is Easy | Mar 26, 1999 | Seventh Art Relea… | Documentary | $120,735 | 10,095 |
| 386 | Sirf Tum | Jun 11, 1999 | Eros Entertainment | Drama | $119,565 | 9,997 |
| 387 | 8 1/2 | Jun 25, 1963 | Kino Lorber | Drama | $119,341 | 9,978 |
| 388 | Six Ways to Sunday | Mar 5, 1999 | Stratosphere Ente… | $118,503 | 9,908 | |
| 389 | Leila | May 14, 1999 | First Run Features | Drama | $118,030 | 9,869 |
| 390 | El Abuelo | Oct 8, 1999 | Miramax | Drama | $117,804 | 9,850 |
| 391 | Grizzly Falls | Oct 8, 1999 | Adventure | $113,891 | 9,523 | |
| 392 | Just a Little Harmless Sex | Jun 11, 1999 | Phaedra Cinema | $108,843 | 9,101 | |
| 393 | The Ogre | Dec 11, 1998 | Kino International | $107,513 | 8,989 | |
| 394 | Following | Apr 2, 1999 | Zeitgeist | Thriller/Suspense | $105,250 | 8,800 |
| 395 | Virtual Sexuality | Dec 3, 1999 | Sony Pictures | Romantic Comedy | $103,273 | 8,635 |
| 396 | Get Bruce | Sep 17, 1999 | Miramax | Documentary | $101,601 | 8,495 |
| 397 | The Third Miracle | Dec 29, 1999 | Sony Pictures | Drama | $97,820 | 8,178 |
| 398 | On The Ropes | Aug 18, 1999 | $96,370 | 8,058 | ||
| 399 | The Theory of Flight | Dec 23, 1998 | Fine Line | $94,912 | 7,936 | |
| 400 | L'Ennui | Oct 8, 1999 | Phaedra Cinema | Drama | $86,324 | 7,218 |
| 401 | The Eel (うなぎ) | Aug 21, 1998 | New Yorker | Comedy | $85,806 | 7,174 |
| 402 | Whiteboyz | Sep 10, 1999 | Fox Searchlight | Drama | $84,815 | 7,092 |
| 403 | B. Monkey | Sep 10, 1999 | Miramax | Thriller/Suspense | $81,281 | 6,796 |
| 404 | The Velocity of Gary | Jul 16, 1999 | Sony Pictures | $80,389 | 6,721 | |
| 405 | Mr. Death: The Rise and Fall … | Dec 29, 1999 | Lionsgate | Documentary | $78,908 | 6,597 |
| 406 | Man of the Century | Oct 29, 1999 | Fine Line | $77,766 | 6,502 | |
| 407 | Shiloh 2: Shiloh Season | Jun 25, 1999 | Warner Bros. | $77,693 | 6,496 | |
| 408 | Genghis Blues | Jul 9, 1999 | Roxie Releasing | Documentary | $76,765 | 6,419 |
| 409 | Mein Liebster Feind | Nov 5, 1999 | New Yorker | Documentary | $74,067 | 6,193 |
| 410 | Al di là delle nuvole | Dec 3, 1999 | Drama | $72,725 | 6,081 | |
| 411 | Free Enterprise | Jun 4, 1999 | Regent Releasing | $71,084 | 5,944 | |
| 412 | Same Old Song | Oct 15, 1999 | Artistic License | $66,279 | 5,542 | |
| 413 | Finding North | Jun 4, 1999 | Cowboy Pictures | Romantic Comedy | $63,353 | 5,297 |
| 414 | Eight Days a Week | Feb 26, 1999 | Legacy Releasing | $62,030 | 5,186 | |
| 415 | Let it Come Down: The Life of… | Apr 28, 1999 | Zeitgeist | Documentary | $62,004 | 5,184 |
| 416 | La Cucaracha | Apr 23, 1999 | Drama | $61,862 | 5,172 | |
| 417 | Best Laid Plans | Sep 10, 1999 | 20th Century Fox | Thriller/Suspense | $60,391 | 5,049 |
| 418 | Like It Is | Aug 28, 1998 | First Run Features | $60,075 | 5,023 | |
| 419 | Touch of Evil | May 21, 1958 | October Films | Thriller/Suspense | $57,709 | 4,825 |
| 420 | Apt Pupil | Oct 23, 1998 | Sony/TriStar | Thriller/Suspense | $57,497 | 4,807 |
| 421 | Bandits | Sep 24, 1999 | Stratosphere Ente… | Drama | $56,944 | 4,761 |
| 422 | Celebrity | Nov 20, 1998 | Miramax | Comedy | $55,127 | 4,609 |
| 423 | All the Little Animals | Sep 3, 1999 | Lionsgate | Thriller/Suspense | $54,971 | 4,596 |
| 424 | Regret to Inform | Jun 25, 1999 | Artistic License | Documentary | $53,271 | 4,454 |
| 425 | Love is the Devil | Oct 7, 1998 | Strand Releasing | Drama | $52,808 | 4,415 |
| 426 | Shattered Image | Dec 4, 1998 | Lionsgate | $50,458 | 4,219 | |
| 427 | A Map of the World | Dec 3, 1999 | USA Films | Drama | $49,154 | 4,110 |
| 428 | New Rose Hotel | Oct 1, 1999 | Avalanche Releasi… | Drama | $48,066 | 4,019 |
| 429 | Hard | Jun 25, 1999 | $46,135 | 3,857 | ||
| 430 | That's the Way I Like It | Oct 15, 1999 | Miramax | $45,483 | 3,803 | |
| 431 | Meishaonian zhi lian | Mar 19, 1999 | Drama | $43,859 | 3,667 | |
| 432 | The Sticky Fingers of Time | Jan 8, 1999 | Strand Releasing | Thriller/Suspense | $42,837 | 3,582 |
| 433 | Molly | Oct 22, 1999 | MGM | Drama | $40,956 | 3,424 |
| 434 | Mighty Peking Man | Apr 23, 1999 | Horror | $39,449 | 3,298 | |
| 435 | 2by4 | Nov 26, 1999 | Strand Releasing | Drama | $39,169 | 3,275 |
| 436 | Doctor Dolittle | Jun 26, 1998 | 20th Century Fox | Comedy | $38,799 | 3,244 |
| 437 | Bedrooms and Hallways | Sep 3, 1999 | First Run Features | Comedy | $38,750 | 3,240 |
| 438 | My Dinner with Andre | Jan 1, 1981 | New Yorker | Comedy | $35,463 | 2,965 |
| 439 | 42 Up | Nov 17, 1999 | First Run Features | Documentary | $34,317 | 2,869 |
| 440 | Jeanne and the Perfect Guy | Apr 16, 1999 | Strand Releasing | Musical | $32,810 | 2,743 |
| 441 | Blood, Guts, Bullets and Octa… | Jan 15, 1999 | Lionsgate | Comedy | $32,193 | 2,692 |
| 442 | Broken Vessels | Jul 2, 1999 | Drama | $31,767 | 2,656 | |
| 443 | The Cruise | Oct 23, 1998 | Artisan | Documentary | $31,647 | 2,646 |
| 444 | Miss Julie | Dec 10, 1999 | MGM | Drama | $30,858 | 2,580 |
| 445 | How Stella Got Her Groove Back | Aug 14, 1998 | 20th Century Fox | Drama | $30,573 | 2,556 |
| 446 | Diamonds | Dec 10, 1999 | Miramax | Comedy | $30,359 | 2,538 |
| 447 | A Night at the Roxbury | Oct 2, 1998 | Paramount Pictures | Comedy | $30,138 | 2,520 |
| 448 | I'm Losing You | Jul 16, 1999 | Lionsgate | $29,872 | 2,498 | |
| 449 | Clubland | Apr 16, 1999 | Legacy Releasing | $29,660 | 2,480 | |
| 450 | Dial M for Murder | May 29, 1954 | Thriller/Suspense | $29,575 | 2,472 | |
| 451 | Some Fish Can Fly | Nov 5, 1999 | Artistic License | Romantic Comedy | $29,427 | 2,460 |
| 452 | Frogs for Snakes | May 21, 1999 | Artisan | $28,702 | 2,400 | |
| 453 | Existo | Sep 17, 1999 | Comedy | $28,664 | 2,397 | |
| 454 | Women | Sep 17, 1999 | $27,593 | 2,307 | ||
| 455 | Welcome Back Mr. McDonald | Sep 8, 1999 | Comedy | $27,091 | 2,265 | |
| 456 | Pizzicata | Feb 5, 1999 | $26,722 | 2,234 | ||
| 457 | Spanish Fly | Dec 2, 1999 | Miramax | $26,244 | 2,194 | |
| 458 | The Empty Mirror | Mar 19, 1999 | Lionsgate | $25,309 | 2,116 | |
| 459 | Naturally Native | Oct 8, 1999 | $24,739 | 2,069 | ||
| 460 | The Imposters | Oct 2, 1998 | Fox Searchlight | Comedy | $23,892 | 1,998 |
| 461 | Marcello Mastroianni - I Reme… | Aug 13, 1999 | First Look | Documentary | $23,141 | 1,935 |
| 462 | Rosie | Jul 23, 1999 | New Yorker | $22,552 | 1,886 | |
| 463 | Beyond the Mat | Oct 22, 1999 | Universal | Documentary | $22,441 | 1,876 |
| 464 | The Gambler | Aug 4, 1999 | Drama | $21,502 | 1,798 | |
| 465 | Hell's Kitchen | Dec 3, 1999 | Cowboy Pictures | $21,476 | 1,796 | |
| 466 | Onegin | Dec 17, 1999 | Goldwyn Entertain… | $20,848 | 1,743 | |
| 467 | Simpatico | Dec 17, 1999 | Phaedra Cinema | Comedy | $20,845 | 1,743 |
| 468 | The Thief | Jul 17, 1998 | Stratosphere Ente… | Drama | $20,829 | 1,742 |
| 469 | Private Confessions | Jan 6, 1999 | Kino International | $20,622 | 1,724 | |
| 470 | The Inheritors | Oct 9, 1998 | Stratosphere Ente… | $20,205 | 1,689 | |
| 471 | No | Apr 23, 1999 | New Yorker | $19,729 | 1,650 | |
| 472 | Fest of the Best | Oct 22, 1999 | $18,625 | 1,557 | ||
| 473 | Six-String Samurai | Sep 18, 1998 | Palm Pictures | $18,604 | 1,556 | |
| 474 | Dreaming of Joseph Lees | Oct 29, 1999 | Fox Searchlight | $18,081 | 1,512 | |
| 475 | Raising the Stakes | Aug 20, 1999 | $16,692 | 1,396 | ||
| 476 | Gadjo Dilo | Aug 7, 1998 | Lionsgate | Drama | $16,537 | 1,383 |
| 477 | Les Bonnes Femmes | Aug 13, 1999 | Drama | $15,487 | 1,295 | |
| 478 | Red Dwarf | Jun 18, 1999 | Goldwyn Entertain… | Comedy | $15,301 | 1,279 |
| 479 | Agnes Browne | Dec 3, 1999 | USA Films | Comedy | $14,884 | 1,244 |
| 480 | The Silence | Nov 10, 1999 | New Yorker | Drama | $14,225 | 1,189 |
| 481 | Where\'s Marlowe? | Nov 12, 1999 | Paramount Vantage | Comedy | $14,091 | 1,178 |
| 482 | The Underground | Mar 31, 1999 | Action | $13,676 | 1,144 | |
| 483 | The Suburbans | Oct 29, 1999 | Sony Pictures | $13,648 | 1,141 | |
| 484 | The Last Cigarette | Jun 9, 1999 | New Yorker | Documentary | $13,358 | 1,117 |
| 485 | Taxman | Sep 17, 1999 | Comedy | $13,321 | 1,114 | |
| 486 | Floating | Sep 3, 1999 | Phaedra Cinema | Drama | $13,304 | 1,112 |
| 487 | The Winners | Jan 20, 1999 | First Run Features | Documentary | $12,968 | 1,084 |
| 488 | Sparkler | Mar 19, 1999 | Strand Releasing | $12,935 | 1,081 | |
| 489 | At Sachem Farm | Jun 5, 1999 | Distributor Unkno… | Drama | $11,772 | 984 |
| 490 | Getting to Know You | Jan 22, 1999 | $11,772 | 984 | ||
| 491 | Giving It Up | Jan 17, 1999 | Lionsgate | Romantic Comedy | $11,772 | 984 |
| 492 | Harvest | Mar 12, 1999 | $11,772 | 984 | ||
| 493 | Ayn Rand: A Sense of Life | Feb 13, 1998 | Strand Releasing | Documentary | $11,152 | 932 |
| 494 | The Mating Habits of the Eart… | Oct 8, 1999 | $10,910 | 912 | ||
| 495 | Modulations | Sep 4, 1998 | Strand Releasing | $10,839 | 906 | |
| 496 | Five Wives, Three Secretaries… | Oct 8, 1999 | Castle Hill Produ… | Documentary | $10,477 | 876 |
| 497 | Pusher | May 7, 1999 | First Run Features | $10,453 | 874 | |
| 498 | Men Cry Bullets | Oct 8, 1999 | Phaedra Cinema | $9,653 | 807 | |
| 499 | And Baby Makes 2 | Jun 25, 1999 | First Run Features | Documentary | $9,554 | 799 |
| 500 | A Moment of Innocence | Nov 10, 1999 | New Yorker | $9,410 | 787 | |
| 501 | Portraits Chinois | Nov 5, 1999 | Phaedra Cinema | $9,351 | 782 | |
| 502 | Suits | Sep 24, 1999 | $8,655 | 724 | ||
| 503 | The Day of the Beast | Dec 23, 1998 | Trimark | Action | $8,377 | 700 |
| 504 | The Governess | Jul 31, 1998 | Sony Pictures Cla… | Drama | $8,080 | 676 |
| 505 | Play it to the Bone | Dec 24, 1999 | Walt Disney | Comedy | $7,925 | 662 |
| 506 | Strawberry Fields | Jun 4, 1999 | Phaedra Cinema | Drama | $7,880 | 659 |
| 507 | Iris Blonde | May 14, 1999 | Miramax | Romantic Comedy | $7,776 | 650 |
| 508 | East Palace West Palace | Jul 24, 1998 | Strand Releasing | $7,699 | 644 | |
| 509 | When Love Comes | Jun 25, 1999 | Drama | $7,633 | 638 | |
| 510 | Tinseltown | Jan 22, 1999 | MGM | Comedy | $7,461 | 624 |
| 511 | Western | Jul 24, 1998 | New Yorker | $7,355 | 615 | |
| 512 | The Boys | Oct 15, 1999 | Stratosphere Ente… | Drama | $6,898 | 577 |
| 513 | Close-Up | Dec 31, 1999 | $6,286 | 525 | ||
| 514 | Slaves of Hollywood | Oct 29, 1999 | Comedy | $6,234 | 521 | |
| 515 | Fever Pitch | Sep 24, 1999 | Phaedra Cinema | Romantic Comedy | $5,931 | 496 |
| 516 | Jerome | Dec 10, 1999 | Phaedra Cinema | $5,886 | 492 | |
| 517 | Hard Core Logo | Nov 13, 1998 | Miramax | Comedy | $5,820 | 487 |
| 518 | A Girl Called Rose Marie | Oct 15, 1999 | Castle Hill Produ… | Drama | $5,601 | 468 |
| 519 | Heaven | Apr 30, 1999 | Miramax | Thriller/Suspense | $4,669 | 390 |
| 520 | Pink Narcissus | Dec 24, 1999 | Drama | $4,059 | 339 | |
| 521 | Young and Dangerous, Parts I … | Jul 23, 1999 | Action | $3,823 | 320 | |
| 522 | Virtue | Feb 5, 1999 | Margin Films | Comedy | $3,685 | 308 |
| 523 | Sixth Happiness | Nov 5, 1999 | Regent Releasing | Drama | $3,626 | 303 |
| 524 | Terror Firmer | Oct 29, 1999 | $3,376 | 282 | ||
| 525 | Lilian's Story | Mar 26, 1999 | Phaedra Cinema | Drama | $2,872 | 240 |
| 526 | Wallowitch & Ross: This Moment | Dec 10, 1999 | First Run Features | $2,696 | 225 | |
| 527 | The Milky Way | Jan 22, 1999 | Kino International | $2,585 | 216 | |
| 528 | Flushed | Aug 13, 1999 | $2,201 | 184 | ||
| 529 | The Underground Comedy Movie | May 14, 1999 | Phaedra Cinema | Comedy | $2,015 | 169 |
| 530 | It’s in the Water | Jan 30, 1998 | Romantic Comedy | $1,907 | 159 | |
| 531 | Olympia | May 21, 1999 | Drama | $1,507 | 126 | |
| 532 | Summerspell | Jul 2, 1999 | Drama | $1,420 | 119 | |
| 533 | The Last Big Thing | Sep 25, 1998 | Stratosphere Ente… | $598 | 50 |