Top Grossing Comedy Movies in December 1999
| Rank | Title | Language | Domestic | Worldwide |
|---|---|---|---|---|
| 1 | Stuart Little |  EN | $140,035,367 | $300,135,367 |
| 2 | Anna and the King | EN | $39,263,420 | $113,996,937 |
| 3 | Deuce Bigalow: Male Gigolo | EN | $65,538,755 | $92,938,755 |
| 4 | Galaxy Quest | EN | $71,583,916 | $90,685,205 |
| 5 | Man on the Moon | EN | $34,607,430 | $47,434,430 |
| 6 | Play It to the Bone | EN | $8,434,146 | $8,678,812 |
| 7 | Topsy-Turvy | EN | $6,208,548 | $7,804,439 |
| 8 | Sweet and Lowdown | EN | $4,197,015 | $4,525,794 |
| 9 | Holy Smoke | EN | $1,765,545 | $1,765,545 |
| 10 | Simpatico | EN | $929,606 | $1,281,813 |
| 11 | Agnes Browne | EN | $148,853 | $148,853 |
| 12 | Diamonds | EN | $88,428 | $88,428 |
| 13 | Diamonds | EN | $88,428 | $88,428 |
| 14 | Diamonds | EN | $88,428 | $88,428 |
| 15 | Diamonds | EN | $88,428 | $88,428 |
| 16 | Diamonds | EN | $88,428 | $88,428 |
| 17 | Diamonds | EN | $88,428 | $88,428 |
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