3. 90s Movie There's Something About Mary (1998)

Arguably one of the best RomComs from the 90s, There’s Something About Mary was made by the talented minds who created Dumb & Dumber. Furthermore, the movie remains one of the greatest works of Cameron Diaz. Likewise, Matt Dillon and Ben Stiller starred alongside Diaz in the movie.

There's Something About Mary movie poster
There’s Something About Mary movie poster.
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The movie was a massive success in both commercials and with the critics. Furthermore, There’s Something About Mary managed to win a plethora of awards. The crowning jewel would be MTV’s award for the Best Movie. Additionally, the movie managed to collect over $369 million at the box office worldwide.

2. Propelling Brad Pitt to Maga Stardom Fight Club (1999)

Fight Club remains one of the top pop-culture icons. Moreover, the movie quote “What are the two rules of Fight Club” has been cemented its slot in movie history. Moreover, the movie held an amazingly talented cast of Brad Pitt, Helena Bonham Carter, Jared Leto, and more.

Brad Pitt in the movie Fight Club
Brad Pitt in the movie Fight Club.
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The Oscar-nominated movie managed to gain a massive following. Furthermore, the movie managed to collect millions at the box office. More on the earnings, Fight Club grossed over $101 million at the global box office.