100 English films of 1999 ranked by box office. #1: Star Wars: Episode I – The Phantom Menace ($1 billion).
| # | Film | Lead | Director | Budget | Box office | Multiple |
|---|---|---|---|---|---|---|
| 1 | Star Wars: Episode I – The Phantom Menace | George Lucas | $115 million | $1 billion | 9.10x | |
| 2 | The Sixth Sense | M. Night Shyamalan | $40 million | $672.8 million | 16.82x | |
| 3 | The Matrix | Lilly Wachowski | $63 million | $473.3 million | 7.51x | |
| 4 | The Mummy | Stephen Sommers | $80 million | $422.5 million | 5.28x | |
| 5 | Notting Hill | Roger Michell | $42 million | $364 million | 8.67x | |
| 6 | The World Is Not Enough | Michael Apted | $135 million | $361 million | 2.67x | |
| 7 | American Beauty | Sam Mendes | $15 million | $356.3 million | 23.75x | |
| 8 | Austin Powers: The Spy Who Shagged Me | Jay Roach | $33 million | $312 million | 9.45x | |
| 9 | Runaway Bride | Garry Marshall | $70 million | $309.5 million | 4.42x | |
| 10 | Stuart Little | Rob Minkoff | $133 million | $300.1 million | 2.26x | |
| 11 | The Green Mile | Frank Darabont | $60 million | $286.8 million | 4.78x | |
| 12 | The Blair Witch Project | Eduardo Sánchez | $60,000 | $248.6 million | 4143.33x | |
| 13 | American Pie | Paul Weitz | $11 million | $235.5 million | 21.41x | |
| 14 | Big Daddy | Dennis Dugan | $34.2 million | $234.8 million | 6.87x | |
| 15 | Wild Wild West | Barry Sonnenfeld | $170 million | $222.1 million | 1.31x | |
| 16 | Entrapment | Jon Amiel | $66 million | $212 million | 3.21x | |
| 16 | End of Days | Peter Hyams | $100 million | $212 million | 2.12x | |
| 18 | Sleepy Hollow | Tim Burton | $100 million | $207 million | 2.07x | |
| 19 | The Haunting | Jan de Bont | $80 million | $180.2 million | 2.25x | |
| 20 | Double Jeopardy | Bruce Beresford | $40 million | $177.8 million | 4.45x | |
| 21 | Analyze This | Harold Ramis | $80 million | $176.9 million | 2.21x | |
| 22 | Deep Blue Sea | Renny Harlin | $60 million | $165 million | 2.75x | |
| 23 | Eyes Wide Shut | Stanley Kubrick | $65 million | $162.1 million | 2.49x | |
| 24 | Payback | Brian Helgeland | $50 million | $161.6 million | 3.23x | |
| 25 | The Bone Collector | Phillip Noyce | $48 million | $151.5 million | 3.16x | |
| 26 | The General's Daughter | Simon West | $95 million | $150 million | 1.58x | |
| 27 | Inspector Gadget | David Kellogg | $75 million | $134 million | 1.79x | |
| 28 | The Talented Mr. Ripley | Anthony Minghella | $40 million | $128.8 million | 3.22x | |
| 29 | The Thomas Crown Affair | John McTiernan | $48 million | $125.3 million | 2.61x | |
| 30 | Message in a Bottle | Luis Mandoki | $30 million | $118 million | 3.93x | |
| 31 | Blue Streak | Les Mayfield | $65 million | $117.7 million | 1.81x | |
| 32 | Anna and the King | Andy Tennant | $92 million | $114 million | 1.24x | |
| 33 | Three Kings | David O. Russell | $48 million | $107.7 million | 2.24x | |
| 34 | She's All That | Robert Iscove | $10 million | $103.2 million | 10.32x | |
| 35 | Fight Club | David Fincher | $63 million | $102 million | 1.62x | |
| 36 | Any Given Sunday | Oliver Stone | $55 million | $100.2 million | 1.82x | |
| 37 | Bowfinger | Frank Oz | $55 million | $98.6 million | 1.79x | |
| 38 | 8mm | Joel Schumacher | $40 million | $96.6 million | 2.42x | |
| 39 | Forces of Nature | Bronwen Hughes | $75 million | $93.9 million | 1.25x | |
| 40 | Deuce Bigalow: Male Gigolo | Mike Mitchell | $17 million | $92.9 million | 5.46x | |
| 41 | Galaxy Quest | Dean Parisot | $45 million | $90.7 million | 2.02x | |
| 42 | Stigmata | Rupert Wainwright | $29 million | $89.4 million | 3.08x | |
| 43 | The Cider House Rules | Lasse Hallström | $24 million | $88.5 million | 3.69x | |
| 44 | Bicentennial Man | Chris Columbus | $100 million | $87.4 million | 0.87x | |
| 45 | Never Been Kissed | Raja Gosnell | $25 million | $84.6 million | 3.38x | |
| 46 | South Park: Bigger, Longer & Uncut | Trey Parker | $21 million | $83.1 million | 3.96x | |
| 47 | Cruel Intentions | Roger Kumble | $10.5 million | $75.9 million | 7.23x | |
| 48 | Random Hearts | Sydney Pollack | $64 million | $74.6 million | 1.17x | |
| 49 | The Hurricane | Norman Jewison | $50 million | $74 million | 1.48x | |
| 50 | Life | Ted Demme | $80 million | $73.4 million | 0.92x | |
| 51 | All About My Mother | Pedro Almodóvar | $600 million | $68 million | 0.11x | |
| 52 | The Messenger: The Story of Joan of Arc | Luc Besson | $85 million | $67 million | 0.79x | |
| 53 | House on Haunted Hill | William Malone | $37 million | $65 million | 1.76x | |
| 54 | The 13th Warrior | John McTiernan | $85 million | $61.7 million | 0.73x | |
| 55 | The Insider | Michael Mann | $90 million | $60.3 million | 0.67x | |
| 56 | The Story of Us | Rob Reiner | $50 million | $58.9 million | 1.18x | |
| 57 | The Ninth Gate | Roman Polanski | $38 million | $58.4 million | 1.54x | |
| 58 | Lake Placid | Steve Miner | $35 million | $56.9 million | 1.63x | |
| 59 | Mickey Blue Eyes | Kelly Makin | $36 million | $54.3 million | 1.51x | |
| 59 | Varsity Blues | Brian Robbins | $16 million | $54.3 million | 3.39x | |
| 61 | 10 Things I Hate About You | Gil Junger | $13 million | $53.5 million | 4.12x | |
| 62 | Magnolia | Paul Thomas Anderson | $37 million | $48.4 million | 1.31x | |
| 63 | Girl, Interrupted | James Mangold | $24 million | $48.3 million | 2.01x | |
| 64 | Man on the Moon | Miloš Forman | $52 million | $47 million | 0.90x | |
| 65 | For Love of the Game | Sam Raimi | $50 million | $46.1 million | 0.92x | |
| 66 | Tea with Mussolini | Franco Zeffirelli | $12 million | $45.5 million | 3.79x | |
| 67 | Dogma | Kevin Smith | $10 million | $45 million | 4.50x | |
| 68 | Arlington Road | Mark Pellington | $31 million | $41.1 million | 1.33x | |
| 69 | Blast from the Past | Hugh Wilson | $35 million | $40.3 million | 1.15x | |
| 70 | Angela's Ashes | Alan Parker | $50 million | $37.3 million | 0.75x | |
| 71 | The Bachelor | Gary Sinyor | $21 million | $36.9 million | 1.76x | |
| 72 | My Favorite Martian | Donald Petrie | $65 million | $36.8 million | 0.57x | |
| 73 | Baby Genius | Bob Clark | $12 million | $36.5 million | 3.04x | |
| 74 | EDtv | Ron Howard | $80 million | $35.2 million | 0.44x | |
| 75 | October Sky | Joe Johnston | $25 million | $34.7 million | 1.39x | |
| 76 | The Best Man | Malcolm D. Lee | $9 million | $34.5 million | 3.83x | |
| 77 | Instinct | Jon Turteltaub | $60 million | $34.1 million | 0.57x | |
| 78 | Mystery Men | Kinka Usher | $68 million | $33.5 million | 0.49x | |
| 79 | The Iron Giant | Brad Bird | $70 million | $31.7 million | 0.45x | |
| 80 | Virus | John Bruno | $75 million | $30.7 million | 0.41x | |
| 81 | Superstar | Bruce McCulloch | $14 million | $30.6 million | 2.19x | |
| 82 | East Is East | Damien O'Donnell | £1.9 million | $30.4 million | ||
| 83 | Go | Doug Liman | $20 million | $28.5 million | 1.43x | |
| 84 | The Deep End of the Ocean | Ulu Grosbard | $38 million | $28 million | 0.74x | |
| 84 | The Out-of-Towners | Sam Weisman | $40 million | $28 million | 0.70x | |
| 86 | The Other Sister | Garry Marshall | $35 million | $27.8 million | 0.79x | |
| 87 | The Wood | Rick Famuyiwa | $6 million | $25 million | 4.17x | |
| 88 | The Corruptor | James Foley | $25 million | $24.5 million | 0.98x | |
| 89 | Anywhere but Here | Wayne Wang | $23 million | $23.6 million | 1.03x | |
| 90 | Being John Malkovich | Spike Jonze | $13 million | $23.1 million | 1.78x | |
| 90 | Stir of Echoes | David Koepp | $12 million | $23.1 million | 1.93x | |
| 92 | Snow Falling on Cedars | Scott Hicks | $35 million | $23 million | 0.66x | |
| 93 | Buena Vista Social Club | Wim Wenders | $23 million | |||
| 94 | Drive Me Crazy | John Schultz | $8.5 million | $22.6 million | 2.66x | |
| 95 | At First Sight | Irwin Winkler | $40 million | $22.4 million | 0.56x | |
| 96 | Muppets from Space | Tim Hill | $24 million | $22.3 million | 0.93x | |
| 97 | Boys Don't Cry | Olaf Lubaszenko | $2 million | $20.7 million | 10.35x | |
| 98 | The Astronaut's Wife | Rand Ravich | $34 million | $19.6 million | 0.58x | |
| 99 | Summer of Sam | Spike Lee | $22 million | $19.3 million | 0.88x | |
| 100 | The Thirteenth Floor | Josef Rusnak | $16 million | $18.5 million | 1.16x |
Figures are shown in the currency they were reported in (Wikipedia, Wikidata or TMDB); no conversion.