| Rank
| Release
| Days to Milestone
| Gross-To-Date
| Date
| Total Gross
| Date
| Distributor
|
|---|
| 401 | Three Men and a Baby | 129 | $154,016,880 | Apr 1, 1988 | $167,780,960 | Nov 25, 1987 | Walt Disney Studios Motion Pictures |
| 402 | Rambo: First Blood Part II | 129 | $150,415,432 | Sep 27, 1985 | $150,415,432 | May 22, 1985 | TriStar Pictures |
| 403 | Indiana Jones and the Temple of Doom | 135 | $172,581,621 | Oct 4, 1984 | $179,870,271 | May 23, 1984 | Paramount Pictures |
| 404 | Scary Movie | 137 | $157,019,771 | Nov 20, 2000 | $157,019,771 | Jul 7, 2000 | Miramax |
| 405 | Jerry Maguire | 141 | $150,030,328 | May 2, 1997 | $153,952,592 | Dec 13, 1996 | Sony Pictures Releasing |
| 406 | The Waterboy | 147 | $161,297,817 | Apr 1, 1999 | $161,491,646 | Nov 6, 1998 | Walt Disney Studios Motion Pictures |
| 407 | Austin Powers: The Spy Who Shagged Me | 149 | $205,904,385 | Nov 4, 1999 | $206,040,086 | Jun 9, 1999 | New Line Cinema |
| 408 | Ghost | 151 | $200,000,000 | Dec 10, 1990 | $217,631,306 | Jul 13, 1990 | Paramount Pictures |
| 409 | Who Framed Roger Rabbit | 162 | $156,452,370 | Dec 2, 1988 | $156,452,370 | Jun 24, 1988 | Walt Disney Studios Motion Pictures |
| 410 | Runaway Bride | 165 | $152,257,509 | Jan 10, 2000 | $152,257,509 | Jul 30, 1999 | Paramount Pictures |
| 411 | There's Something About Mary | 170 | $174,422,745 | Dec 31, 1998 | $176,484,651 | Jul 15, 1998 | Twentieth Century Fox |
| 412 | Rain Man | 176 | $172,825,435 | Jun 9, 1989 | $172,825,435 | Dec 16, 1988 | Metro-Goldwyn-Mayer (MGM) |
| 413 | The Fugitive | 182 | $179,414,162 | Feb 3, 1994 | $183,875,760 | Aug 6, 1993 | Warner Bros. |
| 414 | Crocodile Dundee | 188 | $159,398,373 | Apr 1, 1987 | $174,803,506 | Sep 26, 1986 | Paramount Pictures |
| 415 | Pretty Woman | 196 | $173,961,751 | Oct 4, 1990 | $178,406,268 | Mar 23, 1990 | Walt Disney Studios Motion Pictures |
| 416 | Tarzan | 198 | $170,867,780 | Dec 30, 1999 | $171,091,819 | Jun 16, 1999 | Walt Disney Studios Motion Pictures |
| 417 | Tootsie | 201 | $177,200,000 | Jul 5, 1983 | $177,200,000 | Dec 17, 1982 | Columbia Pictures |
| 418 | Raiders of the Lost Ark | 210 | $177,733,831 | Jan 7, 1982 | $212,222,025 | Jun 12, 1981 | Paramount Pictures |
| 419 | Dances with Wolves | 210 | $175,563,065 | Jun 20, 1991 | $184,208,848 | Nov 23, 1990 | Orion Pictures |
| 420 | Fatal Attraction | 210 | $151,839,068 | Apr 14, 1988 | $156,645,693 | Sep 18, 1987 | Paramount Pictures |
| 421 | Top Gun | 211 | $176,781,728 | Dec 12, 1986 | $176,781,728 | May 16, 1986 | Paramount Pictures |
| 422 | Star Wars: Episode VI - Return of the Jedi | 212 | $244,961,102 | Dec 22, 1983 | $252,583,617 | May 25, 1983 | Twentieth Century Fox |
| 423 | The Exorcist | 731 | $193,000,000 | Dec 26, 1975 | $193,000,000 | Dec 26, 1973 | Warner Bros. |
| 424 | The Sting | 731 | $156,000,000 | Dec 25, 1975 | $156,000,000 | Dec 25, 1973 | Universal Pictures |
