Best Chris Evans romantic comedy movies ranked: From Not Another Teen Movie to Before We Go, see which tops the list

Chris Evans, widely recognized for his iconic role as Captain America, has cultivated a remarkably diverse filmography that proves his range extends well beyond superhero territory. While the MCU cemented his global stardom, it was his early and ongoing roles in rom-coms that showcased a different side, captivating audiences seeking humor and tenderness. Below, we present the best Chris Evans romantic comedy movies ranked, reflecting on his varied career in the genre and highlighting what makes each performance memorable.

Chris Evans’ Romantic Comedy Journey

Before his superhero era, Chris Evans made a splash in romantic comedies, beginning with his major film debut in Not Another Teen Movie. Over the years, Evans has navigated a spectrum of leading and supporting roles in stories of love, heartbreak, and personal growth. With anticipation building around Materialists—where he stars with Dakota Johnson and Pedro Pascal—fans are eager to see him revisit the charm that originally made him a standout in rom-coms. Let’s explore every Chris Evans rom-com, ranked from cult classics to directorial debuts.

#8: Scott Pilgrim vs. The World (2010) – Evans as Lucas Lee

Directed by Edgar Wright, this film broke the mold with fast-paced humor and a fusion of animated visuals, quickly earning cult status. The narrative centers on Scott Pilgrim (Michael Cera) as he pursues Ramona Flowers (Mary Elizabeth Winstead), but must first face her seven formidable exes, portrayed in over-the-top, video-game-inspired battles. Chris Evans steps in as Lucas Lee, a swaggering action star with a penchant for fights. Although his appearance is brief, Evans’ performance is pivotal in one of the film’s most memorable showdowns. This ensemble cast, brimming with talented up-and-comers, makes the film a joy for spotting familiar faces—

“I didn’t know they were in this movie.”

—and connects cleverly to Evans’ later action hero reputation.

The film’s setting—a stylized Toronto—sets the stage for its surreal love story and outlandish confrontations, blending romance, comedy, and action in equal measure. Scott Pilgrim vs. The World showcases Evans’ adaptability and foreshadows his later forays into high-octane roles, but with an ironic, comedic twist that’s unmistakable.

#7: Playing It Cool (2013) – The Writer Who Can’t Write About Love

Under Justin Reardon’s direction, Evans plays a struggling screenwriter challenged to pen the ultimate romantic comedy, despite never truly experiencing love himself. The protagonist, known only as “Me,” becomes entangled with Ella (Michelle Monaghan), catalyzing his emotional awakening through the course of a quirky, self-referential romance. The film unfolds in a meta-movie fashion, tracing Me’s imaginative process as it intertwines his real-life journey and creative blocks.

Although the formula feels familiar and character depth is sometimes lacking, Playing It Cool allowed audiences to see Evans in a lighter, more vulnerable role distinct from his Marvel persona. A standout moment comes when Mallory candidly asserts,

“men and women can’t be friends”

—a nod to the genre’s classic debates. Sharing the screen with Anthony Mackie, fans found delight in the crossover of future Captain Americas and the broader Marvel alumni network. Ultimately, while not Evans’ strongest, the film is a breezy and watchable entry in his rom-com catalog.

#6: London (2005) – A Night of Regret and Lost Love

Helmed by Hunter Richards, London features Chris Evans in a performance tinged with pain, heartbreak, and dark humor. As Syd, Evans crashes his ex-girlfriend London’s (Jessica Biel) farewell party, spiraling into introspective dialogues fueled by drugs and alcohol alongside his dealer Bateman (Jason Statham). The film situates much of its weight in the cramped bathroom conversations, where Syd and Bateman confront themes of love, sex, faith, and failure.

London blurs the boundaries between romantic comedy and drama, prioritizing raw emotion and existential dread over easy laughs. While some critics felt the story veered too heavily into seriousness, the film revealed Evans’ capacity for portraying complex, wounded characters. Syd’s desperate attempts at closure, combined with his inability to move on, resonate deeply even as the film’s ambition seems to eclipse its execution.

#5: Ghosted (2023) – The Tables Turn on Gender Roles

In Dexter Fletcher’s Ghosted, Chris Evans takes on the role of Cole, a gentle soul who works at a farmer’s market and finds himself infatuated after a single date with Sadie (Ana de Armas). The film subverts expectations by casting Cole, not as the stoic rescuer, but as the one in need of saving when he discovers Sadie is actually a secret agent. Their second encounter throws Cole into Sadie’s perilous world, where mistaken beliefs about being ghosted quickly spiral into high-stakes espionage.

The dynamic between Evans and de Armas stands out for flipping traditional gender scripts; Evans’ character navigates vulnerability while De Armas takes the lead in action and decision-making. Ghosted marks the duo’s second collaboration following Knives Out, bringing playful chemistry to a genre that often trades in formulaic roles. The film explores the balance between connection and independence, and Evans capitalizes on the chance to challenge and expand his romantic persona.

#4: What’s Your Number? (2011) – Searching for Love in All the Old Places

Directed by Mark Mylod, What’s Your Number? follows the misadventures of Ally Darling (Anna Faris) as she embarks on a mission to reconnect with her previous nineteen ex-boyfriends in hopes of finding true love before reaching a self-imposed deadline. Evans plays Colin Shea, a supportive neighbor who reluctantly becomes Ally’s sleuthing accomplice in her romantic quest. The film draws inspiration from Sex and the City, reframing the anxiety and hope of women confronting milestones in their thirties.

This entry in Evans’ rom-com lineup doesn’t reinvent the genre, but the chemistry between Faris and Evans lifts the familiar plot. Evans’ role is supportive but significant—providing an emotional anchor as Ally’s journey yields unexpected revelations. Audiences embraced the film for its relatability and breezy humor, marking another notch in Evans’ diverse romantic journey.

#3: The Nanny Diaries (2007) – Navigating Privilege and Possibility

Co-directed by Shari Springer Berman and Robert Pulcini, The Nanny Diaries sees Evans share the screen with Scarlett Johansson, long before their Avenger days. Johansson stars as Annie Broderick, a college student balancing intense academic pressures with the demands of nannying for a wealthy New York family. Evans plays Hayden, better known as “Harvard Hottie,” who becomes Annie’s romantic interest amidst the chaos.

The film delves into the challenges of making it in New York, with Annie’s striving sharply contrasting Hayden’s privileged background. Their budding relationship forces both characters to reckon with compromise and growth. This collaboration marked the second time Evans and Johansson appeared together (following The Perfect Score), foreshadowing their enduring creative partnership. The Nanny Diaries serves as both a snapshot of mid-2000s city life and a record of Evans’ evolving versatility.

#2: Not Another Teen Movie (2001) – Satire and a Star-Making Debut

Directed by Joel Gallen, Not Another Teen Movie is an unapologetic parody that gleefully exaggerates every trope in the teen rom-com playbook. Chris Evans headlines as Jake Wyler, the archetypal jock who accepts a bet to transform the unpopular Janey Briggs (Chyler Leigh) into prom queen material. As the story progresses, the characters’ stereotypes peel away, revealing unexpected depth amidst the absurdity.

The film weaves together irreverence from comedies like American Pie, the classroom dynamics of The Breakfast Club, and the high school romance of 10 Things I Hate About You. Its humor verges on outrageous, but the movie’s underlying affection for its inspirations shines through. Evans’ magnetic, self-aware performance propelled his career forward and remains a fan favorite. Despite the risk of being typecast, he emerged from his debut with a career-defining role that continues to be celebrated today.

#1: Before We Go (2014) – Evans’ Directorial Vision of Love and Serendipity

Before We Go, directed by Chris Evans himself, stands as the pinnacle of his romantic comedy work. The film centers on Nick Vaughan, a struggling musician who meets Brooke Dalton (Alice Eve) in Grand Central Terminal after she misses her train to Boston and finds herself stranded in New York City with almost nothing to her name. Over the course of a single night, the two strangers form an intimate bond, each grappling with loss and searching for direction.

The narrative emphasizes slow-burning connection—mirroring classics like Before Sunrise—where two souls traverse the city, sharing the burdens and hopes they carry. Nick’s lack of purpose finds a new spark through the night’s events with Brooke, while she confronts her own dilemmas. Their relationship, though fleeting in the narrative, lingers with both characters and viewers as a meditation on timing, vulnerability, and chance. As Evans’ directorial debut, Before We Go reveals his capacity for depth and sincerity both in front of and behind the camera. The year 2014 saw Evans at the height of his visibility, but this film captured his essence as a brooding, open-hearted romantic far from the arenas of superhero spectacle.

Why Chris Evans’ Romantic Comedies Matter

Ranking the best Chris Evans romantic comedy movies reveals not just the diversity of his performances, but also the shifting landscape of the genre itself—from outrageous parody and genre subversion to nuanced explorations of love, self-discovery, and emotional honesty. Whether embodying satirical jocks, conflicted artists, or earnest romantics, Evans brings layered intensity and relatability to every role. His collaborations with notable co-stars like Anna Faris, Scarlett Johansson, and Ana de Armas only reinforce the impact of partnership and chemistry, both as narrative themes and audience draws.

With his upcoming role in Materialists alongside Dakota Johnson and Pedro Pascal, Evans signals a return to the roots that first brought him acclaim in romantic storytelling. As fans continue to seek authentic, engaging depictions of romance on screen, Evans’ evolving presence in the genre cements his place as a dynamic force, willing to challenge tradition and experiment with new forms of connection and comedy. The journey from Not Another Teen Movie to Before We Go underscores an actor willing to take chances and redefine the scope of what a romantic lead can be.