Top Grossing Romance Movies in 1999
| Rank | Title | Language | Domestic | Worldwide |
|---|---|---|---|---|
| 1 | Notting Hill |  EN | $116,089,678 | $364,003,519 |
| 2 | Runaway Bride | EN | $152,257,509 | $309,460,292 |
| 3 | American Pie | EN | $102,561,004 | $235,483,004 |
| 4 | Entrapment | EN | $87,704,396 | $212,404,396 |
| 5 | Eyes Wide Shut | EN | $55,691,208 | $162,390,519 |
| 6 | The Talented Mr. Ripley | EN | $81,298,265 | $138,034,667 |
| 7 | The Thomas Crown Affair | EN | $69,305,181 | $124,305,181 |
| 8 | Message in a Bottle | EN | $52,880,016 | $118,880,016 |
| 9 | Anna and the King | EN | $39,263,420 | $113,996,937 |
| 10 | She's All That | EN | $63,366,989 | $103,166,989 |
| 11 | Forces of Nature | EN | $52,900,680 | $93,900,680 |
| 12 | The Cider House Rules | EN | $57,545,092 | $88,545,092 |
| 13 | Bicentennial Man | EN | $58,223,861 | $87,423,861 |
| 14 | Never Been Kissed | EN | $55,474,756 | $84,565,230 |
| 15 | Out of Season | EN | $37,562,568 | $77,745,966 |
| 16 | Cruel Intentions | EN | $38,773,785 | $76,347,426 |
| 17 | Random Hearts | EN | $31,502,583 | $74,608,570 |
| 18 | The Story of Us | EN | $27,100,031 | $58,900,031 |
| 19 | Varsity Blues | EN | $52,894,169 | $54,294,169 |
| 20 | Mickey Blue Eyes | EN | $33,864,342 | $54,264,342 |
| 21 | 10 Things I Hate About You | EN | $38,178,166 | $53,683,812 |
| 22 | For Love of the Game | EN | $35,188,640 | $46,112,640 |
| 23 | Blast from the Past | EN | $26,511,114 | $40,263,020 |
| 24 | The Bachelor | EN | $21,760,240 | $36,911,617 |
| 25 | The Other Sister | EN | $27,807,627 | $27,807,627 |
| 26 | The Wood | EN | $25,059,640 | $25,059,640 |
| 27 | Being John Malkovich | EN | $22,863,596 | $23,106,795 |
| 28 | Snow Falling on Cedars | EN | $14,417,593 | $23,049,593 |
| 29 | Drive Me Crazy | EN | $17,845,337 | $22,593,409 |
| 30 | At First Sight | EN | $22,365,133 | $22,365,133 |
| 31 | The Legend of 1900 | EN | $167,435 | $21,061,339 |
| 32 | Summer of Sam | EN | $19,288,130 | $19,288,130 |
| 33 | The Thirteenth Floor | EN | $11,916,661 | $18,564,088 |
| 34 | An Ideal Husband | EN | $18,542,974 | $18,542,974 |
| 35 | A Midsummer Night's Dream | EN | $16,071,990 | $16,071,990 |
| 36 | Election |  CN | $14,902,041 | $14,902,280 |
| 37 | Boys Don't Cry | EN | $11,540,607 | $11,540,607 |
| 38 | Office Space | EN | $10,827,810 | $10,829,894 |
| 39 | The End of the Affair | EN | $10,827,816 | $10,827,816 |
| 40 | Three to Tango | EN | $10,570,375 | $10,570,375 |
| 41 | The Red Violin | EN | $10,019,109 | $10,019,109 |
| 42 | Dudley Do-Right | EN | $9,974,410 | $9,974,410 |
| 43 | The Love Letter | EN | $8,302,478 | $9,139,145 |
| 44 | Trippin’ | EN | $9,017,070 | $9,017,070 |
| 45 | Outside Providence | EN | $7,302,522 | $7,302,522 |
| 46 | 200 Cigarettes | CN | $6,852,450 | $6,852,450 |
| 47 | The Road Home | CN | $1,280,490 | $6,780,490 |
| 48 | Lost & Found |  ES | $6,552,255 | $6,552,255 |
| 49 | East/West |  FR | $2,321,029 | $6,031,521 |
| 50 | Mansfield Park | EN | $4,775,847 | $4,775,847 |
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