Mississippi Grind is a character-driven drama about two gamblers, a seasoned but down-on-his-luck veteran (Ben Mendelsohn) and a charismatic but impulsive younger player (Ryan Reynolds), who team up for a road trip through the American South to try and change their fortunes. Reynolds delivers a more subdued and nuanced performance here, playing a character whose charm masks deeper vulnerabilities. The film is a slow-burn, atmospheric journey into the world of addiction and hope, focusing on the dynamic between the two leads. It's a departure from Reynolds' mainstream work, offering a glimpse into his capabilities in more dramatic and independent fare, reminiscent of classic gambling films.

Adventureland is a coming-of-age comedy-drama set in the summer of 1987, where a recent college grad takes a miserable job at a local amusement park. Ryan Reynolds plays Connell, a charming but married park technician who is the object of affection for Kristen Stewart's character. While not the main protagonist, Reynolds provides a layer of complexity and subtle sadness to his role as the older, seemingly cool guy who might not be everything he appears. The film is praised for its authentic portrayal of young adulthood, summer jobs, and awkward romance, with a fantastic soundtrack to match the era. It's a more understated role for Reynolds, showcasing his ability to contribute effectively to an ensemble piece with a strong indie sensibility.

Waiting... is a raucous ensemble comedy set over the course of a single shift at a dysfunctional chain restaurant called Shenaniganz. Ryan Reynolds is part of the eclectic staff, dealing with annoying customers, bizarre coworkers, and the general madness of the food service industry. While an ensemble piece, Reynolds gets plenty of moments to shine with his signature comedic timing and sarcastic delivery. The film captures the chaotic and often gross reality of working in a restaurant with a mix of relatable frustrations and over-the-top antics. It's a cult classic for anyone who's ever worked in food service and can appreciate the dark humor of the experience.

The Voices is a dark, quirky, and unsettling horror-comedy starring Ryan Reynolds in a truly unique role. He plays a seemingly sweet but troubled factory worker who, encouraged by his talking cat and dog, descends into a series of bizarre and violent acts. Reynolds voices both the cat (Mr. Whiskers) and the dog (Bosco), creating a disturbing and darkly humorous internal dialogue for his character. The film is a tonal tightrope walk, blending genuine psychological horror with moments of twisted comedy, all anchored by Reynolds' surprisingly nuanced performance as a man grappling with severe mental illness. It's definitely not for everyone, but it's a fascinating showcase of his willingness to take risks.

National Lampoon's Van Wilder is the movie that truly put Ryan Reynolds on the map as a comedic leading man. He plays the titular character, a seventh-year college student who has no intention of graduating, preferring to help others with their problems while living the ultimate party lifestyle. Reynolds' natural charisma and quick wit shine in this role, establishing the charming slacker persona that would become a staple in some of his future comedies. The film is a quintessential early 2000s college comedy, full of gross-out humor and ridiculous situations. It's a fun, albeit silly, look back at the beginning of his rise to stardom.

Green Lantern is Ryan Reynolds' first foray into the world of DC superheroes, where he plays test pilot Hal Jordan who is chosen by a mysterious alien ring to become a member of an intergalactic police force. While the film itself had a mixed reception, Reynolds' portrayal of the cocky yet ultimately heroic Hal Jordan was praised. The movie attempts to build a large cosmic universe, introducing concepts like the Green Lantern Corps and their power source. Despite its flaws, it's a significant chapter in Reynolds' career trajectory towards becoming a superhero icon, albeit not in the way he might have initially planned. The film's CGI was a major focus, aiming to bring the unique look of the Lanterns to life.

Just Friends sees Ryan Reynolds undergoing a hilarious transformation from an overweight, friend-zoned high schooler to a successful, but still emotionally stunted, music executive. When he's stranded in his hometown for Christmas, he reconnects with his high school crush, played by Amy Smart, who still sees him as just a friend. The film is a fun, often outrageous, holiday-themed romantic comedy that leans heavily into physical comedy and Reynolds' ability to play both the awkward and the overconfident sides of his character. Anna Faris also provides scene-stealing laughs as a truly eccentric pop star. It's a goofy, feel-good movie about escaping the friend zone.

Definitely, Maybe is a charming and clever romantic comedy structured around a father telling his daughter the story of how he met her mother, but changing the names so she has to guess which woman is the one. Ryan Reynolds plays the dad, Will, recounting his past relationships with three different women (played by Isla Fisher, Rachel Weisz, and Elizabeth Banks). The film is witty, heartfelt, and refreshingly non-linear, keeping the audience guessing along with the daughter. Reynolds brings a genuine warmth and sincerity to the role, making Will's journey through love and heartbreak relatable and engaging. It's a sweet story about finding 'the one', even when you're not sure who that is.

Buried is perhaps one of Ryan Reynolds' most challenging and unique performances. The entire film takes place inside a coffin, where his character, a truck driver in Iraq, wakes up with no memory of how he got there, armed only with a Zippo lighter and a cell phone. Reynolds carries the entire movie on his shoulders, delivering a tour-de-force performance filled with fear, desperation, and dwindling hope. The film's premise is claustrophobic and intense, relying solely on Reynolds' ability to convey the terror and frustration of his situation through phone calls. It's a gripping psychological thriller that proves his range as an actor.

Safe House throws Ryan Reynolds into the intense world of espionage as a rookie CIA agent stationed at a safe house in Cape Town, South Africa. His quiet posting is shattered when Denzel Washington's legendary and dangerous rogue operative is brought in. When the safe house is attacked, the two are forced to go on the run together. This film is a gritty, fast-paced thriller that showcases Reynolds holding his own against the formidable presence of Denzel Washington. The action sequences are raw and realistic, and the tension is palpable as they try to survive and figure out who is hunting them. It's a departure from Reynolds' usual comedic roles and proves his capability in dramatic action.

Prepare for explosive chemistry and non-stop banter in The Hitman's Bodyguard. Ryan Reynolds plays a perfectionist protection agent assigned the unenviable task of safeguarding a notorious hitman, played by the legendary Samuel L. Jackson, who needs to testify against a dictator. The dynamic between Reynolds' tightly wound character and Jackson's foul-mouthed, chaotic assassin is the heart of this action-comedy. Their constant bickering and grudging respect provide endless entertainment amidst high-octane chase scenes and shootouts across Europe. The film really lets both actors play to their strengths, resulting in a buddy action flick that's genuinely funny and thrilling.

Step aside, romantic comedy norms! The Proposal pairs Ryan Reynolds with the incredible Sandra Bullock for a laugh-out-loud story about a high-powered editor forcing her assistant into a fake engagement to avoid deportation. The chemistry between Reynolds and Bullock is absolutely electric and carries the film beautifully. Watching their characters hilariously navigate awkward family introductions and unexpected feelings in Alaska is pure joy. Bet you didn't know the iconic scene where they accidentally run into each other naked was entirely improvised by the two leads? Their comedic timing is impeccable, making this a genuine standout in the genre. It's warm, funny, and features some truly unforgettable moments.

Picking up the chaotic reins from its predecessor, Deadpool 2 somehow manages to up the ante on the absurdity, action, and emotional beats. Ryan Reynolds is back in peak form, delivering rapid-fire jokes and questionable life choices as Wade Wilson. This sequel introduces fantastic characters like Cable, played with stoic perfection by Josh Brolin, and Domino, whose luck-based powers make for some truly unique action sequences thanks to Zazie Beetz's effortless charm. The film leans even harder into breaking the fourth wall and self-referential humor, unafraid to poke fun at its own studio, other superhero franchises, and cinematic tropes. It's a wild, hilarious, and surprisingly touching ride that solidifies Deadpool's place as a unique force in cinema.

Get ready for a superhero movie unlike any other! Deadpool exploded onto the screen with its R-rated humor, fourth-wall-breaking antics, and Ryan Reynolds absolutely embodying the Merc with a Mouth. This wasn't just another comic book adaptation; it was a passion project for Reynolds, who spent years trying to get it made after his less-than-ideal turn as the character in X-Men Origins: Wolverine. The film's unexpected massive success proved that audiences were hungry for something irreverent and fresh in the superhero genre. It's packed with sharp wit, brutal action, and a surprising amount of heart nestled beneath all the potty humor. Seriously, the dedication Reynolds showed to bringing this character to life is truly inspiring, and it completely paid off!