| Rank
| Release
| Genre
| Budget
| Running Time
| Gross | Max Theaters | Total Gross | % of Total | Release Date | Distributor
|
|---|
| 1 | Wild Wild West | - | - | - | $103,991,771 | 3,342 | $113,804,681 | 91.4% | Jun 30, 1999 | Warner Bros. |
| 2 | Big Daddy | - | - | - | $96,497,120 | 3,254 | $163,479,795 | 59% | Jun 25, 1999 | Sony Pictures Releasing |
| 3 | The Blair Witch Project | - | - | - | $92,778,744 | 2,538 | $140,539,099 | 66% | Jul 16, 1999 | Artisan Entertainment |
| 4 | American Pie | - | - | - | $87,958,165 | 2,544 | $102,561,004 | 85.8% | Jul 9, 1999 | Universal Pictures |
| 5 | Runaway Bride | - | - | - | $84,184,355 | 3,240 | $152,257,509 | 55.3% | Jul 30, 1999 | Paramount Pictures |
| 6 | The Haunting | - | - | - | $80,331,453 | 2,881 | $91,411,151 | 87.9% | Jul 23, 1999 | DreamWorks Distribution |
| 7 | Tarzan | - | - | - | $71,988,880 | 3,131 | $171,091,819 | 42.1% | Jun 16, 1999 | Walt Disney Studios Motion Pictures |
| 8 | Inspector Gadget | - | - | - | $69,895,005 | 2,877 | $97,403,112 | 71.8% | Jul 23, 1999 | Walt Disney Studios Motion Pictures |
| 9 | Star Wars: Episode I - The Phantom Menace | - | - | - | $56,365,892 | 3,126 | $431,088,295 | 13.1% | May 19, 1999 | Twentieth Century Fox |
| 10 | Eyes Wide Shut | - | - | - | $52,899,408 | 2,483 | $55,691,208 | 95% | Jul 16, 1999 | Warner Bros. |
| 11 | Deep Blue Sea | - | - | - | $50,441,687 | 2,901 | $73,648,142 | 68.5% | Jul 30, 1999 | Warner Bros. |
| 12 | The General's Daughter | - | - | - | $47,209,800 | 2,858 | $102,705,852 | 46% | Jun 18, 1999 | Paramount Pictures |
| 13 | South Park: Bigger, Longer & Uncut | - | - | - | $45,890,343 | 2,128 | $52,037,603 | 88.2% | Jun 30, 1999 | Paramount Pictures |
| 14 | The Sixth Sense | - | - | - | $43,896,663 | 2,821 | $293,506,292 | 15% | Aug 6, 1999 | Walt Disney Studios Motion Pictures |
| 15 | Austin Powers: The Spy Who Shagged Me | - | - | - | $41,413,893 | 3,314 | $206,040,086 | 20.1% | Jun 9, 1999 | New Line Cinema |
| 16 | Lake Placid | - | - | - | $29,154,884 | 2,102 | $31,770,414 | 91.8% | Jul 16, 1999 | Twentieth Century Fox |
| 17 | Arlington Road | - | - | - | $23,496,662 | 1,631 | $24,756,177 | 94.9% | Jul 9, 1999 | Sony Pictures Releasing |
| 18 | The Wood | - | - | - | $23,157,009 | 1,191 | $25,059,640 | 92.4% | Jul 16, 1999 | Paramount Pictures |
| 19 | Notting Hill | - | - | - | $21,008,505 | 2,786 | $116,089,678 | 18.1% | May 28, 1999 | Universal Pictures |
| 20 | The Thomas Crown Affair | - | - | - | $20,896,461 | 2,427 | $69,305,181 | 30.2% | Aug 6, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 21 | Summer of Sam | - | - | - | $19,278,177 | 1,536 | $19,288,130 | 99.9% | Jul 2, 1999 | Walt Disney Studios Motion Pictures |
| 22 | Muppets from Space | - | - | - | $15,091,139 | 2,265 | $16,625,807 | 90.8% | Jul 14, 1999 | Sony Pictures Releasing |
| 23 | Mystery Men | - | - | - | $14,610,265 | 2,142 | $29,762,011 | 49.1% | Aug 6, 1999 | Universal Pictures |
| 24 | An Ideal Husband | - | - | - | $14,057,543 | 772 | $18,542,974 | 75.8% | Jun 18, 1999 | Miramax |
| 25 | Drop Dead Gorgeous | - | - | - | $9,779,877 | 1,207 | $10,571,408 | 92.5% | Jul 23, 1999 | New Line Cinema |
| 26 | The Iron Giant | - | - | - | $8,800,884 | 2,179 | $23,159,305 | 38% | Aug 3, 1999 | Warner Bros. |
| 27 | The Mummy | - | - | - | $7,200,135 | 3,411 | $155,516,138 | 4.6% | May 7, 1999 | Universal Pictures |
| 28 | Mysteries of Egypt | - | - | - | $4,777,387 | 27 | $40,593,486 | 11.8% | Aug 21, 1998 | IMAX |
| 29 | Dick | - | - | - | $4,735,324 | 1,522 | $6,262,878 | 75.6% | Aug 3, 1999 | Sony Pictures Releasing |
| 30 | The Matrix | - | - | - | $3,936,662 | 2,903 | $171,479,930 | 2.3% | Mar 31, 1999 | Warner Bros. |
| 31 | T-Rex: Back to the Cretaceous | - | - | - | $3,871,344 | 38 | $53,354,743 | 7.3% | Oct 23, 1998 | IMAX |
| 32 | The Red Violin | - | - | - | $3,833,148 | 261 | $10,019,109 | 38.3% | Nov 6, 1998 | Lionsgate |
| 33 | Entrapment | - | - | - | $3,328,638 | 2,879 | $87,704,396 | 3.8% | Apr 30, 1999 | Twentieth Century Fox |
| 34 | Elvis Gratton II: Miracle à Memphis | - | - | - | $3,316,272 | 91 | $3,316,272 | 100% | Jul 2, 1999 | Lionsgate |
| 35 | Run Lola Run | - | - | - | $3,271,682 | 172 | $7,267,585 | 45% | Jun 18, 1999 | Sony Pictures Classics |
| 36 | Tea with Mussolini | - | - | - | $3,265,465 | 284 | $14,401,563 | 22.7% | May 14, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 37 | Everest | - | - | - | $2,884,841 | 62 | $87,178,599 | 3.3% | Mar 6, 1998 | MacGillivray Freeman Films |
| 38 | Instinct | - | - | - | $2,701,632 | 2,129 | $34,105,207 | 7.9% | Jun 4, 1999 | Walt Disney Studios Motion Pictures |
| 39 | Shakespeare in Love | - | - | - | $2,280,902 | 2,030 | $100,317,794 | 2.3% | Dec 11, 1998 | Miramax |
| 40 | Buena Vista Social Club | - | - | - | $2,124,729 | 74 | $7,002,182 | 30.3% | Jun 4, 1999 | Artisan Entertainment |
| 41 | Extreme | - | - | - | $1,875,943 | 21 | $12,475,172 | 15% | Apr 2, 1999 | IMAX |
| 42 | Le Dîner de Cons | - | - | - | $1,831,329 | 67 | $4,071,548 | 45% | Jul 9, 1999 | Lionsgate |
| 43 | Never Been Kissed | - | - | - | $1,802,635 | 2,500 | $55,474,756 | 3.2% | Apr 9, 1999 | Twentieth Century Fox |
| 44 | 10 Things I Hate About You | - | - | - | $1,596,201 | 2,311 | $38,178,166 | 4.2% | Mar 31, 1999 | Walt Disney Studios Motion Pictures |
| 45 | Island of the Sharks | - | - | - | $1,493,971 | 17 | $10,658,505 | 14% | Apr 23, 1999 | IMAX |
| 46 | Life | - | - | - | $1,285,868 | 2,613 | $64,016,268 | 2% | Apr 16, 1999 | Universal Pictures |
| 47 | Encounter in the Third Dimension | - | - | - | $1,282,880 | 16 | $7,195,792 | 17.8% | Feb 26, 1999 | nWave Pictures |
| 48 | Africa's Elephant Kingdom | - | - | - | $1,241,446 | 15 | $13,485,455 | 9.2% | May 1, 1998 | IMAX |
| 49 | The Winslow Boy | - | - | - | $1,055,671 | 141 | $3,957,934 | 26.7% | Apr 30, 1999 | Sony Pictures Classics |
| 50 | Limbo | - | - | - | $980,093 | 111 | $2,160,710 | 45.4% | Jun 4, 1999 | Sony Pictures Releasing |
| 51 | The Thirteenth Floor | - | - | - | $810,029 | 1,815 | $11,916,661 | 6.8% | May 28, 1999 | Sony Pictures Releasing |
| 52 | After Life | - | - | - | $790,194 | 11 | $801,985 | 98.5% | May 14, 1999 | Artistic License |
| 53 | Analyze This | - | - | - | $773,529 | 2,537 | $106,885,658 | 0.7% | Mar 5, 1999 | Warner Bros. |
| 54 | Baby Geniuses | - | - | - | $705,323 | 1,702 | $27,250,736 | 2.6% | Mar 12, 1999 | Sony Pictures Releasing |
| 55 | Election | - | - | - | $678,597 | 827 | $14,902,041 | 4.6% | Apr 23, 1999 | Paramount Pictures |
| 56 | Trick | - | - | - | $638,432 | 94 | $2,087,228 | 30.6% | Jul 23, 1999 | Fine Line Features |
| 57 | Edge of Seventeen | - | - | - | $637,092 | 10 | $871,759 | 73.1% | Apr 30, 1999 | Strand Releasing |
| 58 | Thrill Ride: The Science of Fun | - | - | - | $633,428 | 81 | $18,798,590 | 3.4% | Jul 11, 1997 | Sony Pictures Classics |
| 59 | October Sky | - | - | - | $615,775 | 1,702 | $32,570,685 | 1.9% | Feb 19, 1999 | Universal Pictures |
| 60 | A Midsummer Night's Dream | - | - | - | $607,536 | 1,099 | $16,071,990 | 3.8% | May 14, 1999 | Fox Searchlight Pictures |
| 61 | Wolves | - | - | - | $603,140 | 16 | $4,811,282 | 12.5% | Jun 18, 1999 | IMAX |
| 62 | Wings of Courage | - | - | - | $561,183 | 11 | $15,054,636 | 3.7% | Apr 21, 1995 | Sony Pictures Classics |
| 63 | Autumn Tale | - | - | - | $541,808 | 53 | $2,205,339 | 24.6% | Jul 9, 1999 | October Films |
| 64 | Besieged | - | - | - | $517,795 | 153 | $2,048,740 | 25.3% | May 21, 1999 | Fine Line Features |
| 65 | Black Mask | - | - | - | $469,072 | 988 | $12,504,289 | 3.8% | May 14, 1999 | Artisan Entertainment |
| 66 | Straight from the Heart | - | - | - | $405,826 | 35 | $1,007,446 | 40.3% | Jun 18, 1999 | Video Sound |
| 67 | The Out-of-Towners | - | - | - | $405,581 | 2,128 | $28,544,120 | 1.4% | Apr 2, 1999 | Paramount Pictures |
| 68 | This Is My Father | - | - | - | $401,447 | 51 | $1,083,975 | 37% | May 7, 1999 | Sony Pictures Classics |
| 69 | Xiu Xiu: The Sent-Down Girl | - | - | - | $392,450 | 22 | $1,010,933 | 38.8% | May 7, 1999 | Stratosphere Entertainment |
| 70 | Go | - | - | - | $392,106 | 1,563 | $16,943,454 | 2.3% | Apr 9, 1999 | Sony Pictures Releasing |
| 71 | Genghis Blues | - | - | - | $374,550 | 6 | $374,550 | 100% | Jul 1, 1999 | Roxie Releasing |
| 72 | My Son the Fanatic | - | - | - | $348,168 | 20 | $417,683 | 83.4% | Jun 25, 1999 | Miramax |
| 73 | Cruel Intentions | - | - | - | $331,844 | 2,312 | $38,328,567 | 0.9% | Mar 5, 1999 | Sony Pictures Releasing |
| 74 | Cookie's Fortune | - | - | - | $317,448 | 559 | $10,920,544 | 2.9% | Apr 2, 1999 | October Films |
| 75 | Hindustan Ki Kasam | - | - | - | $310,330 | 22 | $310,330 | 100% | Jul 23, 1999 | Eros Worldwide |
| 76 | The Love Letter | - | - | - | $293,434 | 817 | $8,302,478 | 3.5% | May 21, 1999 | DreamWorks Distribution |
| 77 | Wildfire: Feel the Heat | - | - | - | $283,374 | 7 | $2,040,635 | 13.9% | Mar 12, 1999 | Primesco Communications Inc. |
| 78 | Get Real | - | - | - | $279,709 | 40 | $1,152,979 | 24.3% | Apr 30, 1999 | Paramount Classics |
| 79 | The King of Masks | - | - | - | $279,674 | 23 | $1,113,103 | 25.1% | May 14, 1999 | The Samuel Goldwyn Company |
| 80 | Asterix and Obelix vs. Caesar | - | - | - | $278,770 | 73 | $1,541,261 | 18.1% | Jun 4, 1999 | Lionsgate |
| 81 | My Life So Far | - | - | - | $272,665 | 22 | $635,620 | 42.9% | Jul 23, 1999 | Miramax |
| 82 | Doug's 1st Movie | - | - | - | $260,138 | 2,268 | $19,440,089 | 1.3% | Mar 26, 1999 | Walt Disney Studios Motion Pictures |
| 83 | Hote Hote Pyar Hogaya | - | - | - | $214,574 | 16 | $214,574 | 100% | Jul 2, 1999 | Eros Worldwide |
| 84 | My Favorite Martian | - | - | - | $189,909 | 2,349 | $36,850,101 | 0.5% | Feb 12, 1999 | Walt Disney Studios Motion Pictures |
| 85 | Three Seasons | - | - | - | $189,531 | 66 | $2,021,698 | 9.4% | Apr 30, 1999 | October Films |
| 86 | The Third Man | - | - | - | $168,395 | 5 | $618,173 | 27.2% | May 7, 1999 | Rialto Pictures |
| 87 | The Dreamlife of Angels | - | - | - | $149,919 | 66 | $1,726,567 | 8.7% | Apr 2, 1999 | Sony Pictures Classics |
| 88 | Foolish | - | - | - | $131,315 | 410 | $6,033,999 | 2.2% | Apr 9, 1999 | Artisan Entertainment |
| 89 | Twin Falls Idaho | - | - | - | $123,419 | 54 | $985,341 | 12.5% | Jul 30, 1999 | Sony Pictures Classics |
| 90 | The Castle | - | - | - | $121,359 | 257 | $877,621 | 13.8% | May 7, 1999 | Miramax |
| 91 | Twin Dragons | - | - | - | $119,392 | 1,131 | $8,359,717 | 1.4% | Apr 9, 1999 | Miramax |
| 92 | Trippin' | - | - | - | $106,386 | 781 | $9,017,070 | 1.2% | May 14, 1999 | October Films |
| 93 | Forces of Nature | - | - | - | $89,120 | 2,335 | $52,900,680 | 0.2% | Mar 19, 1999 | DreamWorks Distribution |
| 94 | Illuminata | - | - | - | $81,268 | 33 | $840,134 | 9.7% | Aug 3, 1999 | Artisan Entertainment |
| 95 | Late August, Early September | - | - | - | $69,400 | 1 | $69,400 | 100% | Jul 7, 1999 | Zeitgeist Films |
| 96 | Shiloh 2: Shiloh Season | - | - | - | $54,392 | 35 | $58,946 | 92.3% | Jun 25, 1999 | Legacy Releasing Corporation |
| 97 | Following | - | - | - | $38,107 | 2 | $48,482 | 78.6% | Apr 2, 1999 | Zeitgeist Films |
| 98 | A Walk on the Moon | - | - | - | $37,446 | 246 | $4,750,660 | 0.8% | Mar 26, 1999 | Miramax |
| 99 | Kohram | - | - | - | $31,727 | 11 | $70,257 | 45.2% | Aug 3, 1999 | Video Sound |
| 100 | Wildfire: Feel the Heat 1999 Re-release | - | - | - | $26,227 | 6 | $858,356 | 3.1% | Jun 18, 1999 | N/A |
| 101 | The Lovers on the Bridge | - | - | - | $22,653 | 2 | $29,679 | 76.3% | Jul 2, 1999 | Miramax |
| 102 | The Adventures of Sebastian Cole | - | - | - | $20,988 | 7 | $100,841 | 20.8% | Aug 6, 1999 | Paramount Classics |
| 103 | I'm Losing You | - | - | - | $13,996 | 2 | $13,996 | 100% | Jul 16, 1999 | Strand Releasing |
| 104 | Regret to Inform | - | - | - | $1,481 | 3 | $44,204 | 3.4% | Jun 25, 1999 | Artistic License |
