| 1 |  | Varsity Blues(1999) | ⭐ 6.6 |
| 2 |  | She's All That(1999) | ⭐ 6.0 |
| 3 |  | Family Guy(1999) | ⭐ 8.1 |
| 4 |  | George Carlin: You Are All Diseased(1999) | ⭐ 8.4 |
| 5 |  | Rushmore(1998) | ⭐ 7.6 |
| 6 |  | Office Space(1999) | ⭐ 7.6 |
| 7 |  | 8MM(1999) | ⭐ 6.6 |
| 8 |  | Cruel Intentions(1999) | ⭐ 6.8 |
| 9 |  | Analyze This(1999) | ⭐ 6.7 |
| 10 |  | The Matrix(1999) | ⭐ 8.7 |
| 11 |  | 10 Things I Hate About You(1999) | ⭐ 7.4 |
| 12 |  | Go(1999) | ⭐ 7.2 |
| 13 |  | eXistenZ(1999) | ⭐ 6.8 |
| 14 |  | Entrapment(1999) | ⭐ 6.3 |
| 15 |  | The Mummy(1999) | ⭐ 7.1 |
| 16 |  | Star Wars: Episode I - The Phantom Menace(1999) | ⭐ 6.5 |
| 17 |  | The Man Show(1999) | ⭐ 6.6 |
| 18 |  | The General's Daughter(1999) | ⭐ 6.4 |
| 19 |  | Big Daddy(1999) | ⭐ 6.5 |
| 20 |  | South Park: Bigger, Longer & Uncut(1999) | ⭐ 7.7 |
| 21 |  | Chris Rock: Bigger & Blacker(1999) | ⭐ 8.0 |
| 22 |  | Lake Placid(1999) | ⭐ 5.8 |
| 23 |  | The Blair Witch Project(1999) | ⭐ 6.5 |
| 24 |  | The Iron Giant(1999) | ⭐ 8.1 |
| 25 |  | The Sixth Sense(1999) | ⭐ 8.2 |
| 26 |  | The 13th Warrior(1999) | ⭐ 6.6 |
| 27 |  | Stir of Echoes(1999) | ⭐ 6.9 |
| 28 |  | Mystery, Alaska(1999) | ⭐ 6.7 |
| 29 |  | American Beauty(1999) | ⭐ 8.3 |
| 30 |  | Fight Club(1999) | ⭐ 8.8 |
| 31 |  | House on Haunted Hill(1999) | ⭐ 5.6 |
| 32 |  | Following(1998) | ⭐ 7.4 |
| 33 |  | Dogma(1999) | ⭐ 7.3 |
| 34 |  | Sleepy Hollow(1999) | ⭐ 7.3 |
| 35 |  | End of Days(1999) | ⭐ 5.8 |
| 36 |  | Toy Story 2(1999) | ⭐ 7.9 |
| 37 |  | Being John Malkovich(1999) | ⭐ 7.7 |
| 38 |  | The Green Mile(1999) | ⭐ 8.6 |
| 39 |  | Deuce Bigalow: Male Gigolo(1999) | ⭐ 5.7 |
| 40 |  | Man on the Moon(1999) | ⭐ 7.4 |
| 41 |  | Liberty Heights(1999) | ⭐ 7.0 |
| 42 |  | Election(1999) | ⭐ 7.2 |
| 43 |  | Austin Powers: The Spy Who Shagged Me(1999) | ⭐ 6.7 |
| 44 |  | Run Lola Run(1998) | ⭐ 7.6 |
| 45 |  | American Pie(1999) | ⭐ 7.0 |
| 46 |  | Eyes Wide Shut(1999) | ⭐ 7.5 |
| 47 |  | Mystery Men(1999) | ⭐ 6.1 |
| 48 |  | Galaxy Quest(1999) | ⭐ 7.4 |
| 49 |  | Double Jeopardy(1999) | ⭐ 6.5 |
| 50 |  | A Midsummer Night's Dream(1999) | ⭐ 6.4 |