| Rank
| Title
| Lifetime Gross | Max Theaters | Opening | Open Th | Release Date | Distributor
|
|---|
| 301 | Whatever It Takes | $8,745,680 | 2,272 | $4,104,298 | 2,272 | Mar 24, 2000 | Sony Pictures Releasing |
| 302 | My Life in Ruins | $8,665,206 | 1,165 | $3,223,161 | 1,164 | Jun 5, 2009 | - |
| 303 | Secret Admirer | $8,622,757 | 1,300 | $2,414,984 | 1,300 | Jun 14, 1985 | Orion Pictures |
| 304 | Boat Trip | $8,600,126 | 1,803 | $3,700,000 | 1,714 | Mar 21, 2003 | Artisan Entertainment |
| 305 | High Spirits | $8,578,231 | 826 | $3,308,250 | 825 | Nov 18, 1988 | TriStar Pictures |
| 306 | Something Wild | $8,362,969 | 916 | $1,825,717 | 914 | Nov 7, 1986 | Orion Pictures |
| 307 | The Love Letter | $8,302,478 | 817 | $2,692,819 | 769 | May 21, 1999 | DreamWorks Distribution |
| 308 | Funny About Love | $8,141,292 | 1,213 | $3,036,352 | 1,213 | Sep 21, 1990 | Paramount Pictures |
| 309 | Woo | $8,064,972 | 625 | $2,517,263 | 625 | May 8, 1998 | New Line Cinema |
| 310 | Strictly Business | $7,683,267 | 881 | $2,456,772 | 881 | Nov 8, 1991 | Warner Bros. |
| 311 | Sprung | $7,575,028 | 780 | $2,487,702 | 780 | May 16, 1997 | Trimark Pictures |
| 312 | Over Her Dead Body | $7,563,670 | 1,977 | $4,600,000 | 1,977 | Feb 1, 2008 | New Line Cinema |
| 313 | A Good Year | $7,459,300 | 2,067 | $3,721,526 | 2,066 | Nov 10, 2006 | Twentieth Century Fox |
| 314 | She's So Lovely | $7,281,450 | 844 | $3,020,015 | 824 | Aug 27, 1997 | Miramax |
| 315 | Barcelona | $7,266,973 | 274 | $102,820 | 4 | Jul 29, 1994 | Fine Line Features |
| 316 | She's Gotta Have It | $7,137,502 | 1 | $28,473 | 1 | Aug 8, 1986 | Island Pictures |
| 317 | Kissing Jessica Stein | $7,025,722 | 319 | $346,999 | 26 | Mar 13, 2002 | - |
| 318 | Romantic Comedy | $6,857,733 | 911 | $2,366,025 | 911 | Oct 7, 1983 | Metro-Goldwyn-Mayer (MGM) |
| 319 | Town & Country | $6,719,973 | 2,222 | $3,029,858 | 2,222 | Apr 27, 2001 | New Line Cinema |
| 320 | Mighty Aphrodite | $6,468,498 | 278 | $326,494 | 19 | Oct 27, 1995 | Miramax |
| 321 | Mystery Date | $6,166,819 | 1,371 | $1,952,569 | 1,371 | Aug 16, 1991 | Orion Pictures |
| 322 | Chasing Papi | $6,130,049 | 585 | $2,404,557 | 585 | Apr 16, 2003 | Twentieth Century Fox |
| 323 | Gigli | $6,087,542 | 2,215 | $3,753,518 | 2,215 | Aug 1, 2003 | Revolution Studios |
| 324 | The Opposite of Sex | $5,881,367 | 165 | $102,385 | 5 | May 22, 1998 | Sony Pictures Classics |
| 325 | Pulling Strings | $5,842,961 | 438 | $2,467,168 | 387 | Oct 4, 2013 | Lionsgate |
| 326 | The Pallbearer | $5,656,388 | 829 | $2,319,236 | 829 | May 3, 1996 | Miramax |
| 327 | Paris Can Wait | $5,617,731 | 447 | $98,850 | 4 | May 12, 2017 | Sony Pictures Classics |
| 328 | Say It Isn't So | $5,520,393 | 1,974 | $2,861,903 | 1,974 | Mar 23, 2001 | Twentieth Century Fox |
| 329 | Three of Hearts | $5,495,507 | 793 | $1,928,076 | 792 | Apr 30, 1993 | New Line Cinema |
| 330 | Creator | $5,349,607 | 820 | $2,019,728 | 820 | Sep 20, 1985 | Universal Pictures |
| 331 | Miami Rhapsody | $5,221,281 | 180 | $71,421 | 2 | Jan 27, 1995 | Walt Disney Studios Motion Pictures |
| 332 | American Dreamer | $5,021,751 | 801 | $1,580,990 | 801 | Oct 26, 1984 | Warner Bros. |
| 333 | Woman on Top | $5,020,111 | 1,086 | $2,008,191 | 1,085 | Sep 22, 2000 | - |
| 334 | No Small Affair | $4,994,094 | 1,247 | $2,273,469 | 1,247 | Nov 9, 1984 | Columbia Pictures |
| 335 | Summer Lovers | $4,968,000 | - | - | - | Jul 16, 1982 | - |
| 336 | Simply Irresistible | $4,398,989 | 1,359 | $2,232,686 | 1,359 | Feb 5, 1999 | Twentieth Century Fox |
| 337 | A Life Less Ordinary | $4,366,722 | 1,208 | $2,007,279 | 1,207 | Oct 24, 1997 | Twentieth Century Fox |
| 338 | On the Line | $4,365,455 | 901 | $2,307,063 | 900 | Oct 26, 2001 | Miramax |
| 339 | Kissing a Fool | $4,106,588 | 1,754 | $2,308,145 | 1,742 | Feb 27, 1998 | Universal Pictures |
| 340 | Man Trouble | $4,096,030 | 1,009 | $2,034,475 | 1,009 | Jul 17, 1992 | Twentieth Century Fox |
| 341 | Loverboy | $3,960,327 | 1,089 | $1,653,102 | 1,089 | Apr 28, 1989 | TriStar Pictures |
| 342 | The Heavenly Kid | $3,852,271 | 1,019 | $1,614,225 | 1,019 | Jul 26, 1985 | Orion Pictures |
| 343 | Mannequin: On the Move | $3,752,428 | 1,540 | $1,692,817 | 1,540 | May 17, 1991 | Twentieth Century Fox |
| 344 | The Jane Austen Book Club | $3,575,227 | 1,232 | $148,549 | 25 | Sep 21, 2007 | Sony Pictures Classics |
| 345 | 'Til There Was You | $3,525,125 | 753 | $1,315,445 | 753 | May 30, 1997 | Paramount Pictures |
| 346 | What If | $3,493,000 | 787 | $133,898 | 20 | Aug 8, 2014 | CBS Films |
| 347 | Juliet, Naked | $3,444,895 | 467 | $60,886 | 4 | Aug 17, 2018 | Roadside Attractions |
| 348 | Next Stop Wonderland | $3,395,581 | 224 | $123,055 | 8 | Aug 21, 1998 | Miramax |
| 349 | The MatchMaker | $3,392,080 | 705 | $1,378,930 | 705 | Oct 3, 1997 | Gramercy Pictures (I) |
| 350 | Anything Else | $3,212,310 | 1,033 | $1,673,125 | 1,033 | Sep 19, 2003 | DreamWorks Distribution |
| 351 | The Favor | $3,134,381 | 1,029 | $1,487,238 | 1,029 | Apr 29, 1994 | Orion Pictures |
| 352 | Boynton Beach Club | $3,127,472 | 65 | $63,422 | 11 | Mar 17, 2006 | - |
| 353 | Mr. Wonderful | $3,125,424 | 720 | $1,177,311 | 720 | Oct 15, 1993 | Warner Bros. |
| 354 | Obvious Child | $3,123,963 | 202 | $77,315 | 3 | Jun 6, 2014 | A24 |
| 355 | The Guru | $3,095,506 | 98 | $613,485 | 62 | Jan 31, 2003 | Universal Pictures |
| 356 | The Ex | $3,093,394 | 1,009 | $1,394,229 | 1,009 | May 11, 2007 | - |
| 357 | Tanu Weds Manu Returns | $3,043,479 | 136 | $1,006,476 | 136 | May 22, 2015 | Eros Worldwide |
| 358 | From Prada to Nada | $3,033,623 | 261 | $1,115,638 | 256 | Jan 28, 2011 | Lionsgate |
| 359 | Tadpole | $2,891,288 | 180 | $80,682 | 6 | Jul 19, 2002 | Miramax |
| 360 | Modern Romance | $2,863,642 | 1 | $18,225 | 1 | Mar 13, 1981 | Columbia Pictures |
| 361 | The Perez Family | $2,832,826 | 928 | $1,127,645 | 928 | May 12, 1995 | The Samuel Goldwyn Company |
| 362 | Year of the Comet | $2,791,515 | 1,006 | $1,350,939 | 1,001 | Apr 24, 1992 | Columbia Pictures |
| 363 | La boda de Valentina | $2,783,739 | 331 | $1,147,073 | 331 | Feb 9, 2018 | Pantelion Films |
| 364 | Tod@s caen | $2,670,925 | 371 | $1,098,401 | 371 | Aug 30, 2019 | Pantelion Films |
| 365 | Qué León | $2,607,916 | 86 | $291,936 | 34 | Nov 29, 2018 | Spanglish Movies |
| 366 | Ruby Sparks | $2,540,106 | 261 | $140,822 | 13 | Jul 25, 2012 | - |
| 367 | The Black Marble | $2,500,000 | - | - | - | Jan 1, 1980 | AVCO Embassy Pictures |
| 368 | If Lucy Fell | $2,420,162 | 1,200 | $1,308,088 | 1,200 | Mar 8, 1996 | Sony Pictures Releasing |
| 369 | Sidewalks of New York | $2,402,652 | 224 | $545,132 | 99 | Nov 23, 2001 | Paramount Classics |
| 370 | A Little Sex | $2,370,376 | 550 | $1,030,070 | 500 | Apr 2, 1982 | Universal Pictures |
| 371 | Hav Plenty | $2,284,034 | 413 | $1,102,036 | 413 | Jun 19, 1998 | Miramax |
| 372 | Dans une galaxie près de chez vous - Le film | $2,259,688 | 74 | - | - | Apr 9, 2004 | - |
| 373 | The Incredibly True Adventure of Two Girls in Love | $2,210,408 | - | - | - | Jun 16, 1995 | Fine Line Features |
| 374 | The Lovers | $2,194,521 | 443 | $66,286 | 4 | May 5, 2017 | A24 |
| 375 | Austenland | $2,159,041 | 274 | $40,662 | 4 | Aug 16, 2013 | Sony Pictures Classics |
| 376 | Trick | $2,087,228 | 94 | $118,594 | 6 | Jul 23, 1999 | Fine Line Features |
| 377 | Just Tell Me What You Want | $2,086,905 | 49 | $197,230 | 49 | Feb 8, 1980 | Warner Bros. |
| 378 | Billy's Hollywood Screen Kiss | $2,070,399 | - | - | - | Jul 24, 1998 | Trimark Pictures |
| 379 | Married to It | $2,059,832 | 822 | $1,077,278 | 822 | Mar 26, 1993 | Orion Pictures |
| 380 | Better Than Chocolate | $2,015,406 | 130 | $84,584 | 15 | Aug 13, 1999 | Trimark Pictures |
| 381 | The Bride of Badrinath | $1,993,259 | 156 | $862,008 | 152 | Mar 10, 2017 | FIP |
| 382 | Date with an Angel | $1,988,962 | 843 | $816,062 | 843 | Nov 20, 1987 | De Laurentiis Entertainment Group (DEG) |
| 383 | Everybody Loves Somebody | $1,915,789 | 333 | $924,201 | 333 | Feb 17, 2017 | Pantelion Films |
| 384 | The Night We Never Met | $1,884,814 | 504 | $911,736 | 504 | Apr 30, 1993 | Miramax |
| 385 | The Slugger's Wife | $1,878,561 | 898 | $1,314,993 | 898 | Mar 29, 1985 | Columbia Pictures |
| 386 | The Five of Us | $1,852,272 | 45 | $281,606 | 45 | Aug 27, 2004 | Alliance Atlantis Vivafilm |
| 387 | Hysteria | $1,804,139 | 218 | $35,656 | 5 | May 18, 2012 | Sony Pictures Classics |
| 388 | Tune in Tomorrow... | $1,794,001 | 207 | $62,747 | 7 | Oct 26, 1990 | Cinecom Pictures |
| 389 | The Broken Hearts Club: A Romantic Comedy | $1,746,585 | 62 | $109,694 | 7 | Sep 29, 2000 | Sony Pictures Classics |
| 390 | Jab Harry Met Sejal | $1,664,648 | 280 | $1,284,740 | 280 | Aug 4, 2017 | Yash Raj Films |
| 391 | Gun Shy | $1,638,202 | 296 | $703,109 | 296 | Feb 4, 2000 | Walt Disney Studios Motion Pictures |
| 392 | Love Is All You Need | $1,631,709 | 101 | $36,746 | 4 | May 3, 2013 | Sony Pictures Classics |
| 393 | Trust the Man | $1,530,535 | 260 | $180,271 | 38 | Aug 18, 2006 | - |
| 394 | Bollywood/Hollywood | $1,454,510 | 44 | - | - | Oct 25, 2002 | - |
| 395 | Monica la mitraille | $1,435,015 | 99 | $323,752 | 99 | Apr 30, 2004 | Alliance Atlantis Vivafilm |
| 396 | The Wedding Plan | $1,412,404 | 123 | $31,658 | 8 | May 12, 2017 | Roadside Attractions |
| 397 | It's Not You, It's Me | $1,339,911 | 226 | $588,938 | 226 | Apr 8, 2011 | Lionsgate |
| 398 | Housefull 3 | $1,326,999 | 145 | $683,620 | 145 | Jun 3, 2016 | Eros Worldwide |
| 399 | Walking and Talking | $1,287,480 | - | - | - | Jul 17, 1996 | Miramax |
| 400 | The Singles Ward | $1,250,798 | 29 | $43,149 | 11 | Feb 1, 2002 | - |
