10 Best Ryan Reynolds Movies, Ranked

Ryan Reynolds has been in several movies over the years, and he has split his time between box office blockbusters and genre films that have become cult favorites. Reynolds got his big break on television, first in the teenage soap opera Hillside and then later in the sitcom Two Guys and a Girl, which also starred Nathan Fillion. There were smaller TV shows and some random movies, but things changed in 2002.

That was the year Reynolds starred in National Lampoon's Van Wilder. His charisma and comedic chops allowed him to skyrocket into leading man territory, and he started landing more cameo and supporting roles, often stealing the show. The exposure let him gain work across genres, including comic book movies, rom-coms, and horror releases.

Reynolds will star in a new movie in 2026 called Mayday, a buddy comedy with Kenneth Branagh on Apple TV, and while its legacy remains to be seen, it just proves that the actor is always working and delivering big performances. With Reynolds continuing his role as Deadpool in the Marvel Cinematic Universe and always popping up in different projects, his career remains among the most successful in Hollywood today.

10 Van Wilder (2002)

While Reynolds made his name on TV, he enjoyed his big-screen breakout role one year after Two Guys and a Girl ended. This is Van Wilder, a movie that is part of National Lampoon's movie legacy. As expected from a company like National Lampoon, this is an R-rated sex comedy that stars Reynolds as the title character, a seventh-year college student who is having too much fun to graduate.

Kal Penn also enjoyed his breakout in this movie as exchange student Taj, who ends up negatively influenced by Wilder's lack of care about anything but partying. The movie was made for $5 million and was a huge success, making $38.3 million worldwide. The reviews were poor, but that was expected from the genre. It has since become a cult classic and is a big reason for Reynolds' success.

9 Waiting… (2005)

Released in 2005, Waiting... is a comedy movie that stars Justin Long as Dean, an employee at a restaurant named Shenaniganz. When his mother lets him know someone from his school has gotten a high-paying job, Dean starts to question his life decisions. Reynolds stars as Monty, Dean's co-worker and friend, someone who has no problem with the fact that he works at the restaurant.

While Reynolds is not the star here, he plays a big role in the movie and is even featured in most of the promotional materials for the film. Thanks to the low $3 million budget, it was a success, making $18.6 million at the box office. It has since become a cult classic and is a movie beloved by people who worked in the restaurant industry, as it is similar to Clerks in showing the stress of working this particular job.

8 The Proposal (2009)

In 2009, Reynolds starred in a high-profile rom-com opposite Sandra Bullock. The movie is The Proposal, with Bullock starring as a book editor named Margaret who faces being deported back to Canada. She convinces her assistant, Andrew, to enter into a fake relationship so she can find a way to stay in the United States. The story is problematic in the boss-employee dynamic, but that didn't stop its success.

The Proposal made $317 million, making it one of the highest-grossing rom-coms of Bullock's career. Critics were not impressed, but the box office success proves that this is a movie that fits into the genre perfectly, with much of the praise going to Bullock's and Reynolds' chemistry. The movie also features a career revival for Betty White.

7 Deadpool & Wolverine (2024)

Released in 2024, Deadpool & Wolverine remains one of the most beloved Marvel Cinematic Universe movies in recent years. That all comes down to the return of Hugh Jackman as Wolverine, the return of several characters from Fox X-Men movies, and Reynolds' success at convincing Marvel to keep his franchise R-rated. It also has a fun story with multiverse escapades and the great Cassandra Nova as the villain.

It was not reviewed as well as other Deadpool movies, but that didn't hurt it at all. Despite a 77% Rotten Tomatoes score, it still broke $1.3 billion worldwide and was the highest-grossing R-rated movie of all time until The Odyssey broke that record. Thanks to the box office totals, Deadpool & Wolverine remains one of Reynolds' best movies, regardless of critical reviews.

6 Definitely, Maybe (2008)

In 2008, Reynolds starred in what might go down as his best romantic comedy, and that is because it is completely unlike anything else in the genre. In Definitely, Maybe, Reynolds stars as Will Hayes, a soon-to-be-divorced father who tells his young daughter (Abigail Breslin) the story of three of his past great loves. He changes all their names, so his daughter has to guess which of the women is her mother.

The cast is amazing, with Isla Fisher, Rachel Weisz, and Elizabeth Banks playing the three past romances at the center of this mystery. This is a male-driven rom-com, which is different, and the main relationship is between a father and his daughter, which also helps differentiate it. This might be the best romance genre movie in Reynolds' entire career, showing him as more than a cocky wisecracker.

5 Free Guy (2021)

In 2021, Reynolds starred in a massive blockbuster with Shawn Levy called Free Guy. This is Levy and Reynolds' first movie together before Levy joined the Deadpool franchise. The film is a movie that takes place inside a video game, where Reynolds plays Guy, someone who is a non-playable character who gains sentience and realizes he is in an open-world video game, and then he sets out to find his freedom.

The film was a monster success, making $331.5 million worldwide as one of the biggest post-COVID movie releases. It was better than most movies based on actual video games, and it includes some great moments, including Chris Evans' cameo as himself in a Captain America joke and Channing Tatum in a hilarious supporting role as a superfan avatar.

4 Adventureland (2009)

In 2009, Reynolds starred in the indie coming-of-age movie Adventureland, directed by Greg Mottola (Superbad). In this film, Reynolds plays Mike Connell, the maintenance man at a local run-down amusement park in 1987. The film follows the kids and college students who work there on break, as they attempt to figure out their lives. Reynolds delivers an interesting change from his normal wisecracking character here.

Instead, he is the cool guy, a mentor to many of the young adults working there. However, there is also a twist in the movie where he proves he is not really who he pretends to be at work, and it makes the story even more powerful. Kristen Stewart delivers a solid performance, helping separate her from her Twilight days, and Jesse Eisenberg is the actual main character in the story.

3 Mississippi Grind (2015)

Released in 2015, Mississippi Grind is one of Reynolds' least-known movies, but it also stands out as one of his best. Despite its lack of public acknowledgment, it has a 91% Rotten Tomatoes score, which makes it the best-reviewed movie of Reynolds' entire career. Reynolds plays Curtis, a charismatic drifter and gambler who becomes friends with a down-on-his-luck gambler, Gerry, played by Ben Mendelsohn.

The two are on the way to a high-stakes poker game in New Orleans, and this allows Reynolds and Mendelsohn to carry the load with great dialogue and performances in a comedy-drama from director Anna Boden and Ryan Fleck, who also directed Marvel's Captain Marvel. The A24 movie was a flop, not even making $500,000 at the box office, despite its fantastic reviews.

2 Buried (2010)

Buried is not only one of Ryan Reynolds' best movies of his career, but it is also the most intense movie he has ever appeared in. This is a 2010 psychological thriller by Rodrigo Cortés, and the entire 95 minutes of the movie takes place inside a coffin with Reynolds as the only actor on screen. Reynolds plays Paul Conroy, an American truck driver in Iraq who is abducted and buried alive.

Buried shows Paul in the coffin with only a cellphone, with a limited battery, a pen, and a Zippo lighter. The movie was made on a low budget of around $2 to $3 million and made $21.3 million worldwide. It has an 87% Rotten Tomatoes score and is widely considered Reynolds' best non-comedic performance.

1 Deadpool (2016)

Deadpool is a movie that Reynolds fought to get made after he starred as Wade Wilson in X-Men Origins: Wolverine, a film that ruined the character. Reynolds even admitted to releasing leaks of the screen tests online to get fans excited and to push Fox into finally greenlighting the project. Reynolds got to star as Deadpool in an R-rated movie, which was unusual for a major superhero movie at the time.

What resulted was a record-breaking opening, with Deadpool becoming the first R-rated movie to break $100 million domestically in its opening weekend, and its $783 million worldwide was the highest for any R-rated movie at the time. This record held until another comic book movie, Joker, beat it in 2019. Deadpool also has an 85% Rotten Tomatoes score, giving Ryan Reynolds a great critical and box office success.