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The highly anticipated superhero film Deadpool & Wolverine was released last weekend (July 26th). Between the eye-popping action scenes, hilarious interactions between characters and the unforgettable cameos, many people are already considering the movie a classic, which got us to thinking. We put together a gallery of classic films that were released in 1999 and turn or have already turned 25 this year. Click inside to take a trip down memory lane!

The year 2023 was a huge one when it came to movies and the box-office. As fans, we saw not one but two movies, Barbie and The Super Mario Bros. Movie, both gross over 1 billion dollars. In addition to those two, there was a bevvy of films that captivated audiences worldwide. Oppenheimer (which was released on the same day as Barbie) was a smash that left people in complete awe. We were blessed to see new installments added to franchises that we have grown to love with the releases of Guardians of the Galaxy Vol. 3, Fast X, Spider-Man: Across the Spider-Verse and Mission: Impossible – Dead Reckoning Part One. Wonka, The Little Mermaid and even The Color Purple gave us a blast from the past as remakes of classic films. Down the line, when we look back at the year, it will definitely stand out as a great one.

Another year that we can say the same thing about is 1999. There is a host of bonafide classics that made their way onto our screens. The fourth film of the groundbreaking Star Wars series was released and blew every other film out of the water numbers wise. Two of the world’s favorite animated characters, Woody and Buzz Lightyear, got a sequel. Thanks to Laurence Fishburne, Keanu Reeves, Brad Pitt and Edward Norton, action movies were in high demand. Funny men like Martin Lawrence, Eddie Murphy, Jim Carrey, Rob Schneider, Michael Myers and Adam Sandler continued to solidify themselves as household names with films that still make us cry of laughter to this day. Fantasy films and psychological thrillers left their mark also as The Green Mile and The Sixth Sense showed there is always a new boundary you can push in the film world. No matter what your cup of tea is, in 1999 there was something for you. To celebrate these films’ legacies, we put together a gallery of films that are turning 25 this year. Let us know your favorites and if we missed any in the coments!

1. The Wood


Source:Rotten Tomatoes Classic Trailers

2. The Green Mile


Source:Rotten Tomatoes Classic Trailers

3. Life


Source:Rotten Tomatoes Classic Trailers

4. The Matrix


Source:Rotten Tomatoes Classic Trailers

5. The Mummy


Source:Rotten Tomatoes Classic Trailers

6. Blue Streak


Source:Rotten Tomatoes Classic Trailers

7. Toy Story 2


Source:Rotten Tomatoes Classic Trailers

8. Any Given Sunday


Source:Rotten Tomatoes Classic Trailers

9. American Pie


Source:Movieclips

10. Fight Club


Source:Rotten Tomatoes Classic Trailers

11. The Sixth Sense


Source:Rotten Tomatoes Classic Trailers

12. Tarzan


Source:Rotten Tomatoes Classic Trailers

13. Stuart Little


Source:Rotten Tomatoes Classic Trailers

14. Star Wars Episode 1: The Phantom Menace


Source:Star Wars

15. Big Daddy


Source:Rotten Tomatoes Classic Trailers

16. Wild Wild West


Source:Rotten Tomatoes Classic Trailers

17. In Too Deep


Source:The Baltimore Movie Trailer Park

18. American Beauty


Source:Rotten Tomatoes Classic Trailers

19. Runaway Bride


Source:Rotten Tomatoes Classic Trailers

20. Trippin’


Source:Black Film History

21. The Blair Witch Project


Source:Rotten Tomatoes Classic Trailers

22. Cruel Intentions


Source:Sony Pictures Entertainment

23. The Talented Mr. Ripley


Source:Rotten Tomatoes Classic Trailers

24. Man On The Moon


Source:Rotten Tomatoes Classic Trailers

25. Deuce Bigalow Male Gigolo


Source:Eddie Griffin

26. South Park: Bigger, Longer & Uncut


Source:666satan665

27. Office Space


Source:Rotten Tomatoes Classic Trailers

28. 10 Things I Hate About You


Source:Rotten Tomatoes Classic Trailers

29. Austin Powers: The Spy Who Shagged Me


Source:Rotten Tomatoes Classic Trailers

30. Three Kings


Source:Warner Bros.