| Rank
| Release
| Genre
| Budget
| Running Time
| Gross | Max Theaters | Total Gross | % of Total | Release Date | Distributor
|
|---|
| 1 | Double Jeopardy | - | - | - | $68,429,062 | 3,002 | $116,741,558 | 58.6% | Sep 24, 1999 | Paramount Pictures |
| 2 | Three Kings | - | - | - | $53,943,917 | 2,942 | $60,652,036 | 88.9% | Oct 1, 1999 | Warner Bros. |
| 3 | American Beauty | - | - | - | $44,186,588 | 1,990 | $130,096,601 | 34% | Sep 15, 1999 | DreamWorks Distribution |
| 4 | The Sixth Sense | - | - | - | $32,523,066 | 2,821 | $293,506,292 | 11.1% | Aug 6, 1999 | Walt Disney Studios Motion Pictures |
| 5 | Random Hearts | - | - | - | $29,449,025 | 2,697 | $31,502,583 | 93.5% | Oct 8, 1999 | Sony Pictures Releasing |
| 6 | Fight Club | - | - | - | $28,067,833 | 1,966 | $37,030,102 | 75.8% | Oct 15, 1999 | Twentieth Century Fox |
| 7 | Blue Streak | - | - | - | $24,882,713 | 2,735 | $68,518,533 | 36.3% | Sep 17, 1999 | Sony Pictures Releasing |
| 8 | Superstar | - | - | - | $23,681,381 | 2,016 | $30,636,478 | 77.3% | Oct 8, 1999 | Paramount Pictures |
| 9 | The Story of Us | - | - | - | $22,507,995 | 2,175 | $27,100,031 | 83.1% | Oct 15, 1999 | Universal Pictures |
| 10 | The Best Man | - | - | - | $18,369,565 | 1,348 | $34,102,780 | 53.9% | Oct 22, 1999 | Universal Pictures |
| 11 | House on Haunted Hill | - | - | - | $17,166,574 | 2,710 | $40,846,082 | 42% | Oct 29, 1999 | Warner Bros. |
| 12 | Drive Me Crazy | - | - | - | $16,443,674 | 2,233 | $17,845,337 | 92.1% | Oct 1, 1999 | Twentieth Century Fox |
| 13 | Bringing Out the Dead | - | - | - | $11,811,454 | 1,967 | $16,797,191 | 70.3% | Oct 22, 1999 | Paramount Pictures |
| 14 | The Adventures of Elmo in Grouchland | - | - | - | $10,075,980 | 1,210 | $11,683,047 | 86.2% | Oct 1, 1999 | Sony Pictures Releasing |
| 15 | For Love of the Game | - | - | - | $9,465,208 | 2,933 | $35,188,640 | 26.9% | Sep 17, 1999 | Universal Pictures |
| 16 | Mystery, Alaska | - | - | - | $8,328,147 | 1,704 | $8,891,623 | 93.7% | Oct 1, 1999 | Walt Disney Studios Motion Pictures |
| 17 | Bats | - | - | - | $7,975,195 | 2,540 | $10,155,690 | 78.5% | Oct 22, 1999 | Destination Films |
| 18 | Three to Tango | - | - | - | $7,874,358 | 2,234 | $10,570,375 | 74.5% | Oct 22, 1999 | Warner Bros. |
| 19 | Stigmata | - | - | - | $7,001,802 | 2,901 | $50,046,268 | 14% | Sep 10, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 20 | The Omega Code | - | - | - | $5,510,515 | 450 | $12,614,346 | 43.7% | Oct 15, 1999 | Providence Entertainment |
| 21 | Music of the Heart | - | - | - | $3,993,474 | 1,353 | $14,859,394 | 26.9% | Oct 29, 1999 | Miramax |
| 22 | Stir of Echoes | - | - | - | $3,802,982 | 1,943 | $21,142,914 | 18% | Sep 10, 1999 | Artisan Entertainment |
| 23 | Runaway Bride | - | - | - | $3,003,920 | 3,240 | $152,257,509 | 2% | Jul 30, 1999 | Paramount Pictures |
| 24 | Star Wars: Episode I - The Phantom Menace | - | - | - | $2,967,095 | 3,126 | $431,088,295 | 0.7% | May 19, 1999 | Twentieth Century Fox |
| 25 | Mysteries of Egypt | - | - | - | $2,427,491 | 27 | $40,593,486 | 6% | Aug 21, 1998 | IMAX |
| 26 | Jakob the Liar | - | - | - | $2,224,592 | 1,200 | $4,956,401 | 44.9% | Sep 24, 1999 | Sony Pictures Releasing |
| 27 | Inspector Gadget | - | - | - | $2,174,306 | 2,877 | $97,403,112 | 2.2% | Jul 23, 1999 | Walt Disney Studios Motion Pictures |
| 28 | The Thomas Crown Affair | - | - | - | $2,164,688 | 2,427 | $69,305,181 | 3.1% | Aug 6, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 29 | Mumford | - | - | - | $1,873,513 | 1,452 | $4,555,459 | 41.1% | Sep 24, 1999 | Walt Disney Studios Motion Pictures |
| 30 | The Blair Witch Project | - | - | - | $1,837,300 | 2,538 | $140,539,099 | 1.3% | Jul 16, 1999 | Artisan Entertainment |
| 31 | Crazy in Alabama | - | - | - | $1,662,013 | 1,214 | $2,005,840 | 82.9% | Oct 22, 1999 | Sony Pictures Releasing |
| 32 | The Haunting | - | - | - | $1,550,652 | 2,881 | $91,411,151 | 1.7% | Jul 23, 1999 | DreamWorks Distribution |
| 33 | T-Rex: Back to the Cretaceous | - | - | - | $1,424,918 | 38 | $53,354,743 | 2.7% | Oct 23, 1998 | IMAX |
| 34 | American Pie | - | - | - | $1,370,889 | 2,544 | $102,561,004 | 1.3% | Jul 9, 1999 | Universal Pictures |
| 35 | Happy, Texas | - | - | - | $1,262,737 | 146 | $1,955,933 | 64.6% | Oct 1, 1999 | Miramax |
| 36 | Bowfinger | - | - | - | $1,214,000 | 2,746 | $66,384,775 | 1.8% | Aug 13, 1999 | Universal Pictures |
| 37 | Romance | - | - | - | $1,169,943 | 74 | $1,585,642 | 73.8% | Sep 17, 1999 | Trimark Pictures |
| 38 | The 13th Warrior | - | - | - | $1,162,005 | 2,313 | $32,698,899 | 3.6% | Aug 27, 1999 | Walt Disney Studios Motion Pictures |
| 39 | The Limey | - | - | - | $1,155,075 | 105 | $3,204,663 | 36% | Oct 8, 1999 | Artisan Entertainment |
| 40 | Run Lola Run | - | - | - | $1,073,910 | 172 | $7,267,585 | 14.8% | Jun 18, 1999 | Sony Pictures Classics |
| 41 | Deep Blue Sea | - | - | - | $1,002,251 | 2,901 | $73,648,142 | 1.4% | Jul 30, 1999 | Warner Bros. |
| 42 | Buena Vista Social Club | - | - | - | $954,085 | 74 | $7,002,182 | 13.6% | Jun 4, 1999 | Artisan Entertainment |
| 43 | Everest | - | - | - | $948,479 | 62 | $87,178,599 | 1.1% | Mar 6, 1998 | MacGillivray Freeman Films |
| 44 | Tarzan | - | - | - | $856,027 | 3,131 | $171,091,819 | 0.5% | Jun 16, 1999 | Walt Disney Studios Motion Pictures |
| 45 | The Iron Giant | - | - | - | $833,402 | 2,179 | $23,159,305 | 3.6% | Aug 3, 1999 | Warner Bros. |
| 46 | Boys Don't Cry | - | - | - | $744,078 | 365 | $11,540,607 | 6.4% | Oct 8, 1999 | Fox Searchlight Pictures |
| 47 | Body Shots | - | - | - | $672,035 | 309 | $752,122 | 89.4% | Oct 22, 1999 | New Line Cinema |
| 48 | Grey Owl | - | - | - | $632,617 | 70 | $632,617 | 100% | Oct 1, 1999 | Miramax |
| 49 | In Too Deep | - | - | - | $615,510 | 674 | $14,011,454 | 4.4% | Aug 27, 1999 | Miramax |
| 50 | Big Daddy | - | - | - | $606,170 | 3,254 | $163,479,795 | 0.4% | Jun 25, 1999 | Sony Pictures Releasing |
| 51 | Siegfried & Roy: The Magic Box | - | - | - | $604,658 | 22 | $5,231,283 | 11.6% | Oct 1, 1999 | IMAX |
| 52 | Island of the Sharks | - | - | - | $585,362 | 17 | $10,658,505 | 5.5% | Apr 23, 1999 | IMAX |
| 53 | Extreme | - | - | - | $539,280 | 21 | $12,475,172 | 4.3% | Apr 2, 1999 | IMAX |
| 54 | The Straight Story | - | - | - | $521,715 | 186 | $6,203,044 | 8.4% | Oct 15, 1999 | Walt Disney Studios Motion Pictures |
| 55 | Guinevere | - | - | - | $507,649 | 310 | $632,283 | 80.3% | Sep 24, 1999 | Miramax |
| 56 | Africa's Elephant Kingdom | - | - | - | $486,303 | 15 | $13,485,455 | 3.6% | May 1, 1998 | IMAX |
| 57 | Plunkett & Macleane | - | - | - | $474,900 | 475 | $474,900 | 100% | Oct 1, 1999 | USA Films |
| 58 | Wolves | - | - | - | $456,664 | 16 | $4,811,282 | 9.5% | Jun 18, 1999 | IMAX |
| 59 | Dudley Do-Right | - | - | - | $421,000 | 1,855 | $9,974,410 | 4.2% | Aug 27, 1999 | Universal Pictures |
| 60 | Mickey Blue Eyes | - | - | - | $415,112 | 2,573 | $33,864,342 | 1.2% | Aug 20, 1999 | Warner Bros. |
| 61 | The Red Violin | - | - | - | $318,473 | 261 | $10,019,109 | 3.2% | Nov 6, 1998 | Lionsgate |
| 62 | Autumn Tale | - | - | - | $313,315 | 53 | $2,205,339 | 14.2% | Jul 9, 1999 | October Films |
| 63 | Le Dîner de Cons | - | - | - | $307,682 | 67 | $4,071,548 | 7.6% | Jul 9, 1999 | Lionsgate |
| 64 | Being John Malkovich | - | - | - | $281,571 | 630 | $22,863,596 | 1.2% | Oct 29, 1999 | USA Films |
| 65 | The General's Daughter | - | - | - | $279,824 | 2,858 | $102,705,852 | 0.3% | Jun 18, 1999 | Paramount Pictures |
| 66 | The Wood | - | - | - | $276,242 | 1,191 | $25,059,640 | 1.1% | Jul 16, 1999 | Paramount Pictures |
| 67 | The Children of the Marshland | - | - | - | $272,445 | 18 | $324,006 | 84.1% | Oct 1, 1999 | Lionsgate |
| 68 | Thrill Ride: The Science of Fun | - | - | - | $268,903 | 81 | $18,798,590 | 1.4% | Jul 11, 1997 | Sony Pictures Classics |
| 69 | Tea with Mussolini | - | - | - | $261,284 | 284 | $14,401,563 | 1.8% | May 14, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 70 | Better Than Chocolate | - | - | - | $261,116 | 130 | $2,015,406 | 13% | Aug 13, 1999 | Trimark Pictures |
| 71 | Chill Factor | - | - | - | $238,922 | 2,558 | $11,263,966 | 2.1% | Sep 3, 1999 | Warner Bros. |
| 72 | Fifty | - | - | - | $234,340 | 31 | $3,328,240 | 7% | Oct 29, 1999 | IMAX |
| 73 | Mystery Men | - | - | - | $232,441 | 2,142 | $29,762,011 | 0.8% | Aug 6, 1999 | Universal Pictures |
| 74 | Earth | - | - | - | $217,201 | 18 | $424,798 | 51.1% | Sep 10, 1999 | Zeitgeist Films |
| 75 | The Minus Man | - | - | - | $206,483 | 45 | $370,668 | 55.7% | Sep 10, 1999 | Artisan Entertainment |
| 76 | The Astronaut's Wife | - | - | - | $173,934 | 2,209 | $10,672,566 | 1.6% | Aug 27, 1999 | New Line Cinema |
| 77 | Lucie Aubrac | - | - | - | $173,400 | 19 | $394,079 | 44% | Sep 17, 1999 | USA Films |
| 78 | Show Me Love | - | - | - | $169,331 | 7 | $169,331 | 100% | Oct 15, 1999 | Strand Releasing |
| 79 | Lake Placid | - | - | - | $165,909 | 2,102 | $31,770,414 | 0.5% | Jul 16, 1999 | Twentieth Century Fox |
| 80 | Notting Hill | - | - | - | $165,483 | 2,786 | $116,089,678 | 0.1% | May 28, 1999 | Universal Pictures |
| 81 | Mast | - | - | - | $158,928 | 25 | $158,928 | 100% | Oct 15, 1999 | Eros Worldwide |
| 82 | Encounter in the Third Dimension | - | - | - | $151,462 | 16 | $7,195,792 | 2.1% | Feb 26, 1999 | nWave Pictures |
| 83 | Wild Wild West | - | - | - | $150,572 | 3,342 | $113,804,681 | 0.1% | Jun 30, 1999 | Warner Bros. |
| 84 | Matroni and Me | - | - | - | $130,572 | 40 | $130,572 | 100% | Oct 8, 1999 | Alliance Atlantis Vivafilm |
| 85 | Princess Mononoke | - | - | - | $119,212 | 129 | $2,375,308 | 5% | Oct 29, 1999 | Miramax |
| 86 | Breakfast of Champions | - | - | - | $118,275 | 11 | $178,278 | 66.3% | Sep 17, 1999 | Walt Disney Studios Motion Pictures |
| 87 | Sugar Town | - | - | - | $116,699 | 22 | $178,095 | 65.5% | Sep 17, 1999 | USA Films |
| 88 | Outside Providence | - | - | - | $104,749 | 1,052 | $7,302,522 | 1.4% | Sep 1, 1999 | Miramax |
| 89 | Eyes Wide Shut | - | - | - | $100,442 | 2,483 | $55,691,208 | 0.2% | Jul 16, 1999 | Warner Bros. |
| 90 | Vaastav: The Reality | - | - | - | $81,367 | 16 | $81,367 | 100% | Oct 15, 1999 | Eros Worldwide |
| 91 | Bedrooms and Hallways | - | - | - | $73,782 | 7 | $136,049 | 54.2% | Sep 3, 1999 | First Run |
| 92 | Beefcake | - | - | - | $69,078 | 9 | $276,259 | 25% | Oct 15, 1999 | Strand Releasing |
| 93 | Dil Kya Kare | - | - | - | $54,603 | 35 | $284,856 | 19.2% | Sep 24, 1999 | Eros Worldwide |
| 94 | Thicker Than Water | - | - | - | $50,914 | 111 | $112,891 | 45.1% | Oct 29, 1999 | Palm Pictures |
| 95 | Simon Sez | - | - | - | $48,216 | 504 | $292,152 | 16.5% | Sep 24, 1999 | Independent Artists |
| 96 | The Legend of 1900 | - | - | - | $39,200 | 58 | $167,435 | 23.4% | Oct 29, 1999 | Fine Line Features |
| 97 | All About My Mother | - | - | - | $34,328 | 145 | $8,272,296 | 0.4% | Nov 5, 1999 | Sony Pictures Classics |
| 98 | Galapagos | - | - | - | $32,428 | 14 | $18,630,372 | 0.2% | Oct 29, 1999 | IMAX |
| 99 | New Rose Hotel | - | - | - | $21,521 | 2 | $21,521 | 100% | Oct 1, 1999 | Lionsgate |
| 100 | Finding North | - | - | - | $18,235 | 3 | $27,466 | 66.4% | Jun 4, 1999 | Cowboy Pictures |
| 101 | Molly | - | - | - | $17,650 | 12 | $17,650 | 100% | Oct 22, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 102 | Beyond the Mat | - | - | - | $17,186 | 298 | $2,053,648 | 0.8% | Oct 22, 1999 | Lionsgate |
| 103 | The Grandfather | - | - | - | $16,618 | 12 | $54,468 | 30.5% | Oct 8, 1999 | Miramax |
| 104 | On the Ropes | - | - | - | $12,531 | 5 | $46,737 | 26.8% | Aug 18, 1999 | Wellspring Media |
| 105 | Joe the King | - | - | - | $11,793 | 18 | $60,279 | 19.6% | Oct 15, 1999 | Trimark Pictures |
| 106 | Man of the Century | - | - | - | $7,184 | 10 | $34,857 | 20.6% | Oct 29, 1999 | Fine Line Features |
| 107 | Dreaming of Joseph Lees | - | - | - | $6,880 | 2 | $12,044 | 57.1% | Oct 29, 1999 | Fox Searchlight Pictures |
| 108 | The Suburbans | - | - | - | $6,256 | 11 | $11,130 | 56.2% | Oct 29, 1999 | Sony Pictures Releasing |
| 109 | Fever Pitch | - | - | - | $3,736 | 1 | $3,736 | 100% | Oct 15, 1999 | Phaedra Cinema |
| 110 | Suits | - | - | - | $676 | 2 | $3,676 | 18.4% | Sep 24, 1999 | Taurus Entertainment Company |
