Ryan Reynolds has had an interesting career thus far as a performer. He’s an incredibly popular guy, and easy to love, but in some respects that "iconic role" remained elusive until Deadpool came along. He’s tackled various types of characters over the course of his career, from romantic leads to wisecracking comedic foils to yes, superheroes, but he's had a number of compelling and memorable performances that seem to go somewhat underrated. So we here at Collider wanted to look back and highlight the actor's most overlooked turns from years past.

Without further ado, Adam Chitwood, Allison Keene, Haleigh Foutch, and Chris Cabin present the most underrated performances of Ryan Reynolds’ career:

Mississippi Grind

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Image via TIFF

Anna Boden and Ryan Fleck have proven to be two of the more convincing purveyors of New Hollywood revivalism over the last decade, beginning with the Ryan Gosling’s breakout vehicle Half Nelson and continuing with the lovely Sugar. With Mississippi Grind, they show allusions to Hal Ashby’s Looking to Get Out and Robert Altman’s California Split in telling the story of Curtis and Gerry, two hopeless gamblers played by Ryan Reynolds and Ben Mendelsohn, respectively, who run a streak through the South while attempting to find financial redemption in lieu of the other sort. The tortured spirit of the film belongs to Mendelsohn but Reynolds is the crucial counter, a symbol of the beleaguered charm of a born gambler. Rather than play his character’s luck up as a magical ability, Reynolds allows quite a lot of himself come out in the performance, the type of person with a distinct talent for getting other people, strangers or friends, to open up and talk plainly. In one great scene, he has a seemingly improvisational discussion with a stranger at the horse track about his, er, less-than-stellar history with women. Matched with Mendelsohn, who is quiet and secretive, Reynolds evinces an enveloping, melancholic view of the erratic, unaccountable nature of luck, and brings out a remarkable amount of humanity in a character that could have come off as no more believable than a Leprechaun. - Chris Cabin

Just Friends

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Image via New Line Cinema

Reynolds first burst onto the scene thanks to his comedic skills, and they are on point in the sorely underrated romantic comedy Just Friends. The role is actually a perfect fit for Reynolds, as the dichotomy between his impossibly good looks and goofy comedic sensibility is put to good use as a formerly chubby, sensitive-type who is now a trim, successful music producer. Anna Faris also turns in great work here as a play on a Britney Spears-esque pop star, and she and Reynolds have fantastic chemistry. The film allows Reynolds to flex his physical comedy skills quite a bit and also accentuates his penchant for perfect timing, especially when it comes to the running gag with his character’s brother. And the “I Swear” lip sync is a fitting capper to this goofy, sweet, incredibly entertaining comedy. – Adam Chitwood

The Nines

The Nines came about at a time in Reynolds' career when the actor clearly wanted to prove he could do more than be the smug but charming funnyman. The first (and so far, only) feature film directed by Go and Big Fish scribe John August, The Nines is a strange little brew and an oft-forgotten gem of Reynolds' filmography. Reynolds stars in a triplicate of roles -- a Hollywood actor in the midst of a downward spiral, a screenwriter struggling to get his pilot off the ground, and a family man on the path to life-altering self-discovery -- and he does them all without relying on the well-trod stereotypes or cliches. Thanks to August's unconventional script, which reaches some peak metatextual moments, The Nines is a bit of a head trip at times -- one that hinges on the audience taking an empathetic journey with Reynolds' characters as he guides us through the shifting perspectives of the film's narrative. Reynolds handles the task deftly, navigating between the surrealities and getting to the emotional truths. A particular second-act confrontation with Melissa McCarthy's character Melissa McCarthy (remember when I said this movie is strange?) is still some of the finest dramatic character work of his career. The Nines isn't perfect, nor is Reynolds' performance in it, but it's the kind of exciting and invigorated work that comes about when a filmmaker and actor are both trying to show the world what they can do. -Haleigh Foutch

Two Guys, a Girl, and a Pizza Place

ABC’s late 90s Gen X comedy Two Guys, a Girl, and a Pizza Place (later retitled Two Guys and a Girl after the pizza place was ditched) wasn’t one TV’s great works of art, but it did have its moments. Most of those moments revolved around the character Berg, played by Ryan Reynolds, who was bumped up to the show’s romantic lead once the producers realized they had, you know, Ryan Reynolds. The show followed a group of twentysomethings living in Boston, with Reynolds playing a glib medical student who, as the seasons wore on (4 in total), became an increasingly dynamic character. Even though this is one of Reynolds’ earliest roles, it’s clear in watching old episodes that he always had a defined and unique sense of performance, with his signature, exaggerated delivery, commitment to physical comedy, and natural sarcasm all intact. Ultimately, Reynolds used those comedic chops to great effect in this strange little series to really elevate it from a rote sitcom to something more. — Allison Keene

Buried

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Image via Lionsgate

Reynolds isn’t above gimmicks in films, whether in the premise or in terms of plot turns, but he’s the sort of performer who can ease the sting of such cheap simplicity. This is most noticeable in this experiment in terror from Rodrigo Cortes, which sets the actor as a contractor who has been buried alive for unknown reasons. The film is essentially a duet, with Reynolds creating a variety of linguistic and physical maneuvers to match Cortes’ series of aesthetic tests, from the use of a glowing cellphone to the horror of a black screen accompanied only by pants, grunts, screams, and pleas. The miraculous thing about this miniature thriller is that, by the end of it, Cortes and Reynolds have pushed the material beyond the trap of mere narrative trickery and have created a weirdly effective study of dread and death that never overplays the helplessness of the situation bur rather focuses on the inventiveness of the human mind in crisis. - Chris Cabin

Adventureland

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Few coming-of-age films have the sense of intimacy, yearning, and confusion that Greg Mottola’s Adventureland does, anchored as it is by one of Jesse Eisenberg’s best performances and centered on his character’s frustrated summer working at the titular amusement park. The frequently underrated Kristen Stewart plays the sardonic woman who bewitches him and their fumbling romance makes up the glut of the film, with Reynolds playing one of their bigger hurdles – the park’s maintenance man and Stewart’s character’s married lover. Reynolds is quieter than usual in this performance, suggesting a man who knows how charming he is and where his talents are limited in terms of intellect and ambition. With little more than delivery and subtle physicality, the actor hints at the lifetime of a former high-school heartthrob, where a fear of the world outside one’s hometown has curdled into indifference and cynicism. And yet, it’s easy to see why Eisenberg’s character remains friends with the guy, as he has a breezy yet firm hold on his machismo, and the ability to concede when he’s clearly losing the moral game. When we last see him, he’s still flirting with other, much younger women, telling a bunko story about meeting Lou Reed, and Mottola shows a confidence in leaving his story there, stuck in perpetual tailspin but never above enjoying the ride down. - Chris Cabin

The Voices

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Lions Gate Entertainment

This one’s actually not too old, and it might just be Reynolds’ best performance to date. Director Marjane Satrapi’s delightfully insane dark comedy The Voices follows a mild mannered man who not only has lengthy conversations with his dog and cat, but also has a tendency to murder the people around him after some urging from said companions. Reynolds masterfully walks the tightrope between pitiful and abhorrent, as the film is presented almost entirely from his character’s warped point of view. Reynolds is at once sweet, hilarious, terrifying, loathsome, and helpless, and on top of terrifically bringing the central character to life, he also provides the voices for his aw-shucks dog and mischievous cat. Released only last year, The Voices seems destined to find a cult following in the years to come, at which point hopefully Reynolds’ outstanding work will finally get its due. – Adam Chitwood

The Proposal

Perhaps a strange pick for Reynolds' underrated performances considering it's one of his highest-grossing films, but then again, it's not really his film, is it? And that's how The Proposal sneaks on the list. Reynolds has the on-screen presence to go toe-to-toe with Sandra Bullock, America's sweetheart and reigning queen of romantic comedies, and Betty White, everyone’s favorite human, and walk away with some of the movie’s biggest laughs. So often cast as the loudmouth who gives everyone shit, The Proposal proves Reynolds can be just as funny when the dynamic shifts and he's the one taking the abuse. It might also be the film that best demonstrates he's one of the few actors who can perform as the romantic lead and the comedic relief at the same time. He can turn up the charm just as quickly as he can deliver a laugh, and having built up an arsenal of comedic skills over his career, he can earn big laughs out of small moments, making the most out of somewhat generic material with pitch-perfect line-readings and gestures. It's easy to chalk up the success of The Proposal to the force of Bullock's presence, but that seriously undersells Reynolds' contribution to the chemistry and comedy that hit big with audiences. -Haleigh Foutch