Among the greatest comedic performers of the 21st century standsRyan Reynolds, who’s starred or at least appeared in dozens of hilarious films since debuting in the 1990s. One role in particular likely materialized in your head off the bat. But Reynolds has plenty of other famous roles under his belt that fit the comedic mold. Not just the Merc with a Mouth.
You should without a doubt recognize most of the titles that appear herein, if you haven’t seen them outright. But many films may appear more unfamiliar. Still, they’ll make you laugh along the way, Here are Ryan Reynolds' 20 funniest movies, ranked.
20Mississippi Grind
Co-starring Ben Mendelsohn, this is among the more subtle films on the list with regard to overall humor. That’s mostly why it kicks things off. If this were ranking Ryan Reynolds movies by their outright caliber,Mississippi Grind(2015) would likely land much higher. It was well received upon release, holding a whopping 91% approval rating on critical consensus website Rotten Tomatoes.
But it came up remarkably short at the worldwide box office, and it’s by no means held in high regard today. It’s easily among the most undervalued films everdistributed by A24. For those unfamiliar: Its plot follows Mendelsohn’s protagonist Gerry, a down-on-his-luck gambler who’s taken under the wing of Curtis (played by Reynolds), an up-and-coming poker player with palpable poise. And although this isn’t the most laugh-out-loud films on the list, many behind-the-scenes efforts work in great comedic tandem with the performers to landMississippi Grindat the start of the list.
19Definitely, Maybe
Off the bat, it’s worth noting that this entry boasts one of the most star-studded casts on the list: aside from Reynolds, there’s also Isla Fisher and Rachel Weisz, along with Elizabeth Banks, Derek Luke, Abigail Breslin, and Kevin Kline. That star power speaks for itself, as those actors propel any project they’re in to new heights. Well, given the proper direction. And in this case, director Adam Brooks also penned the script.
Considering how well the project was seen into fruition by the aforementioned performers, Brooks was undoubtedly the man for the job. The first of three romantic comedies to be featured on the list,Definitely, Maybe(2008) resonated well with fans and critics alike. Reynolds plays protagonist Will Hayes who helps his daughter come to terms with her parents getting divorced by detailing his past romantic relationships. That includes her mother, played by Banks, and each performer plays a part in landingDefinitely, Maybeat number 19.
186 Underground
This is among the funniestentries in Michael Bay’s filmography, though that’s not saying much. He’s of course known for his action stints likeArmageddon(1998) andTransformers(2007). And even his more comedic films boast plenty of well-shot and engaging sequences of stunts: takeBad Boys(1995), for example. The film at hand isn’t quite as comically valuable, but it will nonetheless make you laugh all throughout its action-packed plot.
Here in6 Underground(2019), a star-studded cast is led by Reynolds as six vigilantes execute a coup d’état against a Turgistan dictator. Each character is the best at what they do, from contract killing to getaway driving. And while their respective performers by no means put forth performances worthy of particular praise, they all show up in valiant enough fashion to land6 Undergrounda spot on the list.
17Spirited
The most recent film on the list isSpirited(2022), a Christmas comedy co-starring Will Ferrell. A modern retelling ofA Christmas Carol— written by Charles Dickens in 1843 — this is among the funnier adaptations in a long line thereof.The Muppet Christmas Carol(1992) is up there, whileScrooged(1988) with Bill Murray most likely takes the comedic cake. ButSpiritedis a valiant effort nonetheless, and that’s primarily by dint of its two leads.
Ryan Reynolds and Will Ferrell are among the foremost comedic minds of their generations, with the latter starring as Ebeneezer Scrooge. The actor at hand appears as a media consultant named Clint Briggs, with Octavia Spencerin a supporting roleas Kimberly. And althoughSpiritedis still new compared to almost every other entry on the list, it still deserves a spot among their ranks.
16The Hitman’s Bodyguard
Some of the best rapport from any film on the list is shared between Reynolds and Samuel L. Jackson here inThe Hitman’s Bodyguard(2017). It’s one of many films on the list that’s held in higher regard with fans than it is with critics, and that showed in the money it accrued at the worldwide box office: $184 million off a budget between $30-70 million. That’s exactly how a sequel was spawned:Hitman’s Wife’s Bodyguard(2021).
And as contrived as that name may appear, its plot is somehow worse. It’s best you stick to the original — it’s worth noting, though, that if you do indulge in either, you should go in expecting to laugh. Not much else. The leads in Reynolds and Jackson share a back-and-forth showcasing of hilarious banter that highlights the film until its final frame. Even if it’s hardly one of his best movies,The Hitman’s Bodyguardshould be remembered as one of the funniest films from Ryan Reynolds.
15Just Friends
Co-starring Amy Smart and Anna Faris, this entry follows Ryan’s protagonist Chris Brander,an overweight high school student. He’s in love with his best friend, Jamie (played by Smart), while Faris shows up as his girlfriend ten years down the road. Chris has shaved off the weight and now works as a high-profile executive for a record label. From there, he returns to his hometown and attempts again to win Jamie’s heart.
Pretty straightforward. But the comedy materializes in the performances of its three leads. Though not the best film you’ll read about today, it’s still a hilarious and iconic entry among Reynolds' filmography. But it’s also worth noting for marking the first film on the list to feature Anna Faris. She’s among the most famous Reynolds collaborator ever, and she without a doubt helps landJust Friendsat number 11.
14The Proposal
A surprising delight in terms of comedic value,The Proposal(2009) should go down as one ofthe funniest romantic comediesto hit the silver screen over the past few decades. And most of its humor can be attributed to the performances of its leads: not just Ryan Reynolds, but also Sandra Bullock. This is arguably the latter’s funniest effort to date as she plays a book editor named Margaret Tate.
Related:Best Sandra Bullock Movies, Ranked
Reynolds shows up as her assistant, Andrew Paxton, whom she recruits to marry her in order to avoid being deported back to Canada. These are two of the most famous actors of their generation, and they share a hilarious rapport around every corner of the film’s plot. AlthoughThe Proposalfailed to resonate to any notable degree with critics, audiences were right to attend their local movie theaters. This is the best rom-com of Ryan’s career.
13Paper Man
InPaper Man(2009), well-known actorJeff Bridges appearsas Richard Dunn, a writer who relies on an imaginary friend from his childhood to help him make life decisions. That’s where Reynolds comes in. He portrays the made-up character Captain Excellence, while another famous name in Lisa Kudrow also shows up — she plays Richard’s wife, named Claire.
ButPaper Manis notable not just for its comedic value, but also for the appearance from Emma Stone. This marks her first of several appearances on the list, with Stone going down as one of the most frequent collaborators that Reynolds has to offer. And whilePaper Manis far from the greatest film they’ve worked on together, it’s undoubtedly a funny one.
12Adventureland
This entry co-stars Jesse Eisenberg and Kristen Stewart, with a star-studded supporting cast: Bill Hader, Kristen Wiig, and Martin Starr. But even among all those comedic minds, there’s a solid argument that Reynolds steals the show (okay, Hader does, but it’s close). When he commits himself to a character, he shines as perhaps the funniest facet of every film he’s in, even if he plays kind of a scumbag, as he does here.
Here inAdventureland(2009), he works (along with the rest of the characters) at the titular run-down amusement park. And each thespian shares a brilliant, hilarious dynamic until the film’s final, funny frame. There’s a fair bit of poignance, but at the end of the day,Adventurelandis easily among the most uproarious movies from Ryan Reynolds.
11Waiting…
Co-starring Anna Faris and Justin Long as fellow members of the waitstaff, this is another ofthe most famous comediesfrom Ryan’s career followingVan Wilderon the list. On any given day,Waiting…(2005) could place even higher on the list. Its jokes aren’t exactly intelligent, but they’re silly and well-performed enough to lead the comedy project at hand to new heights.
On top of the aforementioned performers, famous names like Luis Guzmán and Dane Cook can be found preparing the food from the chaotic confines of the kitchen. Meanwhile, David Koechner appears as the manager, Dan. They all perform to hilarious extents, with the cast ofWaitinglanding the project as a whole here at number 11.
