| Rank
| Release
| Genre
| Budget
| Running Time
| Gross | Max Theaters | Total Gross | % of Total | Release Date | Distributor
|
|---|
| 1 | The Bone Collector | - | - | - | $21,495,445 | 2,623 | $66,518,655 | 32.3% | Nov 5, 1999 | Universal Pictures |
| 2 | House on Haunted Hill | - | - | - | $13,744,340 | 2,710 | $40,846,082 | 33.6% | Oct 29, 1999 | Warner Bros. |
| 3 | Pokémon: The First Movie - Mewtwo Strikes Back | - | - | - | $10,096,848 | 3,043 | $85,744,662 | 11.8% | Nov 10, 1999 | Warner Bros. |
| 4 | The Bachelor | - | - | - | $8,589,354 | 2,524 | $21,760,240 | 39.5% | Nov 5, 1999 | New Line Cinema |
| 5 | The Insider | - | - | - | $8,153,445 | 1,844 | $29,089,912 | 28% | Nov 5, 1999 | Walt Disney Studios Motion Pictures |
| 6 | The Best Man | - | - | - | $6,857,125 | 1,348 | $34,102,780 | 20.1% | Oct 22, 1999 | Universal Pictures |
| 7 | Double Jeopardy | - | - | - | $6,841,915 | 3,002 | $116,741,558 | 5.9% | Sep 24, 1999 | Paramount Pictures |
| 8 | American Beauty | - | - | - | $5,728,676 | 1,990 | $130,096,601 | 4.4% | Sep 15, 1999 | DreamWorks Distribution |
| 9 | Fight Club | - | - | - | $5,025,176 | 1,966 | $37,030,102 | 13.6% | Oct 15, 1999 | Twentieth Century Fox |
| 10 | The Sixth Sense | - | - | - | $4,865,981 | 2,821 | $293,506,292 | 1.7% | Aug 6, 1999 | Walt Disney Studios Motion Pictures |
| 11 | Music of the Heart | - | - | - | $4,751,566 | 1,353 | $14,859,394 | 32% | Oct 29, 1999 | Miramax |
| 12 | Bringing Out the Dead | - | - | - | $3,659,224 | 1,967 | $16,797,191 | 21.8% | Oct 22, 1999 | Paramount Pictures |
| 13 | The Story of Us | - | - | - | $3,472,965 | 2,175 | $27,100,031 | 12.8% | Oct 15, 1999 | Universal Pictures |
| 14 | Three Kings | - | - | - | $2,923,656 | 2,942 | $60,652,036 | 4.8% | Oct 1, 1999 | Warner Bros. |
| 15 | Three to Tango | - | - | - | $2,143,521 | 2,234 | $10,570,375 | 20.3% | Oct 22, 1999 | Warner Bros. |
| 16 | Random Hearts | - | - | - | $1,832,386 | 2,697 | $31,502,583 | 5.8% | Oct 8, 1999 | Sony Pictures Releasing |
| 17 | Bats | - | - | - | $1,545,977 | 2,540 | $10,155,690 | 15.2% | Oct 22, 1999 | Destination Films |
| 18 | Being John Malkovich | - | - | - | $1,468,505 | 630 | $22,863,596 | 6.4% | Oct 29, 1999 | USA Films |
| 19 | Blue Streak | - | - | - | $1,413,306 | 2,735 | $68,518,533 | 2.1% | Sep 17, 1999 | Sony Pictures Releasing |
| 20 | Fifty | - | - | - | $1,045,096 | 31 | $3,328,240 | 31.4% | Oct 29, 1999 | IMAX |
| 21 | Superstar | - | - | - | $968,726 | 2,016 | $30,636,478 | 3.2% | Oct 8, 1999 | Paramount Pictures |
| 22 | The Adventures of Elmo in Grouchland | - | - | - | $918,764 | 1,210 | $11,683,047 | 7.9% | Oct 1, 1999 | Sony Pictures Releasing |
| 23 | The Omega Code | - | - | - | $779,353 | 450 | $12,614,346 | 6.2% | Oct 15, 1999 | Providence Entertainment |
| 24 | Mysteries of Egypt | - | - | - | $750,576 | 27 | $40,593,486 | 1.8% | Aug 21, 1998 | IMAX |
| 25 | Hum Saath-Saath Hain | - | - | - | $714,492 | 69 | $2,005,094 | 35.6% | Nov 5, 1999 | Eros Worldwide |
| 26 | Austin Powers: The Spy Who Shagged Me | - | - | - | $587,255 | 3,314 | $206,040,086 | 0.3% | Jun 9, 1999 | New Line Cinema |
| 27 | For Love of the Game | - | - | - | $492,090 | 2,933 | $35,188,640 | 1.4% | Sep 17, 1999 | Universal Pictures |
| 28 | Inspector Gadget | - | - | - | $416,752 | 2,877 | $97,403,112 | 0.4% | Jul 23, 1999 | Walt Disney Studios Motion Pictures |
| 29 | T-Rex: Back to the Cretaceous | - | - | - | $400,074 | 38 | $53,354,743 | 0.7% | Oct 23, 1998 | IMAX |
| 30 | Light It Up | - | - | - | $321,580 | 1,252 | $5,985,690 | 5.4% | Nov 10, 1999 | Twentieth Century Fox |
| 31 | The Thomas Crown Affair | - | - | - | $315,586 | 2,427 | $69,305,181 | 0.5% | Aug 6, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 32 | Mickey Blue Eyes | - | - | - | $302,632 | 2,573 | $33,864,342 | 0.9% | Aug 20, 1999 | Warner Bros. |
| 33 | Siegfried & Roy: The Magic Box | - | - | - | $282,876 | 22 | $5,231,283 | 5.4% | Oct 1, 1999 | IMAX |
| 34 | Happy, Texas | - | - | - | $281,230 | 146 | $1,955,933 | 14.4% | Oct 1, 1999 | Miramax |
| 35 | Run Lola Run | - | - | - | $268,163 | 172 | $7,267,585 | 3.7% | Jun 18, 1999 | Sony Pictures Classics |
| 36 | Deep Blue Sea | - | - | - | $256,282 | 2,901 | $73,648,142 | 0.3% | Jul 30, 1999 | Warner Bros. |
| 37 | The Straight Story | - | - | - | $252,395 | 186 | $6,203,044 | 4.1% | Oct 15, 1999 | Walt Disney Studios Motion Pictures |
| 38 | Everest | - | - | - | $248,076 | 62 | $87,178,599 | 0.3% | Mar 6, 1998 | MacGillivray Freeman Films |
| 39 | Romance | - | - | - | $241,560 | 74 | $1,585,642 | 15.2% | Sep 17, 1999 | Trimark Pictures |
| 40 | Bowfinger | - | - | - | $233,640 | 2,746 | $66,384,775 | 0.4% | Aug 13, 1999 | Universal Pictures |
| 41 | Mystery, Alaska | - | - | - | $215,196 | 1,704 | $8,891,623 | 2.4% | Oct 1, 1999 | Walt Disney Studios Motion Pictures |
| 42 | Island of the Sharks | - | - | - | $211,904 | 17 | $10,658,505 | 2% | Apr 23, 1999 | IMAX |
| 43 | Stir of Echoes | - | - | - | $211,282 | 1,943 | $21,142,914 | 1% | Sep 10, 1999 | Artisan Entertainment |
| 44 | Buena Vista Social Club | - | - | - | $211,266 | 74 | $7,002,182 | 3% | Jun 4, 1999 | Artisan Entertainment |
| 45 | Beefcake | - | - | - | $207,181 | 9 | $276,259 | 75% | Oct 15, 1999 | Strand Releasing |
| 46 | Runaway Bride | - | - | - | $201,798 | 3,240 | $152,257,509 | 0.1% | Jul 30, 1999 | Paramount Pictures |
| 47 | The 13th Warrior | - | - | - | $200,560 | 2,313 | $32,698,899 | 0.6% | Aug 27, 1999 | Walt Disney Studios Motion Pictures |
| 48 | The Limey | - | - | - | $153,888 | 105 | $3,204,663 | 4.8% | Oct 8, 1999 | Artisan Entertainment |
| 49 | The Iron Giant | - | - | - | $128,498 | 2,179 | $23,159,305 | 0.6% | Aug 3, 1999 | Warner Bros. |
| 50 | Stigmata | - | - | - | $126,012 | 2,901 | $50,046,268 | 0.3% | Sep 10, 1999 | Metro-Goldwyn-Mayer (MGM) |
| 51 | Lucie Aubrac | - | - | - | $120,844 | 19 | $394,079 | 30.7% | Sep 17, 1999 | USA Films |
| 52 | Boys Don't Cry | - | - | - | $116,180 | 365 | $11,540,607 | 1% | Oct 8, 1999 | Fox Searchlight Pictures |
| 53 | Tarzan | - | - | - | $111,396 | 3,131 | $171,091,819 | <0.1% | Jun 16, 1999 | Walt Disney Studios Motion Pictures |
| 54 | The Red Violin | - | - | - | $109,296 | 261 | $10,019,109 | 1.1% | Nov 6, 1998 | Lionsgate |
| 55 | Star Wars: Episode I - The Phantom Menace | - | - | - | $101,926 | 3,126 | $431,088,295 | <0.1% | May 19, 1999 | Twentieth Century Fox |
| 56 | The Haunting | - | - | - | $98,005 | 2,881 | $91,411,151 | 0.1% | Jul 23, 1999 | DreamWorks Distribution |
| 57 | Galapagos | - | - | - | $88,918 | 14 | $18,630,372 | 0.5% | Oct 29, 1999 | IMAX |
| 58 | Le Dîner de Cons | - | - | - | $74,386 | 67 | $4,071,548 | 1.8% | Jul 9, 1999 | Lionsgate |
| 59 | Drive Me Crazy | - | - | - | $60,906 | 2,233 | $17,845,337 | 0.3% | Oct 1, 1999 | Twentieth Century Fox |
| 60 | Body Shots | - | - | - | $52,158 | 309 | $752,122 | 6.9% | Oct 22, 1999 | New Line Cinema |
| 61 | Crazy in Alabama | - | - | - | $51,638 | 1,214 | $2,005,840 | 2.6% | Oct 22, 1999 | Sony Pictures Releasing |
| 62 | Thicker Than Water | - | - | - | $50,914 | 111 | $112,891 | 45.1% | Oct 29, 1999 | Palm Pictures |
| 63 | Princess Mononoke | - | - | - | $50,442 | 129 | $2,375,308 | 2.1% | Oct 29, 1999 | Miramax |
| 64 | Wolves | - | - | - | $38,204 | 16 | $4,811,282 | 0.8% | Jun 18, 1999 | IMAX |
| 65 | The Grandfather | - | - | - | $37,850 | 12 | $54,468 | 69.5% | Oct 8, 1999 | Miramax |
| 66 | All About My Mother | - | - | - | $34,328 | 145 | $8,272,296 | 0.4% | Nov 5, 1999 | Sony Pictures Classics |
| 67 | Africa's Elephant Kingdom | - | - | - | $31,608 | 15 | $13,485,455 | 0.2% | May 1, 1998 | IMAX |
| 68 | Train of Life | - | - | - | $27,876 | 45 | $98,687 | 28.2% | Nov 5, 1999 | Paramount Classics |
| 69 | The Children of the Marshland | - | - | - | $27,544 | 18 | $324,006 | 8.5% | Oct 1, 1999 | Lionsgate |
| 70 | Rosetta | - | - | - | $27,150 | 8 | $266,665 | 10.2% | Nov 5, 1999 | USA Films |
| 71 | American Movie | - | - | - | $26,364 | 29 | $1,165,795 | 2.3% | Nov 5, 1999 | Sony Pictures Classics |
| 72 | Man of the Century | - | - | - | $22,280 | 10 | $34,857 | 63.9% | Oct 29, 1999 | Fine Line Features |
| 73 | The Astronaut's Wife | - | - | - | $17,985 | 2,209 | $10,672,566 | 0.2% | Aug 27, 1999 | New Line Cinema |
| 74 | The Blair Witch Project | - | - | - | $8,985 | 2,538 | $140,539,099 | <0.1% | Jul 16, 1999 | Artisan Entertainment |
| 75 | Dreaming of Joseph Lees | - | - | - | $6,880 | 2 | $12,044 | 57.1% | Oct 29, 1999 | Fox Searchlight Pictures |
| 76 | The Suburbans | - | - | - | $181 | 11 | $11,130 | 1.6% | Oct 29, 1999 | Sony Pictures Releasing |
