Among the greatest comedic performers of the 21st century stands Ryan 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.
20 Mississippi 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 ever distributed 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 land Mississippi Grind at the start of the list.
19 Definitely, 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 landing Definitely, Maybe at number 19.
18 6 Underground
This is among the funniest entries in Michael Bay's filmography, though that's not saying much. He's of course known for his action stints like Armageddon (1998) and Transformers (2007). And even his more comedic films boast plenty of well-shot and engaging sequences of stunts: take Bad 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 in 6 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 land 6 Underground a spot on the list.
17 Spirited
The most recent film on the list is Spirited (2022), a Christmas comedy co-starring Will Ferrell. A modern retelling of A 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, while Scrooged (1988) with Bill Murray most likely takes the comedic cake. But Spirited is 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 Spencer in a supporting role as Kimberly. And although Spirited is still new compared to almost every other entry on the list, it still deserves a spot among their ranks.
16 The Hitman's Bodyguard
Some of the best rapport from any film on the list is shared between Reynolds and Samuel L. Jackson here in The 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 Bodyguard should be remembered as one of the funniest films from Ryan Reynolds.
15 Just 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 land Just Friends at number 11.
14 The Proposal
A surprising delight in terms of comedic value, The Proposal (2009) should go down as one of the funniest romantic comedies to 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.
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. Although The Proposal failed 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.
13 Paper Man
In Paper Man (2009), well-known actor Jeff Bridges appears as 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.
But Paper Man is 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 while Paper Man is far from the greatest film they've worked on together, it's undoubtedly a funny one.
12 Adventureland
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 in Adventureland (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, Adventureland is easily among the most uproarious movies from Ryan Reynolds.
11 Waiting...
Co-starring Anna Faris and Justin Long as fellow members of the waitstaff, this is another of the most famous comedies from Ryan's career following Van Wilder on 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 of Waiting landing the project as a whole here at number 11.
10 National Lampoon's Van Wilder
The role that put Reynolds on the map of Hollywood comedies is National Lampoon's Van Wilder (2002). This list is replete with collaborators of the actor of the hour, with Anna Faris and Emma Stone already being touched on. But here, Reynolds appears for the first time (both in film and on this list) with fellow comedy actor Kal Penn.
Also making an appearance is Tara Reid, with everyone performing just as adequately as they should to land Van Wilder at number 10 on the list. Some fans may dispute, claiming that Van Wilder holds up better than this placement may imply (or much worse). It is among the more famous efforts from Reynolds, after all. But in the end, it's a testament to his comedic prowess that so many other films can be deemed funnier.
9 The Voices
A horror comedy film with an emphasis on the laughs, The Voices (2014) perfectly showcases the ability of Reynolds to lead a project with charisma alone. The distinct delivery of his dialogue, the farcical expressions of his face — if it weren't for his performance, this premise would have likely come up short. Or extremely depressing, because, fair warning: it's a dark comedy, and by no means for the faint of heart.
It follows Jerry, a deranged factory worker who hears voices from his pets. His cat suggests he become a killer, while his dog leans toward the more average end of the day-to-day spectrum. This nutcase even communicates with a head he at one point severs, with his psyche depleting from there. He really should have taken his medicine.
8 The Adam Project
The most visually stunning movie on the list is The Adam Project (2022), a science fiction outing with Ryan Reynolds in the titular role. At least, he plays the older version of Adam Reed, who kicks off the plot by stealing a "time jet" to escape a dystopian 2050 and return to 2018. He's looking to save his wife, but things of course go wrong in the process, thus resulting in a funny yet poignant journey through time and space.
Sure, this isn't the greatest of screenwriting efforts — mostly due to lazy, inconsistent plot points — despite being penned by four creatives. But with great visual effects, charismatic performances and some entertaining dialogue, The Adam Project released to a massive reception, with audiences quickly bringing it into Netflix's top 10. It's well-made around every corner of production, and that includes its feats of comedy.
7 Pokémon Detective Pikachu
Reynolds lent his distinctively snarky voice to the fan-favorite pocket monster here in Pokémon Detective Pikachu (2019). Though typically known for combating fellow monsters, Pikachu here dons a deerstalker hat and picks up a magnifying glass to solve a mystery replete with well-written jokes and hilarious performances.
Though some can be a tad jarring, the visual designs of the Pokémon are often a sight to behold. But the design of Pikachu as a character, his idiosyncrasies, his dynamics, and his overall development — that's where Detective Pikachu shines, emphasizing its humor with an intelligent script focused on pacing and story structure. Rest assured that this delivers laughs while in tandem resonating as a story.
6 The Croods
In a lot of respects, The Croods (2013) is among the most underrated animated films made in recent decades. Considering the wit of its script, there's no telling how this DreamWorks outing holds only a 71% approval rating on critical consensus website Rotten Tomatoes, despite being Oscar-nominated. Good thing it made waves in theaters.
Audiences lined up en masse to see this prehistoric tale, in which a family of Neanderthals — voiced by well-known names like Nicolas Cage and Emma Stone — fight for survival while in search of a new home. Reynolds appears as Guy, an outsider to the family who guides them through the landscape and brings great comedic value to an already hilarious script. If you discarded The Croods as a potentially lackluster project from DreamWorks, it's time you gave it a shot.
5 Harold and Kumar Go to White Castle
Kicking off one of the best comedy trilogies ever made is Harold and Kumar Go to White Castle (2004). This is the film that put John Cho and Kal Penn on the map, playing the eponymous characters. But this is also among the more famous film roles from actor Neil Patrick Harris, who arguably steals the show.
There are also early performances from names like Malin Åkerman and Bobby Lee, Ryan Reynolds showing up as a male nurse. That's his credit. He shows up to a brilliant extent, as do the rest of the performers herein. This is one of the most quintessential stoner comedies ever made as Harold and Kumar get high and decide to eat at White Castle. The conflict? The closest establishment is over an hour away. The plot flourishes in laughs from there, rendering Harold and Kumar Go to White Castle one of the funniest films with Ryan Reynolds.
4 The Croods: A New Age
Ryan Reynolds has several sequels under his belt: take Hitman's Bodyguard's Wife, for example. That's been touched on, while another sequel is still to follow. Among the more acclaimed franchise features of his career would undoubtedly be The Croods: A New Age (2020), which earned even better reviews than the original. Animated studio DreamWorks has several franchises under their belt, and this entry means The Croods should be considered among their best.
It features their trademark style of visuals, with a well-written script and great name value among its cast. The film's plot picks up with the titular family of cavemen searching for yet another haven to live, but this time, they encounter a family (named the Bettermans) who have excelled at a slightly quicker rate on the survival spectrum of human evolution. An inventive premise for a sequel and a great execution means A New Age lands higher than its predecessor.
3 Deadpool 2
Really, the only reason Deadpool 2 (2018) comes up shy of the penultimate spot is because it was released in proximity to its predecessor. Amid dozens of other Hollywood superhero films, two back-to-back movies felt like the beginning of another franchise destined to fatigue its fans. For the most part, Deadpool 2 exceeded expectations, thus landing here at number three.
It's still a hilarious film with Ryan Reynolds, in other words, even if there's a film that separates the two. This is among the more refreshing sequels in recent memory, taking risks off the bat both in the plot and behind the scenes. It picks up two years after the events of the first film, with the events being just as famous as the Merc himself. This might always be the role that fans associate with Ryan Reynolds.
2 Free Guy
Perhaps a controversial pick for some fans, Free Guy (2021) comes in at number two on the list if not for the originality of its premise alone. He plays the titular protagonist (for whatever reason, Reynolds often plays characters named Guy) who discovers he's a non-playable character in an online role-playing video game. Again, one of the more fascinating premises you're likely to read about today. And somehow, just as impressive is the execution.
This is a shining example of an actor embodying their role, forcing audiences to look back in hindsight and wonder whether anyone else could have filled their idiosyncratic shoes. Reynolds shines as an NPC, with his mannerisms and intonations perfectly representing those you might see in Grand Theft Auto, for example. And sure, Free Guy isn't necessarily an excellent film aside from the wit of its script and the performance from Reynolds. But it's more than funny enough to warrant this spot at number two.
1 Deadpool
The funniest film from Ryan Reynolds has to go to the original Deadpool (2016). Thanks to its brilliant, genre-subverting style of breaking the fourth wall, he's able to use perfect timing with equally impressive conveyance to deliver the greatest performance of his career. He shines as the eponymous character, also known as Merc with a Mouth, with Deadpool also going down as perhaps the funniest superhero movie ever made.
There are many competitors in that regard. But from keen tactics of continuity editing to brilliant efforts of scriptwriting, this is a hilarious film thanks to various elements of behind-the-scenes filmmaking. And thanks to the convincing efforts of its star-studded cast (led by the man of the hour), Deadpool without a doubt deserves to top the list.