No.10 Definitely, Maybe (2008)
Ryan Reynolds plays a father who tells his ten-year-old daughter (Abigail Breslin) the tales of his previous romantic experiences, including how he ended up marrying her mother, to help explain his imminent divorce in a rom-com that resembles CBS’ How I Met Your Mother just a little bit. This picture is a delightful, intelligent romantic dramedy with Isla Fisher, Rachel Weisz, and Elizabeth Banks as well.
No.9 Adventureland (2009)
Adventureland is a comedy about summertime park employees in 1987 that was written and directed by Greg Mottola of Superbad and is partially based on the theme park in upstate New York. Reynolds plays the senior maintenance worker for the Fun Zone, which is a supporting role, but it’s still a fantastic way to use him in the ensemble (while also nodding to his past “big fish in a little pond” performances he’d had in Waiting and Van Wilder). Along with Reynolds, Kristen Wiig, Bill Hader, and Martin Starr, Jesse Eisenberg and Kristen Stewart play the lead roles.
No.8 The Proposal (2009)
2009’s The Proposal from Anne Fletcher of Step Up and 27 Dresses was like a charisma eruption. In this romantic comedy, which starred Reynolds and Sandra Bullock, a female executive convinces her assistant to pose as her fiancé in order to prevent being deported to Canada. Here, Reynolds and Bullocks had incredible chemistry since they both had perfect comedic timing and had the unique ability to play off one another. Malin Akerman, Craig T. Nelson, Mary Steenburgen, and Betty White are also featured.
No.7 Buried (2010)
Tight-lipped thriller Another bold departure for Reynolds was Buried from 2010. But it worked, using very little to release a great deal of tension. Kidnapped as an American truck driver in Iraq, he was left with just a lighter, flask, flashlight, knife, glow-sticks, pen, pencil, and a cell phone before being buried alive in a coffin. Reynolds gave a frenzied, tense performance as a man fighting for his life in this current crucible.
No.6 Deadpool 2 (2018)
No.5 Free Guy (2021)
Ryan Reynolds gave a riotously entertaining performance as an NPC in a GTA-style MMO who gets sentience and falls in love with a real-world player character in Free Guy, which debuted after many catastrophic delays to a strong box office take. Free Guy demonstrated that Reynolds could create an original character that could produce a great hit thanks to a catchy concept and pleasant, self-aware humor. Along with Taika Waititi, Jodie Comer, Lil Rel Howery, Utkarsh Ambudkar, Joe Keery, and others star.
No.4 Pokemon Detective Pikachu (2019)
In the 2019 action-mystery Pokemon Detective Pikachu, Ryan Reynolds provided Detective Pikachu with his warm whimsy. Detective Pikachu, which also starred Justice Smith, Kathryn Newton, Ken Watanabe, and Bill Nighy, was a rare treat among video game movies, largely because of Ryan Reynolds’ appeal (and facial-motion capture) as the coffee-obsessed detective. Reynolds gave an endearingly comedic performance that was more in line with his subversive Deadpool schtick than you might anticipate from a Pokemon movie.
No.3 The Adam Project (2022)
With Netflix’s The Adam Project, Stranger Things and Free Guy director Shawn Levy scored a sleek, futuristic family adventure that perfectly encapsulated the vibe of ’80s sci-fi. Reynolds portrays a dystopian future pilot who goes back in time to find out what happened to his wife but ends himself in the wrong year and encounters his younger 12-year-old self (Walker Scobell). The Adam Project, which also stars Mark Ruffalo, Jennifer Garner, and Zoe Saldaa, is a clever mash-up of movies like Back to the Future, The Last Starfighter, and others. See more like this in our list of the top science fiction films on Netflix.
No.2 Mississippi Grind (2015)
Reynolds and Ben Mendelsohn star in Mississippi Grind, one of the lesser-known movies on this list, from the (ultimate) Captain Marvel directors Anna Boden and Ryan Fleck. It’s a drama about a gambler on the road to a high-stakes poker game in New Orleans who believes his new friend (Reynolds) is a good-luck charm. Reynolds and Mendelsohn collaborate to produce a tragicomic character study that will live on forever.
No.1 Deadpool (2016)
Ryan Reynolds has at last discovered the part for which he was made. Reynolds first portrayed mercenary Wade Wilson in 2009’s X-Men Origins: Wolverine, and the casting of Reynolds as Deadpool was terribly teased at the time (who was robbed of his ability to speak and snark in the third act). However, Tim Miller’s Deadpool did everything right, instantly demonstrating the excellence of this actor/IP pairing. A comedy-action triumph, Deadpool had hilarious one-liners, stylish action, and tons of enjoyable fan service.
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