Top Grossing Romance Movies in October 1999
| Rank | Title | Language | Domestic | Worldwide |
|---|---|---|---|---|
| 1 | Random Hearts |  EN | $31,502,583 | $74,608,570 |
| 2 | The Story of Us | EN | $27,100,031 | $58,900,031 |
| 3 | Being John Malkovich | EN | $22,863,596 | $23,106,795 |
| 4 | Drive Me Crazy | EN | $17,845,337 | $22,593,409 |
| 5 | The Legend of 1900 | EN | $167,435 | $21,061,339 |
| 6 | Boys Don't Cry | EN | $11,540,607 | $11,540,607 |
| 7 | Three to Tango | EN | $10,570,375 | $10,570,375 |
| 8 | The Road Home |  CN | $1,280,490 | $6,780,490 |
| 9 | Beyond the Clouds | EN | $2,053,648 | $2,053,648 |
| 10 | Happy, Texas | EN | $1,955,933 | $1,955,933 |
| 11 | Gloomy Sunday |  DE | $585,604 | $646,532 |
| 12 | Grey Owl | EN | $632,617 | $632,617 |
| 13 | Me Myself I | EN | $369,975 | $369,975 |
| 14 | Show Me Love |  SE | $169,331 | $219,331 |
| 15 | Across a Gold Prairie |  JP | - | $38,403 |
| 16 | Man of the Century | EN | $34,857 | $34,857 |
| 17 | Molly | EN | $17,650 | $17,650 |
| 18 | Dreaming of Joseph Lees | EN | $12,044 | $12,044 |
| 19 | Let It Snow | EN | - | $4,020 |
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