Paul Ruddwasn’t always known as the quirky superhero Ant-Man. Indeed, the actor made his debut back in 1992 with the television dramaSisters, after graduating from the University of Kansas where he majored in theater. In the 30 years of his career, he has starred in multiple movies and TV series, was named as part of theForbesCelebrity 100 in 2019 andPeople’s “Sexiest Man Alive” in 2021, and has recently joined theSNL five-timers club, having hosted thesketch comedy tv showfive different times.

During the 90s, Rudd worked tirelessly as he rose the ranks of Hollywood, appearing in many hit movies and TV series, fromCluelessto being a honorary regular inFriends. He was an actor that audiences were familiar with, but it wouldn’t be until the turn of the century that his career would skyrocket. Now, Rudd has the enviable position of playing a major role in the MCU, with his third leading movie,Ant-Man and the Wasp: Quantumaniacurrently filming and set to release in 2023. What was his career like back in the 90s? Let’s take a look at Paul Rudd’s best movies from the previous century.

Paul Rudd and Claire Danes in Romeo + Juliet

Related:Ant-Man and the Wasp: Quantumania: Everything We Know About the Cast So Far

6William Shakespeare’s Romeo and Juliet (1996)

Starting with a romantic crime tragedy,Romeo + Julietreleased back in 1996 and starred Leonardo DiCaprio and Claire Danes as the titular star-crossed lovers. It’s safe to say that everyone knows the classic William Shakespeare tragedy, telling the story of two young people who fall in love with each other despite their famines being rivals and opposing their relationship. As for Rudd, his role was pretty minimal, but he still left an impression. He played the role of Dave Paris, the governor’s son and Juliet’s fiancé. Thismodern Shakespeare adaptationgave Rudd a chance to make a small name for himself in his pre-fame years.

5200 Cigarettes (1999)

200 Cigarettesis a comedy movie set in 1981 with the plot occurring on New Year’s Eve. The story follows many different characters on the streets of New York and their journey of getting to Monica’s party. Rudd plays the character of Kevin, Lucy’s best friend, a duo with a lot of unresolved sexual tension. Perhaps it’s because of the negative reviews the movie received, but the movie stays unstreamable; you can either buy it on Blu-Ray or break the rules. The audience tends to have a love-hate relationship with the film, considering how it has a pretty great cast and had a set of decent moments, but also isn’t the best movie you’ll ever watch.

4The Cider House Rules (1999)

Having an ensemble cast of Tobey Maguire, Charlize Theron, Michael Caine, and Paul Rudd,The Cider House Rulesis a drama movie based on a book of the same name written by John Irving, who also wrote the entirety of the screenplay. Set in the World War II era, the plot follows Homer (Maguire) who lives in an orphanage with a doctor who trained him. The movie accompanies Homer on his journey of leaving the orphanage. As for Rudd, he plays the character of Lt. Wally Worthington, a volunteer pilot in the army while his wife cheats on him with Homer.

Related:Paul Rudd: The Man Who Can’t Age and His Best Movies

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3Overnight Delivery (1996)

Reese Witherspoon and Paul Rudd star together in a romantic road movie as a college student and a stripper, who travel across America to get rid of a falsely delivered package to Rudd’s girlfriend. By getting released straight to video, the movie did not receive as much attention as it deserved. The overall humor-filled atmosphere and the occasional romantic scenes give the audience small bits from every area. Some of its plot aspects are so bad that they somehow turn out incredible.Overnight Deliveryis arguably one of the most underrated 90s romantic comedies.

2The Object Of My Affection (1998)

Starring Jennifer Aniston and Paul Rudd in the main roles,The Object Of My Affectionis a romantic drama which tells the story of two best friends, Nina and George. Although George (Rudd) is a gay male, pregnant Nina ends up catching feelings for him after he agrees to raise her child with her. The plot is entangled in many complications as George clearly sees Nina only as a best friend, while she struggles to hide her unwanted feelings for him. It’s up to you to decide whether the movie serves as a good example of LGBTQ+ representation or not. No matter the answer, the movie is indeed a heart-warming watch.

1Clueless (1995)

Last but not least, the cult followingCluelesssaw Paul Rudd starring as Josh, the main character Cher’s ex-stepbrother. The plot mainly focuses on Cher and her attempts at giving one of the new girls a makeover as a good deed. This eventually backfires on her, as she starts becoming more and more popular than Cher and decides to pursue her feelings for Josh. All this leads to a big realization that all this time she was actually the one who had feelings for Josh. In addition to being Rudd’s stepping stone in his acting career, it’s also impossible to ignore that Rudd at 52 now looks identical to 1995 Rudd. Maybe that’s why he’s earned himself a nickname of an actor that never ages.

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