Top Grossing Drama Movies in October 1999
| Rank | Title | Language | Domestic | Worldwide |
|---|---|---|---|---|
| 1 | The Kid | $69,691,949 | $110,317,580 | |
| 2 | Three Kings |  EN | $60,652,036 | $107,752,036 |
| 3 | Fight Club |  IN | $37,030,102 | $101,321,009 |
| 4 | Random Hearts | EN | $31,502,583 | $74,608,570 |
| 5 | The Story of Us | EN | $27,100,031 | $58,900,031 |
| 6 | The Best Man | EN | $34,102,780 | $34,573,780 |
| 7 | Being John Malkovich | EN | $22,863,596 | $23,106,795 |
| 8 | Drive Me Crazy | EN | $17,845,337 | $22,593,409 |
| 9 | The Legend of 1900 | EN | $167,435 | $21,061,339 |
| 10 | Bringing Out the Dead | EN | $16,797,191 | $16,798,496 |
| 11 | Music of the Heart | EN | $14,859,394 | $14,936,407 |
| 12 | The Omega Code | EN | $12,614,346 | $12,614,346 |
| 13 | Boys Don't Cry | EN | $11,540,607 | $11,540,607 |
| 14 | Mystery, Alaska | EN | $8,891,623 | $8,891,623 |
| 15 | The Road Home |  CN | $1,280,490 | $6,780,490 |
| 16 | The Straight Story | EN | $6,203,044 | $6,454,772 |
| 17 | The Limey | EN | $3,204,663 | $3,325,736 |
| 18 | Beyond the Clouds | EN | $2,053,648 | $2,053,648 |
| 19 | Crazy in Alabama | EN | $2,005,840 | $2,005,840 |
| 20 | Body Shots | EN | $752,122 | $752,122 |
| 21 | Gloomy Sunday |  DE | $585,604 | $646,532 |
| 22 | Grey Owl | EN | $632,617 | $632,617 |
| 23 | Plunkett & Macleane | EN | $474,900 | $474,900 |
| 24 | Audition |  JP | $131,296 | $365,049 |
| 25 | Beefcake | EN | $276,259 | $276,259 |
| 26 | Show Me Love |  SE | $169,331 | $219,331 |
| 27 | Thicker Than Water | EN | $112,891 | $112,891 |
| 28 | Julien Donkey-Boy | EN | $85,400 | $92,442 |
| 29 | Peppermint Candy |  KR | - | $89,184 |
| 30 | Joe the King | EN | $60,279 | $60,279 |
| 31 | The Grandfather |  ES | $54,468 | $54,838 |
| 32 | Whiteboyz | EN | $38,738 | $38,738 |
| 33 | Across a Gold Prairie | JP | - | $38,403 |
| 34 | Captain Pantoja and the Special Services | ES | - | $38,380 |
| 35 | New Rose Hotel | EN | $21,521 | $21,521 |
| 36 | Molly | EN | $17,650 | $17,650 |
| 37 | Soft Fruit | EN | $13,654 | $13,654 |
| 38 | Dreaming of Joseph Lees | EN | $12,044 | $12,044 |
| 39 | The Suburbans | EN | $11,130 | $11,130 |
| 40 | All My Loved Ones |  CS | $6,237 | $6,237 |
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