| Rank
| Release
| Genre
| Budget
| Running Time
| Gross | Max Theaters | Total Gross | % of Total | Release Date | Distributor
|
|---|
| 1 | Star Wars: Episode I - The Phantom Menace | - | - | - | $255,758,124 | 3,126 | $431,088,295 | 59.3% | May 19, 1999 | Twentieth Century Fox |
| 2 | The Mummy | - | - | - | $127,523,525 | 3,411 | $155,516,138 | 82% | May 7, 1999 | Universal Pictures |
| 3 | Notting Hill | - | - | - | $49,419,470 | 2,786 | $116,089,678 | 42.6% | May 28, 1999 | Universal Pictures |
| 4 | Entrapment | - | - | - | $47,437,975 | 2,879 | $87,704,396 | 54.1% | Apr 30, 1999 | Twentieth Century Fox |
| 5 | The Matrix | - | - | - | $25,636,917 | 2,903 | $171,479,930 | 15% | Mar 31, 1999 | Warner Bros. |
| 6 | Never Been Kissed | - | - | - | $12,727,351 | 2,500 | $55,474,756 | 22.9% | Apr 9, 1999 | Twentieth Century Fox |
| 7 | A Midsummer Night's Dream | - | - | - | $12,641,004 | 1,099 | $16,071,990 | 78.7% | May 14, 1999 | Fox Searchlight Pictures |
| 8 | Life | - | - | - | $12,440,909 | 2,613 | $64,016,268 | 19.4% | Apr 16, 1999 | Universal Pictures |
| 9 | Election | - | - | - | $11,403,228 | 827 | $14,902,041 | 76.5% | Apr 23, 1999 | Paramount Pictures |
| 10 | Black Mask | - | - | - | $10,345,497 | 988 | $12,504,289 | 82.7% | May 14, 1999 | Artisan Entertainment |
| 11 | The Thirteenth Floor | - | - | - | $7,458,903 | 1,815 | $11,916,661 | 62.6% | May 28, 1999 | Sony Pictures Releasing |
| 12 | Trippin' | - | - | - | $7,418,848 | 781 | $9,017,070 | 82.3% | May 14, 1999 | October Films |
| 13 | The Love Letter | - | - | - | $6,234,097 | 817 | $8,302,478 | 75.1% | May 21, 1999 | DreamWorks Distribution |
| 14 | Tea with Mussolini | - | - | - | $6,229,203 | 284 | $14,401,563 | 43.3% | May 14, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 15 | Instinct | - | - | - | $6,186,990 | 2,129 | $34,105,207 | 18.1% | Jun 4, 1999 | Walt Disney Studios Motion Pictures |
| 16 | Analyze This | - | - | - | $5,019,172 | 2,537 | $106,885,658 | 4.7% | Mar 5, 1999 | Warner Bros. |
| 17 | 10 Things I Hate About You | - | - | - | $4,242,711 | 2,311 | $38,178,166 | 11.1% | Mar 31, 1999 | Walt Disney Studios Motion Pictures |
| 18 | Shakespeare in Love | - | - | - | $3,893,991 | 2,030 | $100,317,794 | 3.9% | Dec 11, 1998 | Miramax |
| 19 | Life Is Beautiful | - | - | - | $3,222,918 | 1,136 | $57,247,384 | 5.6% | Oct 23, 1998 | Miramax |
| 20 | Cookie's Fortune | - | - | - | $3,110,675 | 559 | $10,920,544 | 28.5% | Apr 2, 1999 | October Films |
| 21 | The Out-of-Towners | - | - | - | $2,350,718 | 2,128 | $28,544,120 | 8.2% | Apr 2, 1999 | Paramount Pictures |
| 22 | T-Rex: Back to the Cretaceous | - | - | - | $2,112,200 | 38 | $53,354,743 | 4% | Oct 23, 1998 | IMAX |
| 23 | Forces of Nature | - | - | - | $2,062,059 | 2,335 | $52,900,680 | 3.9% | Mar 19, 1999 | DreamWorks Distribution |
| 24 | She's All That | - | - | - | $1,864,081 | 2,654 | $63,366,989 | 2.9% | Jan 29, 1999 | Miramax |
| 25 | Pushing Tin | - | - | - | $1,820,846 | 1,284 | $8,408,835 | 21.7% | Apr 23, 1999 | Twentieth Century Fox |
| 26 | A Walk on the Moon | - | - | - | $1,646,291 | 246 | $4,750,660 | 34.7% | Mar 26, 1999 | Miramax |
| 27 | Mysteries of Egypt | - | - | - | $1,586,386 | 27 | $40,593,486 | 3.9% | Aug 21, 1998 | IMAX |
| 28 | Idle Hands | - | - | - | $1,546,791 | 1,611 | $4,152,230 | 37.3% | Apr 30, 1999 | Sony Pictures Releasing |
| 29 | Go | - | - | - | $1,510,951 | 1,563 | $16,943,454 | 8.9% | Apr 9, 1999 | Sony Pictures Releasing |
| 30 | October Sky | - | - | - | $1,470,797 | 1,702 | $32,570,685 | 4.5% | Feb 19, 1999 | Universal Pictures |
| 31 | Everest | - | - | - | $1,462,987 | 62 | $87,178,599 | 1.7% | Mar 6, 1998 | MacGillivray Freeman Films |
| 32 | Baby Geniuses | - | - | - | $1,238,510 | 1,702 | $27,250,736 | 4.5% | Mar 12, 1999 | Sony Pictures Releasing |
| 33 | Three Seasons | - | - | - | $1,186,320 | 66 | $2,021,698 | 58.7% | Apr 30, 1999 | October Films |
| 34 | The Winslow Boy | - | - | - | $1,141,577 | 141 | $3,957,934 | 28.8% | Apr 30, 1999 | Sony Pictures Classics |
| 35 | Lost & Found | - | - | - | $1,104,750 | 2,469 | $6,552,255 | 16.9% | Apr 23, 1999 | Warner Bros. |
| 36 | Austin Powers: The Spy Who Shagged Me | - | - | - | $1,082,175 | 3,314 | $206,040,086 | 0.5% | Jun 9, 1999 | New Line Cinema |
| 37 | Payback | - | - | - | $1,031,584 | 2,855 | $81,526,121 | 1.3% | Feb 5, 1999 | Paramount Pictures |
| 38 | Saving Private Ryan | - | - | - | $1,014,836 | 2,807 | $216,540,909 | 0.5% | Jul 24, 1998 | DreamWorks Distribution |
| 39 | Doug's 1st Movie | - | - | - | $942,385 | 2,268 | $19,440,089 | 4.8% | Mar 26, 1999 | Walt Disney Studios Motion Pictures |
| 40 | Africa's Elephant Kingdom | - | - | - | $895,416 | 15 | $13,485,455 | 6.6% | May 1, 1998 | IMAX |
| 41 | The King and I | - | - | - | $811,842 | 2,352 | $11,993,021 | 6.8% | Mar 19, 1999 | Warner Bros. |
| 42 | eXistenZ | - | - | - | $799,755 | 256 | $2,856,712 | 28% | Apr 23, 1999 | Miramax |
| 43 | The Other Sister | - | - | - | $779,731 | 1,863 | $27,807,627 | 2.8% | Feb 26, 1999 | Walt Disney Studios Motion Pictures |
| 44 | Encounter in the Third Dimension | - | - | - | $765,323 | 16 | $7,195,792 | 10.6% | Feb 26, 1999 | nWave Pictures |
| 45 | Foolish | - | - | - | $760,736 | 410 | $6,033,999 | 12.6% | Apr 9, 1999 | Artisan Entertainment |
| 46 | Twin Dragons | - | - | - | $731,249 | 1,131 | $8,359,717 | 8.7% | Apr 9, 1999 | Miramax |
| 47 | My Favorite Martian | - | - | - | $646,010 | 2,349 | $36,850,101 | 1.8% | Feb 12, 1999 | Walt Disney Studios Motion Pictures |
| 48 | Edtv | - | - | - | $637,720 | 2,631 | $22,431,897 | 2.8% | Mar 26, 1999 | Universal Pictures |
| 49 | Cruel Intentions | - | - | - | $620,225 | 2,312 | $38,328,567 | 1.6% | Mar 5, 1999 | Sony Pictures Releasing |
| 50 | The Dreamlife of Angels | - | - | - | $594,240 | 66 | $1,726,567 | 34.4% | Apr 2, 1999 | Sony Pictures Classics |
| 51 | The Deep End of the Ocean | - | - | - | $573,916 | 1,907 | $13,898,649 | 4.1% | Mar 12, 1999 | Sony Pictures Releasing |
| 52 | Thrill Ride: The Science of Fun | - | - | - | $537,607 | 81 | $18,798,590 | 2.9% | Jul 11, 1997 | Sony Pictures Classics |
| 53 | The Castle | - | - | - | $503,166 | 257 | $877,621 | 57.3% | May 7, 1999 | Miramax |
| 54 | Besieged | - | - | - | $476,271 | 153 | $2,048,740 | 23.2% | May 21, 1999 | Fine Line Features |
| 55 | Get Real | - | - | - | $456,039 | 40 | $1,152,979 | 39.6% | Apr 30, 1999 | Paramount Classics |
| 56 | Hideous Kinky | - | - | - | $450,335 | 78 | $1,263,279 | 35.6% | Apr 16, 1999 | Stratosphere Entertainment |
| 57 | Extreme | - | - | - | $444,036 | 21 | $12,475,172 | 3.6% | Apr 2, 1999 | IMAX |
| 58 | 8MM | - | - | - | $441,694 | 2,370 | $36,663,315 | 1.2% | Feb 26, 1999 | Sony Pictures Releasing |
| 59 | Lock, Stock and Two Smoking Barrels | - | - | - | $409,889 | 161 | $3,753,929 | 10.9% | Mar 5, 1999 | Gramercy Pictures (I) |
| 60 | The Rage: Carrie 2 | - | - | - | $372,547 | 2,286 | $17,762,705 | 2.1% | Mar 12, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 61 | Waking Ned Devine | - | - | - | $365,384 | 540 | $24,792,251 | 1.5% | Nov 20, 1998 | Fox Searchlight Pictures |
| 62 | The Prince of Egypt | - | - | - | $357,337 | 3,218 | $101,413,188 | 0.4% | Dec 18, 1998 | DreamWorks Distribution |
| 63 | Trekkies | - | - | - | $318,246 | 339 | $318,246 | 100% | May 21, 1999 | Paramount Classics |
| 64 | The Faculty | - | - | - | $316,664 | 2,365 | $40,283,321 | 0.8% | Dec 25, 1998 | Miramax |
| 65 | True Crime | - | - | - | $314,910 | 1,852 | $16,649,768 | 1.9% | Mar 19, 1999 | Warner Bros. |
| 66 | Lovers of the Arctic Circle | - | - | - | $306,725 | 23 | $317,422 | 96.6% | Apr 9, 1999 | Fine Line Features |
| 67 | This Is My Father | - | - | - | $302,650 | 51 | $1,083,975 | 27.9% | May 7, 1999 | Sony Pictures Classics |
| 68 | Island of the Sharks | - | - | - | $298,060 | 17 | $10,658,505 | 2.8% | Apr 23, 1999 | IMAX |
| 69 | Rushmore | - | - | - | $267,637 | 830 | $17,105,219 | 1.6% | Dec 11, 1998 | Walt Disney Studios Motion Pictures |
| 70 | Gods and Monsters | - | - | - | $220,244 | 149 | $6,451,628 | 3.4% | Nov 6, 1998 | Lionsgate |
| 71 | Patch Adams | - | - | - | $211,102 | 2,909 | $135,026,902 | 0.2% | Dec 25, 1998 | Universal Pictures |
| 72 | The Mod Squad | - | - | - | $209,894 | 2,290 | $13,263,993 | 1.6% | Mar 26, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 73 | Revelation | - | - | - | $206,755 | 15 | $206,755 | 100% | May 7, 1999 | Providence Entertainment |
| 74 | Open Your Eyes | - | - | - | $202,894 | 34 | $370,720 | 54.7% | Apr 16, 1999 | Artisan Entertainment |
| 75 | Asterix and Obelix vs. Caesar | - | - | - | $193,356 | 73 | $1,541,261 | 12.5% | Jun 4, 1999 | Lionsgate |
| 76 | The Swindle | - | - | - | $179,932 | 5 | $250,899 | 71.7% | Dec 23, 1998 | New Yorker Films |
| 77 | Blast from the Past | - | - | - | $160,634 | 2,544 | $26,511,114 | 0.6% | Feb 12, 1999 | New Line Cinema |
| 78 | Message in a Bottle | - | - | - | $146,836 | 2,545 | $52,880,016 | 0.3% | Feb 12, 1999 | Warner Bros. |
| 79 | Xiu Xiu: The Sent-Down Girl | - | - | - | $122,928 | 22 | $1,010,933 | 12.2% | May 7, 1999 | Stratosphere Entertainment |
| 80 | Eternity and a Day | - | - | - | $107,178 | 3 | $107,178 | 100% | May 28, 1999 | Artistic License |
| 81 | Edge of Seventeen | - | - | - | $105,099 | 10 | $871,759 | 12.1% | Apr 30, 1999 | Strand Releasing |
| 82 | Sarfarosh | - | - | - | $103,896 | 24 | $288,733 | 36% | Apr 30, 1999 | Eros Worldwide |
| 83 | Endurance | - | - | - | $98,503 | 20 | $137,124 | 71.8% | May 14, 1999 | Walt Disney Studios Motion Pictures |
| 84 | Goodbye Lover | - | - | - | $89,772 | 865 | $1,940,299 | 4.6% | Apr 16, 1999 | Warner Bros. |
| 85 | Limbo | - | - | - | $88,230 | 111 | $2,160,710 | 4.1% | Jun 4, 1999 | Sony Pictures Releasing |
| 86 | Buena Vista Social Club | - | - | - | $88,191 | 74 | $7,002,182 | 1.3% | Jun 4, 1999 | Artisan Entertainment |
| 87 | Dancemaker | - | - | - | $78,601 | 6 | $256,780 | 30.6% | Mar 3, 1999 | Artistic License |
| 88 | A Bug's Life | - | - | - | $77,453 | 2,773 | $162,798,565 | <0.1% | Nov 20, 1998 | Walt Disney Studios Motion Pictures |
| 89 | Central Station | - | - | - | $61,235 | 144 | $5,969,553 | 1% | Nov 20, 1998 | Sony Pictures Classics |
| 90 | Twice Upon a Yesterday | - | - | - | $53,516 | 47 | $279,757 | 19.1% | May 28, 1999 | Trimark Pictures |
| 91 | Southie | - | - | - | $52,819 | 2 | $52,819 | 100% | May 28, 1999 | Lionsgate |
| 92 | The Loss of Sexual Innocence | - | - | - | $50,354 | 26 | $164,022 | 30.7% | May 28, 1999 | Sony Pictures Releasing |
| 93 | The King of Masks | - | - | - | $29,937 | 23 | $1,113,103 | 2.7% | May 14, 1999 | The Samuel Goldwyn Company |
| 94 | Frogs for Snakes | - | - | - | $21,589 | 29 | $21,589 | 100% | May 21, 1999 | Artisan Entertainment |
| 95 | Stop Making Sense 1999 Re-release | - | - | - | $21,054 | 9 | $146,154 | 14.4% | May 28, 1999 | Palm Pictures |
| 96 | The Third Man | - | - | - | $13,576 | 5 | $618,173 | 2.2% | May 7, 1999 | Rialto Pictures |
| 97 | Goliathon | - | - | - | $12,368 | 14 | $17,368 | 71.2% | Apr 23, 1999 | Cowboy Pictures |
| 98 | After Life | - | - | - | $11,791 | 11 | $801,985 | 1.5% | May 14, 1999 | Artistic License |
| 99 | Desert Blue | - | - | - | $8,970 | 9 | $100,590 | 8.9% | Jun 4, 1999 | The Samuel Goldwyn Company |
| 100 | Free Enterprise | - | - | - | $7,905 | 9 | $30,229 | 26.2% | Jun 4, 1999 | Regent Releasing |
| 101 | Leila | - | - | - | $5,294 | 1 | $5,294 | 100% | May 14, 1999 | First Run |
| 102 | My Dinner with Andre | - | - | - | $5,073 | 1 | $5,073 | 100% | May 14, 1999 | WinStar Cinema |
| 103 | The Empty Mirror | - | - | - | $4,688 | 4 | $4,688 | 100% | May 7, 1999 | Lionsgate |
| 104 | Finding North | - | - | - | $3,954 | 3 | $27,466 | 14.4% | Jun 4, 1999 | Cowboy Pictures |
| 105 | Strawberry Fields | - | - | - | $3,347 | 2 | $3,347 | 100% | Jun 4, 1999 | Phaedra Cinema |
| 106 | I'm Crazy About Iris Blond | - | - | - | $3,303 | 1 | $3,303 | 100% | May 14, 1999 | Miramax |
| 107 | The Pusher | - | - | - | $1,656 | 1 | $1,656 | 100% | May 7, 1999 | First Run |
| 108 | The Underground Comedy Movie | - | - | - | $856 | 1 | $856 | 100% | May 14, 1999 | Phaedra Cinema |
| 109 | I Want You | - | - | - | $714 | 1 | $1,672 | 42.7% | Jun 4, 1999 | Gramercy Pictures (I) |
| 110 | Nobody | - | - | - | $488 | 1 | $488 | 100% | Jun 4, 1999 | Phaedra Cinema |
