Free Guy star Ryan Reynolds has several superhero roles under his belt, which range from some of the most infamous comic book adaptations to some of the best of all time. Reynolds is now known for his playful brand of humor and his penchant for high-octane action roles. However, he began his acting careers with lighthearted and comedic roles such as Billy Simpson in 1991’s Fifteen, Macro in The Odyssey, Seth in the Sabrina the Teenage Witch TV movie, and Michael “Berg” Bergen in Two Guys, a Girl, and a Pizza Place.

Reynolds then became the action-comedy heartthrob his fans know him as nowadays with higher profile roles like Mark Tobias in 2003’s action comedy remake The In-Laws, as well as Hannibal King in 2003’s heist movie Foolproof and 2004’s Blade: Trinity — his first-ever superhero performance. Despite having a bad streak with action movies like Blade: TrinityX-Men Origins: WolverineGreen Lantern, and the comic-book movie R.I.P.D., Reynolds was the perfect actor to portray a live-action Deadpool in Fox’s Deadpool and its sequel, Deadpool 2. Beyond superhero performances, Reynolds has found success with his starring roles in Hollywood movies like Detective Pikachu and Free Guy.

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Before Wade Wilson makes his highly-anticipated arrival to the Marvel Cinematic Universe with Deadpool 3, let’s take a look back at Reynold’s superhero roles and inspect what worked and what didn’t. Here’s every superhero the Deadpool star has played over the years.

5. Green Lantern

As one of the main members of the Justice League and one of the most famous superheroes in all of DC comics, it’s no wonder why there was so much anticipation before the release of 2011’s Green Lantern — so much so that Warner Bros. planned it to be the first installment in a franchise that promised to rival the MCU. Unfortunately, Green Lantern suffered from a flimsy script with awkward exposition and little substance. The visual effects were overwhelming, the action was often unintentionally comedic, and Parallax — who’s supposed to be one of the most menacing villains in Green Lantern’s mythos — was reduced to a cliché antagonist that seemed to be a parody of his comic book counterpart. All of these flaws also affected Reynold’s  performance, which didn’t seem serious or funny enough to stand out, despite being a rather inspired casting choice.

Reynolds himself has been vocal in his criticism of Green Lantern, going so far as to make fun of the movie in Deadpool 2‘s post-credits scene, where Wade Wilson time-travels to 2011 to shoot Reynolds before he accepted the role of Hal Jordan. Nevertheless, a rewatch one decade after Green Lantern‘s release can salvage some its strengths. The CGI, although oversaturated, seems ahead of its time at certain points. The scenes that take place at Oa are also ripped straight from the comics, and the performances and designs of characters such as Michael Clarke Duncan’s Kilowog and Mark Strong’s Sinestro are nothing less than excellent. Unfortunately for the character, it’s going to be difficult to shake off the sour taste of the Green Lantern movie anytime soon.

4. Blade: Trinity

After the unprecedented success of Blade and Blade II, expectations were high for the final installment in the trilogy, as fans wanted the Marvel property that breathed new life into comic book movies to end on a high note. However, the gritty action of the first two movies was absent from Blade: Trinity, which was inexplicably much campier and uneven. Much of the movie’s weaknesses were due to Wesley Snipes’ constant conflict with director David S. Goyer, which resulted in many last-minute changes. The tone and the pacing were all over the place, and much like Green Lantern, the movie’s serious moments were poorly blended with its comedy. Even though Ryan Reynolds’ first shot at a superhero movie was a failure, his role as Hannibal King in Blade Trinity was the first hint at his talent for action and comedy, which he would later use to succeed at playing Deadpool. Blade: Trinity doesn’t even seem like it takes place in the same franchise as its two predecessors, but gains certain charm if it’s watched with the intention of wondering how it came to be after many behind-the-scenes difficulties.

3. X-Men Origins: Wolverine

Long before Reynolds delivered one of the most highly praised superhero performances of all time as Wade Wilson in Deadpool, he had his first approach to the character in X-Men Origins: Wolverine. The 2009 movie promised to be the first in a series of spinoffs after the first X-Men trilogy, starting with Hugh Jackman’s Wolverine before moving on to Magneto. Yet, X-Men Origins: Wolverine failed to tell a self-contained story, opting to merge Wolverine’s origin with the first chronological appearances of other major characters such as Gambit, Cyclops, and Deadpool. Amongst the poor visual effects, unfocused story, and mishandling of various major characters, Reynolds’ Deadpool was one of the characters that suffered the most. Wade Wilson lacked his meta sense of humor, his taste for gory violence, and worst of all, he was turned into a gross amalgalm of mutants with varied superpowers and a surgically sealed mouth.

The only battle between Wolverine and Deadpool in the entire X-Men franchise was wasted, as Deadpool was completely unrecognizable. This was also made worse by the fact that Ryan Reynolds was replaced by Scott Adkins once Deadpool received his powers, and Scott Adkins’ performance was also obscured by a heavy layer of makeup and subpar visual effects. Of course, the movie has its moments, but they aren’t enough to salvage the rest. Deadpool and Deadpool 2 chose to ignore the events of the first Wolverine solo film, and plans for further X-Men spinoffs were cancelled after the failure of X-Men Origins: Wolverine, paving the way for X-Men: First Class instead.

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2. Deadpool

Despite the disappointment of X-Men Origins: Wolverine, Reynolds had already established that he was the perfect actor to portray Deadpool on the big screen, not only due to his proven acting chops and understanding of the character, but also due to his willingness to get him right. After all, Reynolds was interested in the project ever since 2004, working with Blade: Trinity director David S. Goyer to materialize a Deadpool solo movie. After several years of difficulties, Reynolds’ appearance on Tim Miller’s CGI test footage caused a spike in public interest to get the movie made. Fast-forward to the final product, and the movie ended up being as comic-accurate as the test footage, with a gory, hilarious, and fourth wall-breaking Deadpool tearing through hordes of nameless mooks. Reynolds action and comedy skills were finally done justice and, surprisingly, Deadpool had more heart than many other live-action comic book adaptations of its time.

Deadpool‘s unique take on superheroes brought on critical and commercial success. Its positive reception caused studios to have more faith in R-rated superhero movies, which inspired other similar blockbusters like David Ayer’s Suicide Squad and James Mangold’s Logan to target more mature audiences. Now, Deadpool is a landmark in the genre-blending superhero genre and a masterclass in choosing the right cast, the right tone, and the right amount of reliance on the artists’ vision.

1. Deadpool 2

Having found his footing as Wade Wilson, Reynolds doubled down on his performance with Deadpool 2. By 2018, Deadpool was already established as an extremely popular character and a bankable property. Therefore, Deadpoolhad an even more ambitious story with higher stakes, more action, and more violent comedy. Reynolds was also able to explore his spicy brand of humor in the Deadpool sequel, bouncing off the performances of Josh Brolin as Cable and Zazie Beetz as Domino. Deadpool 2 is relentless in its over-the-top tone and manages to feel just like a comic book while also letting audiences care for the characters’ journeys. While Green Lantern struggled to capture Hal Jordan’s appeal and Blade: Trinity couldn’t balance action and humor, Reynolds could venture into uncharted territory in Deadpool 2 by playing Juggernaut and Deadpool simultaneously, teasing viewers with Deadpool on the brink of death, and directly poking fun at the failure of Green Lantern and X-Men: Origins Wolverine. Although Disney’s acquisition of Fox stopped plans for an X-Force movie, there’s high hopes that Marvel Studios will harness Ryan Reynolds‘ talent to make Deapool a new staple of the MCU.

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