Ryan Reynolds has remained one of Hollywood’s most popular actors for nearly 20 years. He’s developed a likable public persona, become a master marketer and entrepreneur, made close friends with the kind of Hollywood talent many people would sell a necessary organ for — and he’s married to Blake Lively.
Yet, that popularity often comes with the question of the quality of his filmography. And yes, it has its share of misses. But in watching every Ryan Reynolds movie from Coming Soon (2000) to IF (2004), I’ve seen things you people wouldn’t believe: Reynolds as an amnesiac god married to Melissa Mcarthy and posing as a TV writer; I watched him play a beloved school teacher with terminal cancer in an ABC family movie; I saw him switch places with Jason Bateman after peeing in a magic fountain; witnessed him as a novelist grieving the death of his mother played by Julia Roberts, all under the eye of his abusive father played by Willem Dafoe.
But I digress, because I discovered that even his not-best movies are made immensely more watchable simply by his presence. And that’s the thing when it really comes down to it. He’s not an actor who could be described as a chameleon — though he’s shown more layers across his career than he often gets credit for, and one of his best performances was in the so-so movie The Captive (2014), which was released to DirecTV. But he’s a welcome presence even at the lowest points in his filmography. And at the highest points, he’s an agile improviser and a force that will keep you on your toes. And that’s true, regardless of whether he’s gleefully decapitating villains or struggling to escape the coffin he’s been buried in underground. Ryan Reynolds is an immensely watchable actor, even if the reason why isn’t always quantifiable.
With the release of his passion project, Deadpool & Wolverine, I take a look back at his best movies and offer the ranking below.
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13. Life (2017)
I find it hard to resist a well-crafted B-movie with an all-star cast, and Daniel Espinosa’s Life certainly fits the mold. Sure, it’s a riff on Alien (1979). But it wasn’t the first and won’t be the last. Following the success of Deadpool (2016), screenwriters Paul Wernick and Rhett Reese re-teamed with Ryan Reynolds for this sci-fi horror film that sees the crew of an international space station discover a rapidly evolving lifeform on Mars, which they dub Calvin. Reynolds along with Jake Gyllenhaal, Rebecca Ferguson, Hiroyuki Sanada, Ariyon Bakare and Olga Dihovichnaya portray scientists whose study of Calvin quickly becomes a horrific, bloody situation that literally grows beyond their control.
While Reynolds was heavily featured in the marketing, his character Rory Adams meets a gruesome end early on. Despite this, the actor still leaves an impression, and his character’s death not only pulls the film into a more serious direction (the time for jokes being noticeably over in Rory’s absence), but adds a certain sense of shock value in the notion that no one, even the film’s biggest stars, are safe. Life is a good reminder that sometimes Reynolds’s smaller, supporting roles are just as, if not more, effective than the films that put him in the lead. In films like this, he serves as a bit of extra seasoning to keep things spicy.
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12. The Adam Project (2022)
Image Credit: Doane Gregory/Netflix While everyone has varying opinions about the wide array of Netflix films in terms of quality — whether they should be played theatrically and who the target audience is — The Adam Project is one of Netflix’s better original, non-award season-centric films. Shawn Levy’s second collaboration with Ryan Reynolds, following 2021’s Free Guy, further proved the two were a great match for each other’s sensibilities, balancing humor and heart. While Free Guy has a bigger canvas to play with, The Adam Project is what sold me on Levy handling Deadpool & Wolverine.
When a fighter pilot from the future, Adam Reed (Reynolds), steals a time jet and crash lands in 2022, he encounters his 12-year-old self (Walker Scobell) who is dealing with the loss of his father, Louis (Mark Ruffalo), and the growing dissonance he’s created with his mother, Ellie (Jennifer Garner). To save his wife, Laura (Zoe Saldaña), Adam must find and stop Maya Sorian (Catherine Keener) a scientist who worked alongside Louis, and in the future becomes the dictator of a dystopia. The dynamic between Reynolds and Scobell creates a fun back-and-forth, essentially becoming a buddy movie between a young and older version of the same character. As fun as that dynamic is, and the ensuing sci-fi spectacle, The Adam Project’s biggest strength is its sincerity. Despite Reynolds’ trademark brand of sarcasm and self-deprecating humor, the standout moment is when he has a conversation with his mom, who unbeknownst to her, is her future son. There’s a genuine emotional engine behind this film. And that ending? Get out the tissues.
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11. Detective Pikachu (2019)
The first thing you think of when you consider that famous yellow cutie that the Pokémon brand was built from probably isn’t Ryan Reynolds. His initial casting as Pikachu, for which he lent his voice and face via motion capture, was initially met with understandable confusion and a share of derision. But somehow, against all odds, it works. A gumshoe Pikachu with missing memories, teaming up with a failed Pokémon trainer, Tim Goodman (Justice Smith), and a cub reporter, Lucy Stevens (Kathryn Newton), to uncover a city-wide conspiracy is the kind of clever, special effects heavy take on the neo-noir that makes the film appealing for more than just Pokémon fans.
I couldn’t count the names of Pokémon characters I know on one hand, and I didn’t go into this movie as a fan. Yet, I found Rob Letterman’s film to be an engaging fantasy-mystery, and Reynolds’ performance to be a breezy and grounding element in a film entirely set in a lore-heavy fictional reality. As far as video game adaptations go, Detective Pikachu is one of the best, and it doesn’t get overly caught up in minutiae, instead allowing the cast and audience to simply focus on delivering a good time within the framework of a silly, but no less endearing, concept. And as for a bit of film trivia, before Reynolds accepted the role, Hugh Jackman was on WB’s shortlist to voice Pikachu — but he wasn’t quite ready to don the yellow just yet.
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10. Woman in Gold (2015)
Image Credit: Courtesy of Berlin International Film Festival Simon Curtis’ biographical drama is a far cry from the other films on this list. It’s a far cry from anything in Ryan Reynolds’ career. While the film’s marketing presented a sleepy drama, Woman in Gold is a true underdog story that reflects an aspect of the Holocaust and Jewish history we don’t typically see in films. Reynolds plays Randy Schoenberg, a struggling young lawyer whose mother presents him with the opportunity to help her friend, Maria Altmann (Helen Mirren), a Jewish refugee from Austria who seeks to recover Gustav Klimt’s famous painting of her aunt — Portrait of Adele Bloch-Bauer I — which resided in her house as a child before the Nazis came and stole it.
Since that time, the painting has become a tourist attraction and symbol of Austrian culture, whose government refuses to acknowledge that culture has been built on Nazi theft from Jews. Altmann and Schoenberg not only fight against the Austrian government, but manage to take Altmann’s claim to what is rightfully hers to the Supreme Court. In Woman in Gold, it’s Reynolds’ turn to play the straight man against Mirren’s disarming humor and barely suppressed rage over the life that has been stolen from her. Yet, even in playing the straight man, Reynolds shows off his emotional capacity as Schoenberg deals with his own Jewish heritage and comes to see Altmann’s plight as more than just a job, but as a means to connect with a past and legacy he felt disconnected from. Woman in Gold is an amazing story that showcases the importance of art, not simply for the sake of beauty, but what it means in terms of identity and keeping a culture that was very nearly wiped out, alive.
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9. Free Guy (2021)
Image Credit: Courtesy of Alan Markfield/20th Century Studios’ Shawn Levy and Ryan Reynolds’ first collaboration resulted in a surprise summer hit and a win for original films (even considering the film’s many references and Easter eggs to other franchise properties). Set in the world of Massive Multiplayer Online video game (MMO), Free City, Reynolds stars as Guy, a non-playable character who breaks the pattern of his programming to help game designer Millie Rusk (Jodie Comer), whose in-game character avatar Molotov Girl has captured Guy’s attention and heart. Rusk’s source code for the game she created, Life Itself, alongside her creative partner Keys (Joe Kerry), was stolen by CEO Antwan Hovachelik (Taika Waititi) to build Free City, which he plans to replace with Free City 2, effectively erasing Guy, who he’s convinced is a glitch in the system.
It’s a film tailor-made for the video game generation that has grown up with The Sims, Grand Theft Auto and Fortnite, and all the upgrades and mods that stem from playing in those worlds. While the film plays fast and loose with the comedy, and not all of it works, Reynolds is a standout as an ordinary guy with a crush on a video game avatar who is so much cooler than he is. There are some surface-level considerations of free will and the ownership of intellectual property, but at its heart, Free Guy is a high-concept, feel-good popcorn movie with two strong performances by Reynolds and Comer, dazzling special effects and the best use of Maria Carey outside of Beau is Afraid (2023).
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8. Finder’s Fee (2001)
Image Credit: Lions Gate/Courtesy Everett Collection Did you know that before he became the host of Survivor, Jeff Probst was a filmmaker? I certainly didn’t. His debut feature (of two), which he also wrote, centers on a group of friends, Tepper (Erik Palladino), Quigley (Ryan Reynolds), Fishman (Matthew Lillard) and Bolan (Dash Mihok) who get together for a weekly poker night. The rules are simple: Everyone contributes a lottery ticket to the pot, and no one checks the numbers until the game is over.
But on this particular night, the night Tepper plans to propose to his girlfriend Carla (Carly Pope), despite his financial returns, he finds a wallet on the street outside of his apartment. And inside that wallet is the winning lottery ticket for $6 million. He calls the owner of the wallet, Avery Phillips (James Earl James), who shows up to collect what’s his. But before he does, Tepper decides to keep the lotto ticket for himself. When Avery asks to stay and play a hand, while the storm rages outside, Tepper begins to grow suspicious if Avery knows what he took. The night takes a turn towards paranoia, as the friends who all have personal grievances with one another begin to chip away at each other, while a cop, Officer Campbell (Robert Forester), searches the apartment building for an escaped convict. Reynolds’ Quigly, who seems disaffected by what’s happening around him, but always watchful, ups the stakes with a hand that changes the entire scenario and brings this kettle-pot thriller to a boil. Finder’s Fee is a tense and twisty chamber drama, and while it’s become hard to track down, it’s certainly worth the effort to find and watch it.
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7. Smokin’ Aces (2006)
Image Credit: Universal Pictures/Courtesy Everett Collection Joe Carnahan’s cult action thriller weaves a violent, frenetic and downright psychotic tale of the hunt for magician-turned-wannabe gangster-turned-informant Buddy “Aces” Israel (Jeremy Piven), holed up in a hotel in Lake Tahoe with a one-million-dollar bounty on his head. Protected by FBI special agents Richard Messner (Ryan Reynolds) and Donald Carruthers (Ray Liotta), Aces awaits extraction by bail bondsman Jack Dupree (Ben Affleck) and his lawyer Rip Reed (Jason Bateman). Of course, extraction isn’t easy, as a horde of colorful assassins ranging from a trio of neo-Nazi brothers (Chris Pine, Kevin Durand, Maury Sterling), a Spanish merc (Nestor Carbonell), a Hungarian hitman and master of disguise (Tommy Flanagan), and a duo of contract killers (Alicia Keys, Taraji P. Henson) all cross paths in the effort to claim Aces’ head for mob boss Primo Sparazza (Joseph Ruskin).
Smokin’ Aces is chaotic in the best way and stuffed to the brim with a who’s who of big name and character actors. Filled with twists, reveals and unexpected deaths, Reynolds’ Messner remains the center, holding all the rest together. His efforts to remain a good cop amid all the chaos and senseless death tests the strength of the badge he carries, and he becomes increasingly bloodied, beleaguered and disassociated from the job. It’s quite remarkable that Reynolds, at this still-early point in his career, can own the screen and remain compelling despite the host of colorful personalities, wild accents and bold character choices. He’s not without humor. But his sardonic tone and constant feeling of frustration feel like a precursor to the characteristics he would take on as Deadpool.
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6. Definitely, Maybe (2008)
Image Credit: Andy Schwartz/Universal/Courtesy Everett Collection And now for something a little calmer. While recent years have seen Ryan Reynolds step away from the rom-com arena — except for the wiggle-room of Deadpool — the 2000s placed him in a sweet spot. These rom-coms ranged from the low-point of Buying the Cow (2002) to hits like The Proposal (2009), further solidifying his status as a leading man. But one of his best from this era is Adam Brooks’ unconventional rom-com, Definitely, Maybe, which is like a streamlined version of How I Met Your Mother, with far fewer detours and a satisfying ending.
Amid being served divorce papers, political consultant Will Hayes (Reynolds) is asked by his daughter, Maya (Abigail Breslin), to tell her the story of how he met her mother, in the hopes that her father will realize what made him fall in love with her in the first place and save his marriage. So, Will tells her the story of his three defining relationships, changing the women’s names, and leaving his daughter to guess which of the three — Emily (Elizabeth Banks), April (Isla Fisher) and Summer (Rachel Weisz) — is her mother. As he illuminates how these relationships evolved and defined him over two decades, he finds himself falling in love again, though not in the way his daughter expected. There’s a real sense of vulnerability to Reynolds in this movie, and he isn’t playing the wise-ass like he has in many of his other roles. He excels at playing both a father and a romantic whose personal ambitions often conflict with his heart’s. Love might be a journey, but Definitely, Maybe is certainly a trip worth taking.
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5. Just Friends (2005)
Image Credit: New Line Cinema/Photofest And on the subject of Ryan Reynolds’ rom-coms, Roger Kumble’s Just Friends (2005) is his funniest. In this Christmas-set movie, music producer Chris Brander (Reynolds) returns to his hometown for the holidays and reconnects with his teenage crush Jamie Palamino (Amy Smart), who once, very publicly, friend-zoned him. Reynolds’ acerbic humor is out in full force here, and he plays up Chris’ never-ending series of frustrations and embarrassments well. Chris struggles to win Jamie’s affection, while another former classmate, Dusty Dinkleman (Chris Klein), also vies for her heart. Chris’ plans are further complicated by the arrival of chaotic, chronically drunk pop star Samantha James (Anna Faris), who he had a previous relationship with.
As good as Reynolds is here, the real star is Farris, who is laugh-out-loud funny and steals every scene she’s in. A Samantha James spinoff feels like one of the great missed opportunities of 2000s cinema. As much laughter as there is to get out of the film, Just Friends is still a product of its time, and not all of the jokes have aged well (there’s a cringe-worthy overuse of a homophobic slur). But despite its flaw, Just Friends is a film with its heart in the right place that isn’t afraid to call out the bullshit idea of guys thinking the girl they’re interested in owe them anything, even in the face of its happy ending.
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4. Waiting… (2005)
Image Credit: Lions Gate/Courtesy Everett Collection Rob McKittrick’s cult comedy about the trials and tribulations of working in the food service industry has achieved an almost legendary status for anyone who has ever had to serve the public. It’s a DVD passed between friends. It’s the go-to reference by a co-worker after an awful day. And it was my introduction to Ryan Reynolds and his particular brand of humor.
Set during a single work shift at the restaurant Shenaniganz, Waiting… follows the hijinks and mishaps of a regular day, complete with unrequited crushes, annoying customers and all the bullshit that the employees can get into to fight off the tedium of their jobs. These are the people who spit in your food (and much worse, as the film eagerly showcases). This is the story of a lost generation who measure time only in the form of the next shift. Dean (Justin Long), an employee for four years, contemplates the assistant manager position he’s been offered while regretting his decision to drop out of college after hearing his former classmate immediately got a job right after graduation. Alongside his gross-out humor-infatuated co-worker Monty (Reynolds), Dean shows the new hire, Mitch (John Francis Daley), the ins and outs of the service industry. Meanwhile, Monty fights off the jealous affections of his two co-workers, Serena (Anna Farris) and Natasha (Vanessa Lengies).
Featuring a who’s who of comedians including David Koechner, Luis Guzman, Dane Cook and Andy Milonakis, Waiting… is an artifact of a very specific era in comedy movies, where indie filmmakers and young actors were on the rise and raked against the studio comedies of the moment. No, the film isn’t a critical darling. But it’s certainly acquired a fanbase over the years as a millennial-defining hang-out movie that accurately captures the vibe of the mid-2000s when it felt like we were just stupidly waiting for something to happen.
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3. Deadpool (2016)
Image Credit: Courtesy of Twentieth Century Fox Tim Miller’s Deadpool felt like a breath of fresh air when it hit the cinemas in 2016. After a decade-plus of noble heroes guided by strict moral compasses and impassioned speeches, Deadpool let loose with profane, self-aware anti-hero Wade Wilson (Ryan Reynolds). While it was another origin story, Deadpool mixed up the structure, inter-splicing Wilson’s past alongside his present-day hunt for the man who turned him into a monster, Ajax (Ed Skrein). While the limitations of its budget are visible, and noted by Deadpool himself, there is an almost independent sensibility to the film given that the journey to screen was largely a labor of love from Reynolds, who’d spent 12 years trying to get the film off the ground.
Not only did the film come at the perfect point in superhero cinema, where narratives were becoming larger, darker and a bit unwieldy for some audiences, but it also gave Reynolds a high-profile boost after a series of studio disappointments. Deadpool felt like the film Reynolds’s whole career had been leading him to, and his theatrical knockdowns, as well as his growth as an actor on the indie front in the early to mid-2010s, proved to be essential to his ability to deliver on a role like Deadpool, equal parts raunchy humor and heart. While not strictly a romantic comedy, Wilson’s relationship with Vanessa (Morena Baccarin) is the driving force of the movie and makes Deadpool’s actions in that effort to get back to her all the more worthwhile. Just like the pineapple olive pizza Wade Wilson orders at the beginning, Deadpool is a pleasing mixture of sweet and salty that hits the spot.
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2. Deadpool 2 (2019)
Image Credit: Courtesy Twentieth Century Fox There’s always been some audience debate between Deadpool and Deadpool 2 over which one is better. While both are triumphs and high points in Ryan Reynolds’ career for a myriad of different reasons, the edge goes to Deadpool 2. David Leitch’s film is an expression of loss and empathy. While those qualities may seem to run counter to a film in which a foul-mouthed anti-hero is dismembering people, and watching his hastily assembled X-Force get dispatched in gruesome ways, they aren’t.
Following Vanessa’s murder, Deadpool slips into a deep, self-destructive depression. The only problem is that self-destruction is pretty hard to manifest for a guy with a healing factor who can’t die. In the process of saving an abused mutant kid, Russell (Julian Dennison), Deadpool runs afoul of the time-traveling mutant Cable (Josh Brolin), who plans to kill Russell for what the kid will do in the future. Accompanied by the luck-powered mutant, Domino (Zazie Beetz), Deadpool finds a reason to live again and fashions his own legacy. It’s not the one the X-Men, represented by Colossus (Stefan Kapicic) and Negasonic Teenage Warhead (Brianna Hildebrand) envision for him, but it fits Deadpool’s complicated sense of morals, fourth-wall-breaking humor and meta-knowledge. There’s a confidence to Reynolds in Deadpool 2, one that is apparent even behind the mask, and after a few false starts in the comic book world — Blade: Trinity (2004), Green Lantern (2011) and R.I.P.D. (2013) — Deadpool feels like Reynolds securing a career legacy set to stand the test of time.
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1. Deadpool & Wolverine (2024)
Image Credit: Jay Maidment/20th Century Studios/MARVEL The third Deadpool movie pulls out all the stops, and Reynolds finally gets to play out the team-up he’s dreamed of since the beginning: Deadpool & Wolverine. After retiring from the role after Logan (2017), Hugh Jackman unsheathes the claws again, this time as a variant version of Wolverine complete with his signature yellow costume. While Shawn Levy’s film does allow the Merc with the Mouth to play around with MCU concepts, notably the TVA, the film is largely situated in the world of the first two Deadpool films, along with The Void, a multiversal dumping ground introduced in the Disney+ series Loki.
Restraint is never something you’d expect from a Deadpool film, yet Deadpool & Wolverine is largely self-contained, to the movie’s advantage, providing plenty of time for Deadpool and Wolverine to get to know each other… violently. Reynolds goes a mile a minute in this film, a hyper-active Bugs Bunny who leaves no fourth wall unbusted, no joke untold and no drop of blood unspilled. It’s as if the six-year gap between this entry and the last one left him with a plethora of pent-up energy that explodes on the screen here. And yet, Reynolds’ greatest secret weapon remains in those instances when the jokes stop and he gives us a look at the sad, broken man Wade Wilson is. A man looking for purpose. And it’s that x-factor that makes Deadpool’s team-up with Wolverine so satisfying. These are men who hurt people as a means to suffocate the hurt they feel. And only by coming together, are they allowed to heal.
Honorable Mentions: Mississippi Grind (2015), The Amityville Horror (2005), The Voices (2014), Buried (2010).
