| Rank
| Title
| Lifetime Gross | Max Theaters | Opening | Open Th | Release Date | Distributor
|
|---|
| 201 | Two Can Play That Game | $22,235,901 | 1,308 | $7,720,942 | 1,297 | Sep 7, 2001 | Screen Gems |
| 202 | Emma | $22,231,658 | 848 | $240,649 | 9 | Aug 2, 1996 | Miramax |
| 203 | Don Juan DeMarco | $22,150,451 | 1,226 | $4,556,274 | 1,110 | Apr 7, 1995 | New Line Cinema |
| 204 | Cousins | $22,026,369 | 747 | $3,039,805 | 535 | Feb 10, 1989 | Paramount Pictures |
| 205 | Love Don't Cost a Thing | $21,924,226 | 1,844 | $6,315,311 | 1,844 | Dec 12, 2003 | Warner Bros. |
| 206 | A Lot Like Love | $21,845,719 | 2,502 | $7,576,593 | 2,502 | Apr 22, 2005 | Walt Disney Studios Motion Pictures |
| 207 | Only the Lonely | $21,830,957 | 1,553 | $5,997,993 | 1,521 | May 24, 1991 | Twentieth Century Fox |
| 208 | The Big Wedding | $21,819,348 | 2,633 | $7,591,663 | 2,633 | Apr 26, 2013 | Lionsgate |
| 209 | Boys and Girls | $21,799,652 | 1,989 | $7,008,950 | 1,983 | Jun 16, 2000 | Dimension Films |
| 210 | The Bachelor | $21,760,240 | 2,524 | $7,480,288 | 2,522 | Nov 5, 1999 | New Line Cinema |
| 211 | Baggage Claim | $21,569,509 | 2,230 | $9,031,102 | 2,027 | Sep 27, 2013 | - |
| 212 | Just Wright | $21,540,363 | 1,831 | $8,284,989 | 1,831 | May 14, 2010 | - |
| 213 | Married to the Mob | $21,486,757 | 828 | $3,231,056 | 824 | Aug 19, 1988 | Orion Pictures |
| 214 | Straight Talk | $21,202,099 | 1,477 | $4,575,746 | 1,477 | Apr 3, 1992 | Walt Disney Studios Motion Pictures |
| 215 | Reality Bites | $20,982,557 | 1,175 | $5,113,050 | 1,149 | Feb 18, 1994 | Universal Pictures |
| 216 | Say Anything | $20,781,385 | 1,113 | $4,058,496 | 1,113 | Apr 14, 1989 | Twentieth Century Fox |
| 217 | Little Black Book | $20,698,668 | 2,445 | $7,075,217 | 2,445 | Aug 6, 2004 | Revolution Studios |
| 218 | Speechless | $20,667,959 | 1,404 | $3,969,048 | 1,404 | Dec 16, 1994 | Metro-Goldwyn-Mayer (MGM) |
| 219 | Hello Again | $20,419,446 | 1,207 | $5,712,892 | 1,201 | Nov 6, 1987 | Walt Disney Studios Motion Pictures |
| 220 | Down with Love | $20,305,251 | 2,123 | $45,029 | 1 | May 9, 2003 | Twentieth Century Fox |
| 221 | Down to You | $20,069,008 | 2,003 | $7,602,507 | 1,971 | Jan 21, 2000 | Miramax |
| 222 | Only You | $20,059,210 | 1,617 | $5,711,738 | 1,600 | Oct 7, 1994 | TriStar Pictures |
| 223 | Prelude to a Kiss | $20,006,730 | 1,248 | $5,273,395 | 1,247 | Jul 10, 1992 | Twentieth Century Fox |
| 224 | Unfaithfully Yours | $19,928,200 | 831 | $3,774,126 | 820 | Feb 10, 1984 | Twentieth Century Fox |
| 225 | Summer Catch | $19,753,553 | 2,335 | $7,018,593 | 2,335 | Aug 24, 2001 | Warner Bros. |
| 226 | My Best Friend's Girl | $19,219,250 | 2,636 | $8,265,357 | 2,604 | Sep 19, 2008 | Lionsgate |
| 227 | Waitress | $19,074,800 | 707 | $92,034 | 4 | May 2, 2007 | - |
| 228 | Her Alibi | $18,699,037 | 1,429 | $5,037,047 | 1,429 | Feb 3, 1989 | Warner Bros. |
| 229 | Blame It on Rio | $18,644,570 | 1,234 | $3,437,660 | 1,201 | Feb 17, 1984 | Twentieth Century Fox |
| 230 | Singles | $18,471,850 | 1,330 | $4,184,875 | 1,073 | Sep 18, 1992 | Warner Bros. |
| 231 | Milk Money | $18,137,661 | 1,361 | $5,846,533 | 1,361 | Sep 2, 1994 | Paramount Pictures |
| 232 | The Sure Thing | $18,135,531 | 1,115 | $3,124,782 | 1,115 | Mar 1, 1985 | Metro-Goldwyn-Mayer (MGM) |
| 233 | Born Yesterday | $17,952,857 | 1,301 | $5,911,343 | 1,297 | Mar 26, 1993 | Walt Disney Studios Motion Pictures |
| 234 | Laws of Attraction | $17,871,255 | 2,449 | $7,000,000 | 2,449 | Apr 30, 2004 | New Line Cinema |
| 235 | Drive Me Crazy | $17,845,337 | 2,233 | $6,846,112 | 2,222 | Oct 1, 1999 | Twentieth Century Fox |
| 236 | Punch-Drunk Love | $17,844,216 | 1,293 | $367,203 | 5 | Oct 11, 2002 | Revolution Studios |
| 237 | Going the Distance | $17,804,299 | 3,030 | $6,884,964 | 3,030 | Sep 3, 2010 | Warner Bros. |
| 238 | Deliver Us from Eva | $17,573,594 | 1,139 | $7,100,000 | 1,139 | Feb 7, 2003 | Focus Features |
| 239 | Valley Girl | $17,343,596 | 442 | $1,856,780 | 442 | Apr 29, 1983 | Atlantic Releasing Corporation |
| 240 | Just My Luck | $17,326,650 | 2,543 | $5,692,285 | 2,541 | May 12, 2006 | Twentieth Century Fox |
| 241 | Win a Date with Tad Hamilton! | $17,071,962 | 2,808 | $7,320,066 | 2,711 | Jan 23, 2004 | DreamWorks Distribution |
| 242 | Wimbledon | $17,001,133 | 2,039 | $7,118,985 | 2,034 | Sep 17, 2004 | Universal Pictures |
| 243 | Serving Sara | $16,930,185 | 2,174 | $5,758,236 | 2,154 | Aug 23, 2002 | Paramount Pictures |
| 244 | The One and Only | $16,928,137 | - | - | - | Feb 2, 1978 | Paramount Pictures |
| 245 | New in Town | $16,734,283 | 1,941 | $6,741,530 | 1,941 | Jan 30, 2009 | Lionsgate |
| 246 | That Old Feeling | $16,574,176 | 1,599 | $5,103,075 | 1,575 | Apr 4, 1997 | Universal Pictures |
| 247 | The Perfect Man | $16,535,005 | 2,090 | $5,300,980 | 2,087 | Jun 17, 2005 | Universal Pictures |
| 248 | Chances Are | $16,278,590 | 1,190 | $3,664,386 | 837 | Mar 10, 1989 | TriStar Pictures |
| 249 | Crossing Delancey | $16,262,415 | 303 | $46,711 | 1 | Aug 26, 1988 | Warner Bros. |
| 250 | A Midsummer Night's Dream | $16,071,990 | 1,099 | $4,285,620 | 1,080 | May 14, 1999 | - |
| 251 | Loser | $15,618,626 | 2,016 | $6,008,611 | 2,016 | Jul 21, 2000 | Sony Pictures Releasing |
| 252 | Continental Divide | $15,578,237 | 864 | $3,218,347 | 864 | Sep 18, 1981 | Universal Pictures |
| 253 | A Guy Thing | $15,545,431 | 2,520 | $6,988,749 | 2,515 | Jan 17, 2003 | Metro-Goldwyn-Mayer (MGM) |
| 254 | Catch and Release | $15,539,051 | 1,622 | $7,658,898 | 1,622 | Jan 26, 2007 | Sony Pictures Releasing |
| 255 | About Time | $15,322,921 | 1,280 | $1,076,250 | 175 | Nov 1, 2013 | Universal Pictures |
| 256 | Threesome | $14,815,317 | 1,218 | $4,001,024 | 1,212 | Apr 8, 1994 | TriStar Pictures |
| 257 | Arthur 2: On the Rocks | $14,681,192 | 1,426 | $5,150,962 | 1,426 | Jul 8, 1988 | Warner Bros. |
| 258 | Life or Something Like It | $14,448,589 | 2,609 | $6,219,234 | 2,606 | Apr 26, 2002 | Twentieth Century Fox |
| 259 | Alex & Emma | $14,218,698 | 2,310 | $6,111,074 | 2,310 | Jun 20, 2003 | Warner Bros. |
| 260 | Ghost Town | $13,367,624 | 1,512 | $5,012,315 | 1,505 | Sep 19, 2008 | DreamWorks |
| 261 | The Pick-up Artist | $13,290,368 | 1,132 | $4,455,516 | 1,129 | Sep 18, 1987 | Twentieth Century Fox |
| 262 | Dr. T & the Women | $13,113,041 | 1,489 | $5,012,867 | 1,489 | Oct 13, 2000 | Artisan Entertainment |
| 263 | Playing for Keeps | $13,103,272 | 2,840 | $5,750,288 | 2,837 | Dec 7, 2012 | FilmDistrict |
| 264 | Mr. Wrong | $12,825,141 | 1,487 | $5,106,797 | 1,487 | Feb 16, 1996 | Walt Disney Studios Motion Pictures |
| 265 | Mystic Pizza | $12,793,213 | 440 | $1,163,939 | 401 | Oct 21, 1988 | The Samuel Goldwyn Company |
| 266 | I Think I Love My Wife | $12,550,605 | 1,794 | $5,674,802 | 1,776 | Mar 16, 2007 | - |
| 267 | The Marrying Man | $12,454,768 | 1,343 | $4,030,749 | 1,340 | Apr 5, 1991 | Walt Disney Studios Motion Pictures |
| 268 | True Romance | $12,281,551 | 1,254 | $4,023,420 | 1,254 | Sep 10, 1993 | Warner Bros. |
| 269 | Breakin' All the Rules | $12,264,319 | 1,318 | $5,088,577 | 1,318 | May 14, 2004 | Screen Gems |
| 270 | Chasing Liberty | $12,195,626 | 2,400 | $6,081,483 | 2,400 | Jan 9, 2004 | Warner Bros. |
| 271 | Bye Bye Love | $12,096,673 | 1,379 | $4,523,048 | 1,378 | Mar 17, 1995 | Twentieth Century Fox |
| 272 | Chasing Amy | $12,021,272 | 553 | $52,446 | 3 | Apr 4, 1997 | Miramax |
| 273 | Sliding Doors | $11,841,544 | 522 | $834,817 | 117 | Apr 24, 1998 | Miramax |
| 274 | The Last Kiss | $11,614,790 | 1,359 | $4,627,989 | 1,357 | Sep 15, 2006 | DreamWorks |
| 275 | So I Married an Axe Murderer | $11,585,483 | 1,355 | $3,466,930 | 1,349 | Jul 30, 1993 | TriStar Pictures |
| 276 | Get Over It | $11,576,464 | 1,742 | $4,134,977 | 1,742 | Mar 9, 2001 | Miramax |
| 277 | The Beautician and the Beast | $11,486,880 | 1,801 | $4,080,222 | 1,801 | Feb 7, 1997 | Paramount Pictures |
| 278 | Something New | $11,468,568 | 1,265 | $5,016,000 | 1,265 | Feb 3, 2006 | Focus Features |
| 279 | Career Opportunities | $11,336,986 | 1,440 | $4,024,800 | 1,440 | Mar 29, 1991 | Universal Pictures |
| 280 | For Love or Money | $11,146,270 | 1,644 | $4,016,220 | 1,626 | Oct 1, 1993 | Universal Pictures |
| 281 | Mad Dog and Glory | $11,081,586 | 1,118 | $3,815,555 | 1,098 | Mar 5, 1993 | Universal Pictures |
| 282 | The Englishman Who Went Up a Hill But Came Down a Mountain | $10,904,930 | 961 | $2,811,355 | 954 | May 12, 1995 | Miramax |
| 283 | Two If by Sea | $10,658,278 | 1,796 | $4,656,986 | 1,712 | Jan 12, 1996 | Warner Bros. |
| 284 | The Purple Rose of Cairo | $10,631,333 | 419 | $114,095 | 3 | Mar 1, 1985 | Orion Pictures |
| 285 | Three to Tango | $10,570,375 | 2,234 | $4,406,135 | 2,234 | Oct 22, 1999 | Warner Bros. |
| 286 | Husbands and Wives | $10,555,619 | 868 | $3,520,550 | 865 | Sep 18, 1992 | TriStar Pictures |
| 287 | Magic in the Moonlight | $10,539,326 | 964 | $412,095 | 17 | Jul 25, 2014 | Sony Pictures Classics |
| 288 | Scoop | $10,525,717 | 541 | $3,003,000 | 538 | Jul 28, 2006 | Focus Features |
| 289 | Home Fries | $10,493,366 | 1,925 | $3,784,023 | 1,925 | Nov 27, 1998 | Warner Bros. |
| 290 | Head Over Heels | $10,424,470 | 2,363 | $4,804,595 | 2,338 | Feb 2, 2001 | Universal Pictures |
| 291 | Shopgirl | $10,284,523 | 493 | $229,685 | 8 | Oct 21, 2005 | Walt Disney Studios Motion Pictures |
| 292 | Mrs. Winterbourne | $10,082,005 | 1,612 | $3,872,900 | 1,612 | Apr 19, 1996 | Sony Pictures Releasing |
| 293 | Miami Blues | $9,888,167 | 833 | $3,002,997 | 832 | Apr 20, 1990 | Orion Pictures |
| 294 | He Said, She Said | $9,804,775 | 908 | $2,857,164 | 908 | Feb 22, 1991 | Paramount Pictures |
| 295 | Everyone Says I Love You | $9,759,200 | 276 | $131,678 | 3 | Dec 6, 1996 | Miramax |
| 296 | The Butcher's Wife | $9,689,816 | 800 | $2,442,229 | 800 | Oct 25, 1991 | Paramount Pictures |
| 297 | The Perfect Match | $9,669,521 | 925 | $4,294,232 | 925 | Mar 11, 2016 | Lionsgate |
| 298 | She's the One | $9,538,948 | 464 | $2,088,492 | 459 | Aug 23, 1996 | - |
| 299 | The Divorce | $9,081,057 | 701 | $516,834 | 34 | Aug 8, 2003 | - |
| 300 | First Daughter | $9,055,921 | 2,280 | $4,002,067 | 2,260 | Sep 24, 2004 | Twentieth Century Fox |
