| Rank
| Release
| Genre
| Budget
| Running Time
| Gross | Max Theaters | Total Gross | % of Total | Release Date | Distributor
|
|---|
| 1 | Star Wars: Episode I - The Phantom Menace | - | - | - | $48,659,066 | 3,126 | $431,088,295 | 11.3% | May 19, 1999 | 20th Century Fox |
| 2 | Notting Hill | - | - | - | $21,729,710 | 2,786 | $116,089,678 | 18.7% | May 28, 1999 | Universal Pictures |
| 3 | The Mummy | - | - | - | $10,287,820 | 3,411 | $155,516,138 | 6.6% | May 7, 1999 | Universal Pictures |
| 4 | Instinct | - | - | - | $6,186,990 | 2,129 | $34,105,207 | 18.1% | Jun 4, 1999 | Walt Disney Studios Motion Pictures |
| 5 | Entrapment | - | - | - | $6,143,460 | 2,879 | $87,704,396 | 7% | Apr 30, 1999 | 20th Century Fox |
| 6 | The Matrix | - | - | - | $3,496,169 | 2,903 | $171,479,930 | 2% | Mar 31, 1999 | Warner Bros. |
| 7 | The Thirteenth Floor | - | - | - | $3,180,451 | 1,815 | $11,916,661 | 26.7% | May 28, 1999 | Sony Pictures Releasing |
| 8 | Never Been Kissed | - | - | - | $1,845,870 | 2,500 | $55,474,756 | 3.3% | Apr 9, 1999 | 20th Century Fox |
| 9 | A Midsummer Night's Dream | - | - | - | $1,834,332 | 1,099 | $16,071,990 | 11.4% | May 14, 1999 | Fox Searchlight Pictures |
| 10 | Black Mask | - | - | - | $1,327,437 | 988 | $12,504,289 | 10.6% | May 14, 1999 | Artisan Entertainment |
| 11 | Election | - | - | - | $1,253,694 | 827 | $14,902,041 | 8.4% | Apr 23, 1999 | Paramount Pictures |
| 12 | Life | - | - | - | $1,253,670 | 2,613 | $64,016,268 | 2% | Apr 16, 1999 | Universal Pictures |
| 13 | Mysteries of Egypt | - | - | - | $1,216,783 | 27 | $40,593,486 | 3% | Aug 21, 1998 | IMAX |
| 14 | Tea with Mussolini | - | - | - | $1,163,085 | 284 | $14,401,563 | 8.1% | May 14, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 15 | The Love Letter | - | - | - | $1,122,192 | 817 | $8,302,478 | 13.5% | May 21, 1999 | DreamWorks Distribution |
| 16 | Austin Powers: The Spy Who Shagged Me | - | - | - | $1,082,175 | 3,314 | $206,040,086 | 0.5% | Jun 9, 1999 | New Line Cinema |
| 17 | Trippin' | - | - | - | $968,421 | 781 | $9,017,070 | 10.7% | May 14, 1999 | October Films |
| 18 | Analyze This | - | - | - | $477,363 | 2,537 | $106,885,658 | 0.4% | Mar 5, 1999 | Warner Bros. |
| 19 | 10 Things I Hate About You | - | - | - | $470,418 | 2,311 | $38,178,166 | 1.2% | Mar 31, 1999 | Walt Disney Studios Motion Pictures |
| 20 | Shakespeare in Love | - | - | - | $459,297 | 2,030 | $100,317,794 | 0.5% | Dec 11, 1998 | Miramax |
| 21 | Everest | - | - | - | $456,292 | 62 | $87,178,599 | 0.5% | Mar 6, 1998 | MacGillivray Freeman Films |
| 22 | T-Rex: Back to the Cretaceous | - | - | - | $441,810 | 38 | $53,354,743 | 0.8% | Oct 23, 1998 | IMAX |
| 23 | The Winslow Boy | - | - | - | $380,298 | 141 | $3,957,934 | 9.6% | Apr 30, 1999 | Sony Pictures Classics |
| 24 | Extreme | - | - | - | $378,203 | 21 | $12,475,172 | 3% | Apr 2, 1999 | IMAX |
| 25 | Life Is Beautiful | - | - | - | $345,240 | 1,136 | $57,247,384 | 0.6% | Oct 23, 1998 | Miramax |
| 26 | Cookie's Fortune | - | - | - | $328,170 | 559 | $10,920,544 | 3% | Apr 2, 1999 | October Films |
| 27 | Baby Geniuses | - | - | - | $304,287 | 1,702 | $27,250,736 | 1.1% | Mar 12, 1999 | Sony Pictures Releasing |
| 28 | My Favorite Martian | - | - | - | $250,302 | 2,349 | $36,850,101 | 0.7% | Feb 12, 1999 | Walt Disney Studios Motion Pictures |
| 29 | Payback | - | - | - | $244,788 | 2,855 | $81,526,121 | 0.3% | Feb 5, 1999 | Paramount Pictures |
| 30 | Three Seasons | - | - | - | $233,133 | 66 | $2,021,698 | 11.5% | Apr 30, 1999 | October Films |
| 31 | October Sky | - | - | - | $211,080 | 1,702 | $32,570,685 | 0.6% | Feb 19, 1999 | Universal Pictures |
| 32 | Asterix and Obelix vs. Caesar | - | - | - | $193,356 | 73 | $1,541,261 | 12.5% | Jun 4, 1999 | Lionsgate |
| 33 | Forces of Nature | - | - | - | $183,579 | 2,335 | $52,900,680 | 0.3% | Mar 19, 1999 | DreamWorks Distribution |
| 34 | A Walk on the Moon | - | - | - | $183,096 | 246 | $4,750,660 | 3.9% | Mar 26, 1999 | Miramax |
| 35 | Open Your Eyes | - | - | - | $160,053 | 34 | $370,720 | 43.2% | Apr 16, 1999 | Artisan Entertainment |
| 36 | Africa's Elephant Kingdom | - | - | - | $153,435 | 15 | $13,485,455 | 1.1% | May 1, 1998 | IMAX |
| 37 | Encounter in the Third Dimension | - | - | - | $148,794 | 16 | $7,195,792 | 2.1% | Feb 26, 1999 | nWave Pictures |
| 38 | Besieged | - | - | - | $148,389 | 153 | $2,048,740 | 7.2% | May 21, 1999 | Fine Line Features |
| 39 | She's All That | - | - | - | $147,057 | 2,654 | $63,366,989 | 0.2% | Jan 29, 1999 | Miramax |
| 40 | The Out-of-Towners | - | - | - | $145,512 | 2,128 | $28,544,120 | 0.5% | Apr 2, 1999 | Paramount Pictures |
| 41 | The Other Sister | - | - | - | $144,810 | 1,863 | $27,807,627 | 0.5% | Feb 26, 1999 | Walt Disney Studios Motion Pictures |
| 42 | The Rage: Carrie 2 | - | - | - | $123,191 | 2,286 | $17,762,705 | 0.7% | Mar 12, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 43 | Cruel Intentions | - | - | - | $120,369 | 2,312 | $38,328,567 | 0.3% | Mar 5, 1999 | Sony Pictures Releasing |
| 44 | The Dreamlife of Angels | - | - | - | $100,860 | 66 | $1,726,567 | 5.8% | Apr 2, 1999 | Sony Pictures Classics |
| 45 | The Castle | - | - | - | $99,105 | 257 | $877,621 | 11.3% | May 7, 1999 | Miramax |
| 46 | Doug's 1st Movie | - | - | - | $95,889 | 2,268 | $19,440,089 | 0.5% | Mar 26, 1999 | Walt Disney Studios Motion Pictures |
| 47 | Get Real | - | - | - | $90,219 | 40 | $1,152,979 | 7.8% | Apr 30, 1999 | Paramount Classics |
| 48 | Limbo | - | - | - | $88,230 | 111 | $2,160,710 | 4.1% | Jun 4, 1999 | Sony Pictures Releasing |
| 49 | Buena Vista Social Club | - | - | - | $88,191 | 74 | $7,002,182 | 1.3% | Jun 4, 1999 | Artisan Entertainment |
| 50 | Hideous Kinky | - | - | - | $83,052 | 78 | $1,263,279 | 6.6% | Apr 16, 1999 | Stratosphere Entertainment |
| 51 | Island of the Sharks | - | - | - | $82,611 | 17 | $10,658,505 | 0.8% | Apr 23, 1999 | IMAX |
| 52 | Foolish | - | - | - | $80,607 | 410 | $6,033,999 | 1.3% | Apr 9, 1999 | Artisan Entertainment |
| 53 | This Is My Father | - | - | - | $80,493 | 51 | $1,083,975 | 7.4% | May 7, 1999 | Sony Pictures Classics |
| 54 | Eternity and a Day | - | - | - | $76,474 | 3 | $107,178 | 71.4% | May 28, 1999 | Artistic License |
| 55 | Lost & Found | - | - | - | $75,387 | 2,469 | $6,552,255 | 1.2% | Apr 23, 1999 | Warner Bros. |
| 56 | Go | - | - | - | $74,355 | 1,563 | $16,943,454 | 0.4% | Apr 9, 1999 | Sony Pictures Releasing |
| 57 | Rushmore | - | - | - | $70,260 | 830 | $17,105,219 | 0.4% | Dec 11, 1998 | Walt Disney Studios Motion Pictures |
| 58 | Idle Hands | - | - | - | $61,404 | 1,611 | $4,152,230 | 1.5% | Apr 30, 1999 | Sony Pictures Releasing |
| 59 | Waking Ned Devine | - | - | - | $57,641 | 540 | $24,792,251 | 0.2% | Nov 20, 1998 | Fox Searchlight Pictures |
| 60 | Trekkies | - | - | - | $56,987 | 339 | $318,246 | 17.9% | May 21, 1999 | Paramount Classics |
| 61 | Thrill Ride: The Science of Fun | - | - | - | $56,607 | 81 | $18,798,590 | 0.3% | Jul 11, 1997 | Sony Pictures Classics |
| 62 | Pushing Tin | - | - | - | $51,453 | 1,284 | $8,408,835 | 0.6% | Apr 23, 1999 | 20th Century Fox |
| 63 | Endurance | - | - | - | $44,356 | 20 | $137,124 | 32.3% | May 14, 1999 | Walt Disney Studios Motion Pictures |
| 64 | Twice Upon a Yesterday | - | - | - | $40,107 | 47 | $279,757 | 14.3% | May 28, 1999 | Trimark Pictures |
| 65 | Edtv | - | - | - | $38,742 | 2,631 | $22,431,897 | 0.2% | Mar 26, 1999 | Universal Pictures |
| 66 | The King and I | - | - | - | $36,483 | 2,352 | $11,993,021 | 0.3% | Mar 19, 1999 | Warner Bros. |
| 67 | Southie | - | - | - | $31,047 | 2 | $52,819 | 58.8% | May 28, 1999 | Lionsgate |
| 68 | Patch Adams | - | - | - | $11,934 | 2,909 | $135,026,902 | <0.1% | Dec 25, 1998 | Universal Pictures |
| 69 | Desert Blue | - | - | - | $8,970 | 9 | $100,590 | 8.9% | Jun 4, 1999 | The Samuel Goldwyn Company |
| 70 | Free Enterprise | - | - | - | $7,905 | 9 | $30,229 | 26.2% | Jun 4, 1999 | Regent Releasing |
| 71 | Finding North | - | - | - | $3,954 | 3 | $27,466 | 14.4% | Jun 4, 1999 | Cowboy Pictures |
| 72 | Strawberry Fields | - | - | - | $3,347 | 2 | $3,347 | 100% | Jun 4, 1999 | Phaedra Cinema |
| 73 | I Want You | - | - | - | $714 | 1 | $1,672 | 42.7% | Jun 4, 1999 | Gramercy Pictures (I) |
| 74 | Nobody | - | - | - | $488 | 1 | $488 | 100% | Jun 4, 1999 | Phaedra Cinema |
