| Rank
| Release
| Genre
| Budget
| Running Time
| Gross | Max Theaters | Total Gross | % of Total | Release Date | Distributor
|
|---|
| 1 | Toy Story 2 | - | - | - | $147,051,825 | 3,257 | $245,852,179 | 59.8% | Nov 19, 1999 | Walt Disney Studios Motion Pictures |
| 2 | The World Is Not Enough | - | - | - | $102,298,809 | 3,163 | $126,943,684 | 80.6% | Nov 19, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 3 | Sleepy Hollow | - | - | - | $83,763,540 | 3,069 | $101,071,502 | 82.9% | Nov 19, 1999 | Paramount Pictures |
| 4 | Double Jeopardy | - | - | - | $83,435,101 | 3,002 | $116,741,558 | 71.5% | Sep 24, 1999 | Paramount Pictures |
| 5 | Pokémon: The First Movie - Mewtwo Strikes Back | - | - | - | $82,590,382 | 3,043 | $85,744,662 | 96.3% | Nov 10, 1999 | Warner Bros. |
| 6 | The Bone Collector | - | - | - | $61,638,160 | 2,623 | $66,518,655 | 92.7% | Nov 5, 1999 | Universal Pictures |
| 7 | American Beauty | - | - | - | $58,564,190 | 1,990 | $130,096,601 | 45% | Sep 15, 1999 | DreamWorks Distribution |
| 8 | Three Kings | - | - | - | $58,178,524 | 2,942 | $60,652,036 | 95.9% | Oct 1, 1999 | Warner Bros. |
| 9 | End of Days | - | - | - | $55,498,865 | 2,652 | $66,889,043 | 83% | Nov 24, 1999 | Universal Pictures |
| 10 | The Sixth Sense | - | - | - | $47,162,317 | 2,821 | $293,506,292 | 16.1% | Aug 6, 1999 | Walt Disney Studios Motion Pictures |
| 11 | House on Haunted Hill | - | - | - | $39,641,406 | 2,710 | $40,846,082 | 97.1% | Oct 29, 1999 | Warner Bros. |
| 12 | Fight Club | - | - | - | $36,089,195 | 1,966 | $37,030,102 | 97.5% | Oct 15, 1999 | Twentieth Century Fox |
| 13 | The Best Man | - | - | - | $32,836,763 | 1,348 | $34,102,780 | 96.3% | Oct 22, 1999 | Universal Pictures |
| 14 | Random Hearts | - | - | - | $31,502,583 | 2,697 | $31,502,583 | 100% | Oct 8, 1999 | Sony Pictures Releasing |
| 15 | Superstar | - | - | - | $29,376,320 | 2,016 | $30,636,478 | 95.9% | Oct 8, 1999 | Paramount Pictures |
| 16 | Blue Streak | - | - | - | $27,638,088 | 2,735 | $68,518,533 | 40.3% | Sep 17, 1999 | Sony Pictures Releasing |
| 17 | The Green Mile | - | - | - | $27,411,122 | 2,875 | $136,801,374 | 20% | Dec 10, 1999 | Warner Bros. |
| 18 | Dogma | - | - | - | $27,152,665 | 1,292 | $30,652,890 | 88.6% | Nov 12, 1999 | Lionsgate |
| 19 | The Story of Us | - | - | - | $27,100,031 | 2,175 | $27,100,031 | 100% | Oct 15, 1999 | Universal Pictures |
| 20 | The Insider | - | - | - | $25,251,238 | 1,844 | $29,089,912 | 86.8% | Nov 5, 1999 | Walt Disney Studios Motion Pictures |
| 21 | The Bachelor | - | - | - | $21,103,690 | 2,524 | $21,760,240 | 97% | Nov 5, 1999 | New Line Cinema |
| 22 | Deuce Bigalow: Male Gigolo | - | - | - | $17,918,423 | 2,162 | $65,538,755 | 27.3% | Dec 10, 1999 | Walt Disney Studios Motion Pictures |
| 23 | Drive Me Crazy | - | - | - | $17,845,337 | 2,233 | $17,845,337 | 100% | Oct 1, 1999 | Twentieth Century Fox |
| 24 | Anywhere But Here | - | - | - | $17,785,518 | 1,686 | $18,670,401 | 95.3% | Nov 12, 1999 | Twentieth Century Fox |
| 25 | Bringing Out the Dead | - | - | - | $16,448,280 | 1,967 | $16,797,191 | 97.9% | Oct 22, 1999 | Paramount Pictures |
| 26 | Being John Malkovich | - | - | - | $15,918,620 | 630 | $22,863,596 | 69.6% | Oct 29, 1999 | USA Films |
| 27 | Music of the Heart | - | - | - | $14,542,833 | 1,353 | $14,859,394 | 97.9% | Oct 29, 1999 | Miramax |
| 28 | The Messenger: The Story of Joan of Arc | - | - | - | $14,088,797 | 2,147 | $14,276,317 | 98.7% | Nov 12, 1999 | Sony Pictures Releasing |
| 29 | The Omega Code | - | - | - | $12,224,625 | 450 | $12,614,346 | 96.9% | Oct 15, 1999 | Providence Entertainment |
| 30 | The Adventures of Elmo in Grouchland | - | - | - | $11,683,047 | 1,210 | $11,683,047 | 100% | Oct 1, 1999 | Sony Pictures Releasing |
| 31 | Three to Tango | - | - | - | $10,570,375 | 2,234 | $10,570,375 | 100% | Oct 22, 1999 | Warner Bros. |
| 32 | For Love of the Game | - | - | - | $10,328,975 | 2,933 | $35,188,640 | 29.4% | Sep 17, 1999 | Universal Pictures |
| 33 | Bats | - | - | - | $10,155,690 | 2,540 | $10,155,690 | 100% | Oct 22, 1999 | Destination Films |
| 34 | Mystery, Alaska | - | - | - | $8,891,623 | 1,704 | $8,891,623 | 100% | Oct 1, 1999 | Walt Disney Studios Motion Pictures |
| 35 | Stigmata | - | - | - | $8,106,506 | 2,901 | $50,046,268 | 16.2% | Sep 10, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 36 | Light It Up | - | - | - | $5,679,511 | 1,252 | $5,985,690 | 94.9% | Nov 10, 1999 | Twentieth Century Fox |
| 37 | Mysteries of Egypt | - | - | - | $5,543,343 | 27 | $40,593,486 | 13.7% | Aug 21, 1998 | IMAX |
| 38 | Runaway Bride | - | - | - | $4,801,686 | 3,240 | $152,257,509 | 3.2% | Jul 30, 1999 | Paramount Pictures |
| 39 | Stir of Echoes | - | - | - | $4,581,588 | 1,943 | $21,142,914 | 21.7% | Sep 10, 1999 | Artisan Entertainment |
| 40 | Star Wars: Episode I - The Phantom Menace | - | - | - | $4,339,575 | 3,126 | $431,088,295 | 1% | May 19, 1999 | Twentieth Century Fox |
| 41 | Flawless | - | - | - | $4,178,114 | 483 | $4,488,529 | 93.1% | Nov 26, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 42 | Stuart Little | - | - | - | $3,688,000 | 3,151 | $140,035,367 | 2.6% | Dec 17, 1999 | Sony Pictures Releasing |
| 43 | The Straight Story | - | - | - | $3,669,616 | 186 | $6,203,044 | 59.2% | Oct 15, 1999 | Walt Disney Studios Motion Pictures |
| 44 | Inspector Gadget | - | - | - | $3,373,758 | 2,877 | $97,403,112 | 3.5% | Jul 23, 1999 | Walt Disney Studios Motion Pictures |
| 45 | Fifty | - | - | - | $3,328,240 | 31 | $3,328,240 | 100% | Oct 29, 1999 | IMAX |
| 46 | T-Rex: Back to the Cretaceous | - | - | - | $3,047,438 | 38 | $53,354,743 | 5.7% | Oct 23, 1998 | IMAX |
| 47 | The Thomas Crown Affair | - | - | - | $2,941,702 | 2,427 | $69,305,181 | 4.2% | Aug 6, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 48 | The Limey | - | - | - | $2,872,653 | 105 | $3,204,663 | 89.6% | Oct 8, 1999 | Artisan Entertainment |
| 49 | Boys Don't Cry | - | - | - | $2,308,764 | 365 | $11,540,607 | 20% | Oct 8, 1999 | Fox Searchlight Pictures |
| 50 | Bicentennial Man | - | - | - | $2,237,000 | 2,767 | $58,223,861 | 3.8% | Dec 17, 1999 | Walt Disney Studios Motion Pictures |
| 51 | Jakob the Liar | - | - | - | $2,224,592 | 1,200 | $4,956,401 | 44.9% | Sep 24, 1999 | Sony Pictures Releasing |
| 52 | Princess Mononoke | - | - | - | $2,201,409 | 129 | $2,375,308 | 92.7% | Oct 29, 1999 | Miramax |
| 53 | Mumford | - | - | - | $2,054,123 | 1,452 | $4,555,459 | 45.1% | Sep 24, 1999 | Walt Disney Studios Motion Pictures |
| 54 | Crazy in Alabama | - | - | - | $2,005,840 | 1,214 | $2,005,840 | 100% | Oct 22, 1999 | Sony Pictures Releasing |
| 55 | Happy, Texas | - | - | - | $1,955,933 | 146 | $1,955,933 | 100% | Oct 1, 1999 | Miramax |
| 56 | Everest | - | - | - | $1,951,956 | 62 | $87,178,599 | 2.2% | Mar 6, 1998 | MacGillivray Freeman Films |
| 57 | Hum Saath-Saath Hain | - | - | - | $1,936,004 | 69 | $2,005,094 | 96.6% | Nov 5, 1999 | Eros Worldwide |
| 58 | The Blair Witch Project | - | - | - | $1,926,102 | 2,538 | $140,539,099 | 1.4% | Jul 16, 1999 | Artisan Entertainment |
| 59 | Bowfinger | - | - | - | $1,819,355 | 2,746 | $66,384,775 | 2.7% | Aug 13, 1999 | Universal Pictures |
| 60 | Siegfried & Roy: The Magic Box | - | - | - | $1,713,518 | 22 | $5,231,283 | 32.8% | Oct 1, 1999 | IMAX |
| 61 | The Haunting | - | - | - | $1,647,391 | 2,881 | $91,411,151 | 1.8% | Jul 23, 1999 | DreamWorks Distribution |
| 62 | Anna and the King | - | - | - | $1,551,000 | 2,132 | $39,263,420 | 4% | Dec 17, 1999 | Twentieth Century Fox |
| 63 | Buena Vista Social Club | - | - | - | $1,539,479 | 74 | $7,002,182 | 22% | Jun 4, 1999 | Artisan Entertainment |
| 64 | Deep Blue Sea | - | - | - | $1,525,305 | 2,901 | $73,648,142 | 2.1% | Jul 30, 1999 | Warner Bros. |
| 65 | The 13th Warrior | - | - | - | $1,484,205 | 2,313 | $32,698,899 | 4.5% | Aug 27, 1999 | Walt Disney Studios Motion Pictures |
| 66 | Romance | - | - | - | $1,446,580 | 74 | $1,585,642 | 91.2% | Sep 17, 1999 | Trimark Pictures |
| 67 | Run Lola Run | - | - | - | $1,416,766 | 172 | $7,267,585 | 19.5% | Jun 18, 1999 | Sony Pictures Classics |
| 68 | Island of the Sharks | - | - | - | $1,400,611 | 17 | $10,658,505 | 13.1% | Apr 23, 1999 | IMAX |
| 69 | American Pie | - | - | - | $1,370,889 | 2,544 | $102,561,004 | 1.3% | Jul 9, 1999 | Universal Pictures |
| 70 | Mansfield Park | - | - | - | $1,191,677 | 152 | $4,775,847 | 25% | Nov 19, 1999 | Miramax |
| 71 | Extreme | - | - | - | $1,116,812 | 21 | $12,475,172 | 9% | Apr 2, 1999 | IMAX |
| 72 | The Iron Giant | - | - | - | $1,090,683 | 2,179 | $23,159,305 | 4.7% | Aug 3, 1999 | Warner Bros. |
| 73 | Tarzan | - | - | - | $1,021,226 | 3,131 | $171,091,819 | 0.6% | Jun 16, 1999 | Walt Disney Studios Motion Pictures |
| 74 | All About My Mother | - | - | - | $1,018,249 | 145 | $8,272,296 | 12.3% | Nov 5, 1999 | Sony Pictures Classics |
| 75 | Any Given Sunday | - | - | - | $1,006,549 | 2,505 | $75,530,832 | 1.3% | Dec 22, 1999 | Warner Bros. |
| 76 | Liberty Heights | - | - | - | $868,604 | 115 | $3,736,868 | 23.2% | Nov 19, 1999 | Warner Bros. |
| 77 | Mickey Blue Eyes | - | - | - | $867,809 | 2,573 | $33,864,342 | 2.6% | Aug 20, 1999 | Warner Bros. |
| 78 | Body Shots | - | - | - | $752,122 | 309 | $752,122 | 100% | Oct 22, 1999 | New Line Cinema |
| 79 | Man on the Moon | - | - | - | $679,802 | 2,079 | $34,607,430 | 2% | Dec 22, 1999 | Universal Pictures |
| 80 | Felicia's Journey | - | - | - | $642,178 | 49 | $824,295 | 77.9% | Nov 12, 1999 | Artisan Entertainment |
| 81 | Austin Powers: The Spy Who Shagged Me | - | - | - | $640,664 | 3,314 | $206,040,086 | 0.3% | Jun 9, 1999 | New Line Cinema |
| 82 | Big Daddy | - | - | - | $636,986 | 3,254 | $163,479,795 | 0.4% | Jun 25, 1999 | Sony Pictures Releasing |
| 83 | Grey Owl | - | - | - | $632,617 | 70 | $632,617 | 100% | Oct 1, 1999 | Miramax |
| 84 | Le Dîner de Cons | - | - | - | $618,106 | 67 | $4,071,548 | 15.2% | Jul 9, 1999 | Lionsgate |
| 85 | In Too Deep | - | - | - | $615,510 | 674 | $14,011,454 | 4.4% | Aug 27, 1999 | Miramax |
| 86 | Guinevere | - | - | - | $547,430 | 310 | $632,283 | 86.6% | Sep 24, 1999 | Miramax |
| 87 | Africa's Elephant Kingdom | - | - | - | $546,795 | 15 | $13,485,455 | 4.1% | May 1, 1998 | IMAX |
| 88 | Galapagos | - | - | - | $545,245 | 14 | $18,630,372 | 2.9% | Oct 29, 1999 | IMAX |
| 89 | Wolves | - | - | - | $523,329 | 16 | $4,811,282 | 10.9% | Jun 18, 1999 | IMAX |
| 90 | The End of the Affair | - | - | - | $486,979 | 688 | $10,827,816 | 4.5% | Dec 3, 1999 | Sony Pictures Releasing |
| 91 | Plunkett & Macleane | - | - | - | $474,900 | 475 | $474,900 | 100% | Oct 1, 1999 | USA Films |
| 92 | The Red Violin | - | - | - | $469,669 | 261 | $10,019,109 | 4.7% | Nov 6, 1998 | Lionsgate |
| 93 | Dudley Do-Right | - | - | - | $421,000 | 1,855 | $9,974,410 | 4.2% | Aug 27, 1999 | Universal Pictures |
| 94 | Dillagi | - | - | - | $401,245 | 38 | $401,245 | 100% | Nov 19, 1999 | Eros Worldwide |
| 95 | Laura Cadieux... la suite | - | - | - | $345,841 | 59 | $777,477 | 44.5% | Dec 3, 1999 | Alliance Atlantis Vivafilm |
| 96 | American Movie | - | - | - | $339,864 | 29 | $1,165,795 | 29.2% | Nov 5, 1999 | Sony Pictures Classics |
| 97 | Lucie Aubrac | - | - | - | $326,903 | 19 | $394,079 | 83% | Sep 17, 1999 | USA Films |
| 98 | The Children of the Marshland | - | - | - | $324,006 | 18 | $324,006 | 100% | Oct 1, 1999 | Lionsgate |
| 99 | Autumn Tale | - | - | - | $313,315 | 53 | $2,205,339 | 14.2% | Jul 9, 1999 | October Films |
| 100 | Sweet and Lowdown | - | - | - | $308,473 | 239 | $4,197,015 | 7.3% | Dec 3, 1999 | Sony Pictures Classics |
| 101 | The General's Daughter | - | - | - | $279,824 | 2,858 | $102,705,852 | 0.3% | Jun 18, 1999 | Paramount Pictures |
| 102 | Beefcake | - | - | - | $276,259 | 9 | $276,259 | 100% | Oct 15, 1999 | Strand Releasing |
| 103 | The Wood | - | - | - | $276,242 | 1,191 | $25,059,640 | 1.1% | Jul 16, 1999 | Paramount Pictures |
| 104 | The Astronaut's Wife | - | - | - | $269,888 | 2,209 | $10,672,566 | 2.5% | Aug 27, 1999 | New Line Cinema |
| 105 | Thrill Ride: The Science of Fun | - | - | - | $268,903 | 81 | $18,798,590 | 1.4% | Jul 11, 1997 | Sony Pictures Classics |
| 106 | Rosetta | - | - | - | $266,665 | 8 | $266,665 | 100% | Nov 5, 1999 | USA Films |
| 107 | Tea with Mussolini | - | - | - | $261,284 | 284 | $14,401,563 | 1.8% | May 14, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 108 | Better Than Chocolate | - | - | - | $261,116 | 130 | $2,015,406 | 13% | Aug 13, 1999 | Trimark Pictures |
| 109 | Chill Factor | - | - | - | $238,922 | 2,558 | $11,263,966 | 2.1% | Sep 3, 1999 | Warner Bros. |
| 110 | Mystery Men | - | - | - | $232,441 | 2,142 | $29,762,011 | 0.8% | Aug 6, 1999 | Universal Pictures |
| 111 | Ride with the Devil | - | - | - | $232,372 | 60 | $635,096 | 36.6% | Nov 26, 1999 | USA Films |
| 112 | The Cider House Rules | - | - | - | $231,013 | 1,738 | $57,545,092 | 0.4% | Dec 10, 1999 | Miramax |
| 113 | Earth | - | - | - | $217,201 | 18 | $424,798 | 51.1% | Sep 10, 1999 | Zeitgeist Films |
| 114 | The Minus Man | - | - | - | $206,483 | 45 | $370,668 | 55.7% | Sep 10, 1999 | Artisan Entertainment |
| 115 | Cradle Will Rock | - | - | - | $179,925 | 506 | $2,903,404 | 6.2% | Dec 10, 1999 | Walt Disney Studios Motion Pictures |
| 116 | Show Me Love | - | - | - | $169,331 | 7 | $169,331 | 100% | Oct 15, 1999 | Strand Releasing |
| 117 | The Legend of 1900 | - | - | - | $167,435 | 58 | $167,435 | 100% | Oct 29, 1999 | Fine Line Features |
| 118 | Lake Placid | - | - | - | $165,909 | 2,102 | $31,770,414 | 0.5% | Jul 16, 1999 | Twentieth Century Fox |
| 119 | Notting Hill | - | - | - | $165,483 | 2,786 | $116,089,678 | 0.1% | May 28, 1999 | Universal Pictures |
| 120 | Mast | - | - | - | $158,928 | 25 | $158,928 | 100% | Oct 15, 1999 | Eros Worldwide |
| 121 | Encounter in the Third Dimension | - | - | - | $151,462 | 16 | $7,195,792 | 2.1% | Feb 26, 1999 | nWave Pictures |
| 122 | Wild Wild West | - | - | - | $150,572 | 3,342 | $113,804,681 | 0.1% | Jun 30, 1999 | Warner Bros. |
| 123 | Matroni and Me | - | - | - | $130,572 | 40 | $130,572 | 100% | Oct 8, 1999 | Alliance Atlantis Vivafilm |
| 124 | Breakfast of Champions | - | - | - | $118,275 | 11 | $178,278 | 66.3% | Sep 17, 1999 | Walt Disney Studios Motion Pictures |
| 125 | Sugar Town | - | - | - | $116,699 | 22 | $178,095 | 65.5% | Sep 17, 1999 | USA Films |
| 126 | Tumbleweeds | - | - | - | $113,730 | 307 | $1,350,248 | 8.4% | Nov 26, 1999 | Fine Line Features |
| 127 | Thicker Than Water | - | - | - | $112,891 | 111 | $112,891 | 100% | Oct 29, 1999 | Palm Pictures |
| 128 | Outside Providence | - | - | - | $104,749 | 1,052 | $7,302,522 | 1.4% | Sep 1, 1999 | Miramax |
| 129 | Eyes Wide Shut | - | - | - | $100,442 | 2,483 | $55,691,208 | 0.2% | Jul 16, 1999 | Warner Bros. |
| 130 | Train of Life | - | - | - | $98,687 | 45 | $98,687 | 100% | Nov 5, 1999 | Paramount Classics |
| 131 | The IMAX Nutcracker | - | - | - | $91,283 | 26 | $1,009,291 | 9% | Nov 12, 1999 | IMAX |
| 132 | Vaastav: The Reality | - | - | - | $81,367 | 16 | $81,367 | 100% | Oct 15, 1999 | Eros Worldwide |
| 133 | Virtual Sexuality | - | - | - | $74,007 | 101 | $74,007 | 100% | Dec 3, 1999 | Sony Pictures Releasing |
| 134 | Bedrooms and Hallways | - | - | - | $73,782 | 7 | $136,049 | 54.2% | Sep 3, 1999 | First Run |
| 135 | Dil Kya Kare | - | - | - | $54,603 | 35 | $284,856 | 19.2% | Sep 24, 1999 | Eros Worldwide |
| 136 | The Grandfather | - | - | - | $54,468 | 12 | $54,468 | 100% | Oct 8, 1999 | Miramax |
| 137 | Simon Sez | - | - | - | $48,216 | 504 | $292,152 | 16.5% | Sep 24, 1999 | Independent Artists |
| 138 | Magnolia | - | - | - | $43,641 | 1,086 | $22,455,976 | 0.2% | Dec 17, 1999 | New Line Cinema |
| 139 | Man of the Century | - | - | - | $34,857 | 10 | $34,857 | 100% | Oct 29, 1999 | Fine Line Features |
| 140 | Holy Smoke | - | - | - | $33,307 | 93 | $1,765,545 | 1.9% | Dec 3, 1999 | Miramax |
| 141 | Beyond the Clouds | - | - | - | $31,738 | 4 | $31,738 | 100% | Dec 1, 1999 | Sceneries Distribution |
| 142 | 42 Up | - | - | - | $22,675 | 5 | $300,880 | 7.5% | Nov 17, 1999 | First Run |
| 143 | New Rose Hotel | - | - | - | $21,521 | 2 | $21,521 | 100% | Oct 1, 1999 | Lionsgate |
| 144 | The War Zone | - | - | - | $18,335 | 12 | $254,441 | 7.2% | Dec 10, 1999 | Lot 47 Films |
| 145 | Finding North | - | - | - | $18,235 | 3 | $27,466 | 66.4% | Jun 4, 1999 | Cowboy Pictures |
| 146 | Molly | - | - | - | $17,650 | 12 | $17,650 | 100% | Oct 22, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 147 | Beyond the Mat | - | - | - | $17,186 | 298 | $2,053,648 | 0.8% | Oct 22, 1999 | Lionsgate |
| 148 | 2by4 | - | - | - | $17,162 | 1 | $17,162 | 100% | Nov 26, 1999 | Strand Releasing |
| 149 | A Map of the World | - | - | - | $16,698 | 19 | $544,965 | 3.1% | Dec 3, 1999 | First Look International |
| 150 | Diamonds | - | - | - | $12,895 | 27 | $88,428 | 14.6% | Dec 10, 1999 | Miramax |
| 151 | Girl, Interrupted | - | - | - | $12,547 | 1,935 | $28,912,646 | <0.1% | Dec 21, 1999 | Sony Pictures Releasing |
| 152 | On the Ropes | - | - | - | $12,531 | 5 | $46,737 | 26.8% | Aug 18, 1999 | Wellspring Media |
| 153 | Dreaming of Joseph Lees | - | - | - | $12,044 | 2 | $12,044 | 100% | Oct 29, 1999 | Fox Searchlight Pictures |
| 154 | Joe the King | - | - | - | $11,793 | 18 | $60,279 | 19.6% | Oct 15, 1999 | Trimark Pictures |
| 155 | Hell's Kitchen | - | - | - | $11,710 | 2 | $11,710 | 100% | Dec 3, 1999 | Cowboy Pictures |
| 156 | The Suburbans | - | - | - | $11,130 | 11 | $11,130 | 100% | Oct 29, 1999 | Sony Pictures Releasing |
| 157 | Agnes Browne | - | - | - | $10,473 | 21 | $148,853 | 7% | Dec 3, 1999 | USA Films |
| 158 | Topsy-Turvy | - | - | - | $9,819 | 224 | $6,208,548 | 0.2% | Dec 15, 1999 | USA Films |
| 159 | The Emperor and the Assassin | - | - | - | $9,080 | 37 | $1,267,239 | 0.7% | Dec 15, 1999 | Sony Pictures Classics |
| 160 | Fever Pitch | - | - | - | $3,736 | 1 | $3,736 | 100% | Oct 15, 1999 | Phaedra Cinema |
| 161 | Snow Falling on Cedars | - | - | - | $2,720 | 1,155 | $14,417,593 | <0.1% | Dec 22, 1999 | Universal Pictures |
| 162 | Onegin | - | - | - | $2,646 | 6 | $206,128 | 1.3% | Dec 17, 1999 | The Samuel Goldwyn Company |
| 163 | Suits | - | - | - | $676 | 2 | $3,676 | 18.4% | Sep 24, 1999 | Taurus Entertainment Company |
