Top Grossing Comedy Movies in October 1999
| Rank | Title | Language | Domestic | Worldwide |
|---|---|---|---|---|
| 1 | Three Kings |  EN | $60,652,036 | $107,752,036 |
| 2 | The Story of Us | EN | $27,100,031 | $58,900,031 |
| 3 | The Best Man | EN | $34,102,780 | $34,573,780 |
| 4 | Superstar | EN | $30,636,478 | $30,636,478 |
| 5 | Being John Malkovich | EN | $22,863,596 | $23,106,795 |
| 6 | Drive Me Crazy | EN | $17,845,337 | $22,593,409 |
| 7 | The Adventures of Elmo in Grouchland | EN | $11,683,047 | $11,683,047 |
| 8 | Three to Tango | EN | $10,570,375 | $10,570,375 |
| 9 | Mystery, Alaska | EN | $8,891,623 | $8,891,623 |
| 10 | Crazy in Alabama | EN | $2,005,840 | $2,005,840 |
| 11 | Happy, Texas | EN | $1,955,933 | $1,955,933 |
| 12 | Me Myself I | EN | $369,975 | $369,975 |
| 13 | The Big Tease | EN | $187,152 | $187,152 |
| 14 | Matroni and Me | EN | $130,572 | $130,572 |
| 15 | Whiteboyz | EN | $38,738 | $38,738 |
| 16 | Across a Gold Prairie |  JP | - | $38,403 |
| 17 | Captain Pantoja and the Special Services |  ES | - | $38,380 |
| 18 | Man of the Century | EN | $34,857 | $34,857 |
| 19 | Molly | EN | $17,650 | $17,650 |
| 20 | Soft Fruit | EN | $13,654 | $13,654 |
| 21 | The Suburbans | EN | $11,130 | $11,130 |
| 22 | All My Loved Ones |  CS | $6,237 | $6,237 |
| 23 | Let It Snow | EN | - | $4,020 |
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