| Rank | Release
| Genre
| Budget
| Running Time
| Gross | Theaters | Total Gross | Release Date | Distributor
| Estimated
|
|---|
| 1 | The Matrix | - | - | - | $118,634,201 | 2,903 | $171,479,930 | Mar 31 | Warner Bros. | false |
| 2 | Life | - | - | - | $40,930,685 | 2,613 | $64,016,268 | Apr 16 | Universal Pictures | false |
| 3 | Never Been Kissed | - | - | - | $33,152,390 | 2,500 | $55,474,756 | Apr 9 | Twentieth Century Fox | false |
| 4 | 10 Things I Hate About You | - | - | - | $26,901,524 | 2,311 | $38,178,166 | Mar 31 | Walt Disney Studios Motion Pictures | false |
| 5 | Analyze This | - | - | - | $26,140,399 | 2,537 | $106,885,658 | Mar 5 | Warner Bros. | false |
| 6 | The Out-of-Towners | - | - | - | $24,070,744 | 2,128 | $28,544,120 | Apr 2 | Paramount Pictures | false |
| 7 | Forces of Nature | - | - | - | $20,350,684 | 2,335 | $52,900,680 | Mar 19 | DreamWorks Distribution | false |
| 8 | Go | - | - | - | $13,466,630 | 1,563 | $16,943,454 | Apr 9 | Sony Pictures Releasing | false |
| 9 | Edtv | - | - | - | $12,098,687 | 2,631 | $22,431,897 | Mar 26 | Universal Pictures | false |
| 10 | Shakespeare in Love | - | - | - | $12,086,403 | 2,030 | $100,317,794 | Dec 11 | Miramax | false |
| 11 | Doug's 1st Movie | - | - | - | $11,786,091 | 2,268 | $19,440,089 | Mar 26 | Walt Disney Studios Motion Pictures | false |
| 12 | Life Is Beautiful | - | - | - | $11,014,138 | 1,136 | $57,247,384 | Oct 23 | Miramax | false |
| 13 | Baby Geniuses | - | - | - | $7,852,066 | 1,702 | $27,250,736 | Mar 12 | Sony Pictures Releasing | false |
| 14 | Twin Dragons | - | - | - | $6,562,672 | 1,131 | $8,359,717 | Apr 9 | Miramax | false |
| 15 | The Mod Squad | - | - | - | $6,252,633 | 2,290 | $13,263,993 | Mar 26 | Metro-Goldwyn-Mayer (MGM) | false |
| 16 | Cookie's Fortune | - | - | - | $5,743,848 | 559 | $10,920,544 | Apr 2 | October Films | false |
| 17 | True Crime | - | - | - | $5,298,779 | 1,852 | $16,649,768 | Mar 19 | Warner Bros. | false |
| 18 | Pushing Tin | - | - | - | $4,845,534 | 1,284 | $8,408,835 | Apr 23 | Twentieth Century Fox | false |
| 19 | Foolish | - | - | - | $4,379,435 | 410 | $6,033,999 | Apr 9 | Artisan Entertainment | false |
| 20 | Lost & Found | - | - | - | $3,981,896 | 2,469 | $6,552,255 | Apr 23 | Warner Bros. | false |
| 21 | October Sky | - | - | - | $3,769,862 | 1,702 | $32,570,685 | Feb 19 | Universal Pictures | false |
| 22 | Entrapment | - | - | - | $3,732,290 | 2,879 | $87,704,396 | Apr 30 | Twentieth Century Fox | false |
| 23 | The King and I | - | - | - | $3,651,364 | 2,352 | $11,993,021 | Mar 19 | Warner Bros. | false |
| 24 | Saving Private Ryan | - | - | - | $3,230,715 | 2,807 | $216,540,909 | Jul 24 | DreamWorks Distribution | false |
| 25 | Cruel Intentions | - | - | - | $3,178,735 | 2,312 | $38,328,567 | Mar 5 | Sony Pictures Releasing | false |
| 26 | T-Rex: Back to the Cretaceous | - | - | - | $2,548,399 | 38 | $53,354,743 | Oct 23 | IMAX | false |
| 27 | A Walk on the Moon | - | - | - | $2,026,663 | 246 | $4,750,660 | Mar 26 | Miramax | false |
| 28 | A Bug's Life | - | - | - | $1,931,679 | 2,773 | $162,798,565 | Nov 20 | Walt Disney Studios Motion Pictures | false |
| 29 | The Prince of Egypt | - | - | - | $1,875,108 | 3,218 | $101,413,188 | Dec 18 | DreamWorks Distribution | false |
| 30 | The Rage: Carrie 2 | - | - | - | $1,863,503 | 2,286 | $17,762,705 | Mar 12 | Metro-Goldwyn-Mayer (MGM) | false |
| 31 | Goodbye Lover | - | - | - | $1,797,836 | 865 | $1,940,299 | Apr 16 | Warner Bros. | false |
| 32 | Mysteries of Egypt | - | - | - | $1,761,430 | 27 | $40,593,486 | Aug 21 | IMAX | false |
| 33 | Everest | - | - | - | $1,661,677 | 62 | $87,178,599 | Mar 6 | MacGillivray Freeman Films | false |
| 34 | The Other Sister | - | - | - | $1,425,331 | 1,863 | $27,807,627 | Feb 26 | Walt Disney Studios Motion Pictures | false |
| 35 | The Corruptor | - | - | - | $1,370,446 | 1,804 | $15,164,492 | Mar 12 | New Line Cinema | false |
| 36 | eXistenZ | - | - | - | $1,346,299 | 256 | $2,856,712 | Apr 23 | Miramax | false |
| 37 | Patch Adams | - | - | - | $1,333,765 | 2,909 | $135,026,902 | Dec 25 | Universal Pictures | false |
| 38 | Message in a Bottle | - | - | - | $1,329,237 | 2,545 | $52,880,016 | Feb 12 | Warner Bros. | false |
| 39 | Elizabeth | - | - | - | $1,225,875 | 624 | $30,082,699 | Nov 6 | Gramercy Pictures (I) | false |
| 40 | You've Got Mail | - | - | - | $1,098,924 | 2,948 | $115,821,495 | Dec 18 | Warner Bros. | false |
| 41 | Lock, Stock and Two Smoking Barrels | - | - | - | $1,088,469 | 161 | $3,753,929 | Mar 5 | Gramercy Pictures (I) | false |
| 42 | Payback | - | - | - | $1,050,368 | 2,855 | $81,526,121 | Feb 5 | Paramount Pictures | false |
| 43 | The Deep End of the Ocean | - | - | - | $1,046,549 | 1,907 | $13,898,649 | Mar 12 | Sony Pictures Releasing | false |
| 44 | Affliction | - | - | - | $949,475 | 335 | $6,330,054 | Dec 30 | Lionsgate Films | false |
| 45 | Tango | - | - | - | $933,668 | 63 | $1,897,948 | Jan 22 | Sony Pictures Classics | false |
| 46 | Gods and Monsters | - | - | - | $931,003 | 149 | $6,451,628 | Nov 6 | Lionsgate Films | false |
| 47 | Wing Commander | - | - | - | $906,011 | 2,019 | $11,578,059 | Mar 12 | Twentieth Century Fox | false |
| 48 | Blast from the Past | - | - | - | $870,257 | 2,544 | $26,511,114 | Feb 12 | New Line Cinema | false |
| 49 | The Faculty | - | - | - | $821,764 | 2,365 | $40,283,321 | Dec 25 | Miramax | false |
| 50 | Central Station | - | - | - | $814,580 | 144 | $5,969,553 | Nov 20 | Sony Pictures Classics | false |
| 51 | 8MM | - | - | - | $767,157 | 2,370 | $36,663,315 | Feb 26 | Sony Pictures Releasing | false |
| 52 | A Civil Action | - | - | - | $722,020 | 2,319 | $56,709,981 | Dec 25 | Walt Disney Studios Motion Pictures | false |
| 53 | Waking Ned Devine | - | - | - | $694,794 | 540 | $24,792,251 | Nov 20 | - | false |
| 54 | Rushmore | - | - | - | $633,093 | 830 | $17,105,219 | Dec 11 | Walt Disney Studios Motion Pictures | false |
| 55 | Stepmom | - | - | - | $623,839 | 2,503 | $91,137,662 | Dec 25 | Sony Pictures Releasing | false |
| 56 | Africa's Elephant Kingdom | - | - | - | $621,260 | 15 | $13,485,455 | May 1 | IMAX | false |
| 57 | The Dreamlife of Angels | - | - | - | $559,041 | 66 | $1,726,567 | Apr 2 | Sony Pictures Classics | false |
| 58 | Hideous Kinky | - | - | - | $435,175 | 78 | $1,263,279 | Apr 16 | - | false |
| 59 | My Favorite Martian | - | - | - | $412,572 | 2,349 | $36,850,101 | Feb 12 | Walt Disney Studios Motion Pictures | false |
| 60 | Encounter in the Third Dimension | - | - | - | $381,467 | 16 | $7,195,792 | Feb 26 | - | false |
| 61 | Varsity Blues | - | - | - | $350,295 | 2,364 | $52,894,169 | Jan 15 | Paramount Pictures | false |
| 62 | Idle Hands | - | - | - | $329,023 | 1,611 | $4,152,230 | Apr 30 | Sony Pictures Releasing | false |
| 63 | The Thin Red Line | - | - | - | $312,392 | 1,657 | $36,400,491 | Dec 25 | Twentieth Century Fox | false |
| 64 | The Last Days | - | - | - | $306,050 | 32 | $421,432 | Feb 5 | October Films | false |
| 65 | SLC Punk! | - | - | - | $299,569 | 137 | $299,569 | Apr 16 | Sony Pictures Classics | false |
| 66 | Children of Heaven | - | - | - | $290,776 | 18 | $933,933 | Jan 22 | Miramax | false |
| 67 | The General | - | - | - | $273,935 | 41 | $1,214,198 | Dec 18 | Sony Pictures Classics | false |
| 68 | A Simple Plan | - | - | - | $270,428 | 675 | $16,316,273 | Dec 11 | Paramount Pictures | false |
| 69 | She's All That | - | - | - | $260,722 | 2,654 | $63,366,989 | Jan 29 | Miramax | false |
| 70 | Enemy of the State | - | - | - | $229,891 | 2,517 | $111,549,836 | Nov 20 | Walt Disney Studios Motion Pictures | false |
| 71 | Le dernier souffle | - | - | - | $226,765 | 33 | $316,043 | Mar 26 | Lionsgate Films | false |
| 72 | Election | - | - | - | $225,003 | 827 | $14,902,041 | Apr 23 | Paramount Pictures | false |
| 73 | The Waterboy | - | - | - | $222,557 | 2,782 | $161,491,646 | Nov 6 | Walt Disney Studios Motion Pictures | false |
| 74 | Hilary and Jackie | - | - | - | $209,159 | 300 | $4,912,892 | Dec 30 | October Films | false |
| 75 | Thrill Ride: The Science of Fun | - | - | - | $207,161 | 81 | $18,798,590 | Jul 11 | Sony Pictures Classics | false |
| 76 | 200 Cigarettes | - | - | - | $147,851 | 978 | $6,852,450 | Feb 26 | Paramount Pictures | false |
| 77 | Silsila Hai Pyar Ka | - | - | - | $141,528 | 19 | $141,528 | Apr 16 | Eros Worldwide | false |
| 78 | Extreme | - | - | - | $137,419 | 21 | $12,475,172 | Apr 2 | IMAX | false |
| 79 | The Rugrats Movie | - | - | - | $134,268 | 2,832 | $100,494,675 | Nov 20 | Paramount Pictures | false |
| 80 | Mighty Joe Young | - | - | - | $112,607 | 2,559 | $50,632,037 | Dec 25 | Walt Disney Studios Motion Pictures | false |
| 81 | 8½ 1999 Re-release | - | - | - | $98,760 | 1 | $98,760 | Apr 9 | Kino International | false |
| 82 | Open Your Eyes | - | - | - | $90,492 | 34 | $370,720 | Apr 16 | Artisan Entertainment | false |
| 83 | The Harmonists | - | - | - | $73,194 | 33 | $244,861 | Mar 12 | Miramax | false |
| 84 | Six Ways to Sunday | - | - | - | $41,490 | 6 | $54,751 | Mar 5 | - | false |
| 85 | Friends & Lovers | - | - | - | $33,543 | 53 | $33,543 | Apr 16 | Lionsgate Films | false |
| 86 | The Joyriders | - | - | - | $26,999 | 26 | $26,999 | Apr 16 | Providence Entertainment | false |
| 87 | Metroland | - | - | - | $26,682 | 12 | $26,682 | Apr 9 | Lionsgate Films | false |
| 88 | Sarfarosh | - | - | - | $26,405 | 24 | $288,733 | Apr 30 | Eros Worldwide | false |
| 89 | The Monster 1999 Re-release | - | - | - | $22,819 | 1 | $22,819 | Apr 2 | Lionsgate Films | false |
| 90 | Clubland | - | - | - | $18,529 | 60 | $18,529 | Apr 16 | - | false |
| 91 | The Winslow Boy | - | - | - | $15,751 | 141 | $3,957,934 | Apr 30 | Sony Pictures Classics | false |
| 92 | Blood, Guts, Bullets and Octane | - | - | - | $15,035 | 7 | $15,035 | Apr 9 | Lionsgate Films | false |
| 93 | La Cucaracha | - | - | - | $14,692 | 11 | $14,692 | Apr 23 | - | false |
| 94 | Dial M for Murder 1999 Re-release | - | - | - | $12,562 | 1 | $12,562 | Apr 9 | Warner Bros. | false |
| 95 | Get Real | - | - | - | $11,377 | 40 | $1,152,979 | Apr 30 | Paramount Classics | false |
| 96 | Tout Truffaut Film Festival | - | - | - | $11,206 | 1 | $11,206 | Apr 23 | WinStar Cinema | false |
| 97 | Lovers of the Arctic Circle | - | - | - | $10,697 | 23 | $317,422 | Apr 9 | Fine Line Features | false |
| 98 | Following | - | - | - | $10,375 | 2 | $48,482 | Apr 2 | Zeitgeist Films | false |
| 99 | Three Seasons | - | - | - | $10,150 | 66 | $2,021,698 | Apr 30 | October Films | false |
| 100 | Goliathon | - | - | - | $5,000 | 14 | $17,368 | Apr 23 | Cowboy Pictures | false |
| 101 | Nô | - | - | - | $4,868 | 2 | $4,868 | Apr 23 | New Yorker Films | false |
| 102 | Jeanne and the Perfect Guy | - | - | - | $4,417 | 1 | $4,417 | Apr 16 | Strand Releasing | false |
| 103 | Het ondergronds orkest | - | - | - | $4,315 | 1 | $4,315 | Apr 2 | First Look International | false |
| 104 | Do You Wanna Dance? | - | - | - | $3,210 | 1 | $3,210 | Apr 16 | - | false |
| 105 | The Velocity of Gary | - | - | - | $306 | 1 | $2,143 | Apr 30 | - | false |
