Chris Evans’ Best Romantic Movies, Ranked

These days, it is nearly impossible to detach actor Chris Evans from his most iconic role: Steve Rogers, better known as Captain America. The actor made his first on-screen appearance in the Marvel Cinematic Universe in 2011, when he starred in Captain America: The First Avengerand subsequently took part in an impressive number of films, among them, the avengers saga. Prior to joining the Avengers, Evans himself was no stranger to superhero movies: his breakthrough role was also with Marvel Comics, starring as The Human Torch in Fantastic Four and its sequel, Fantastic Four: Rise of the Silver Surfer.

While Evans is a star widely associated with his signature superhero roles, his career is not just about that. Over the years, Evans has dabbled in many film genres and has performed a great range of characters. Among his most noteworthy projects are the drama giftedthe movies Knives Out and snow piercerand the documentary Superpower Dogs. Evans also gave directing a try, and by 2014, he directed the feature Before We Go. His most recent project was as the star of Disney’s latest movie, light yearwhich premiered in June 2022 and recounts the origin story of Buzz Lightyear, the legend who inspired the spaceman action figure from Toy Story.

Out of every genre Evans has ventured into, we can also find him starring in romances. Even though it is not so common to watch him as a heartthrob, he has some movies of this genre under his belt that are worth adding to your watchlist. Therefore, here is a selection of the actor’s best romantic movies throughout the years.


6 Playing It Cool

Playing It Cool is a 2014 romantic comedy film that stars Evans, Michelle Monaghan, Anthony Mackie, Aubrey Plaza, Patrick Warburton, Ioan Gruffudd, and Topher Grace. In the film, Evans stars as Me, a screenwriter eager to work in the action genre. However, his agent (Mackie, also his MCU co-star) assigns him to write for the one genre he wishes to avoid: romantic comedy. This young man doesn’t believe in love, and over the course of his life, every single one of his relationships has failed. That all changes when he meets Her (Monaghan), with whom he falls madly in love. But this relationship may not be as straightforward as he expects it to be: in spite of the obvious attraction between them, she is in a relationship with another man.

Related: Chris Evans Says He Can’t Return as Captain America: ‘The Role Is Anthony Mackie’s’

5 Not Another Teen Movie

Not Another Teen Movie is the sort of movie that any fan of teen rom-coms should watch at least once in their lifetime. Directed by Joel Gallen and starring Chyler Leigh and Evans, among other actors, this 2001 production parodies some classic teen movies, relying heavily on the plot of She’s All That, Varsity Blues and 10 Things I Hate About You, although, if one is attentive, references from more than 40 movies of the genre, especially from the 80s and 90s can be identified. In the film, the audience follows the story of Jake Wyler, the star of the school, who makes a bet with one of his friends that he can turn Janey Briggs, the school’s outcast, into the prom queen. But what Wyler doesn’t expect, as opposed to the audience, is that he will wind up starring in a love story with the girl. Besides featuring almost every cliché of the teen rom-com genre, the movie also showcases some of its stars, such as Molly Ringwald, Melissa Joan Hart and Paul Gleason.

4 What’s Your Number?

Evans and Anna Faris star in the 2011 rom com, What’s Your Number?, directed by Mark Mylod, as Colling and Ally, two neighbors with completely different lives. Ally is currently going through a rough patch: her boyfriend left her, she lost her job, and to top it all off, she read an article in Marie Claire magazine that states that women who have had more than 20 partners struggle to find a husband . After she finds out that she has already had 19 lovers, Ally decides not to get involved with any more men until she finds her true love. Collin, on the contrary, spends most of his days dating as many women as he can, but when he hears about Ally’s mission, he decides to help her track down her ex-partners one by one in order to find out if they could be a potential husband. Yet, love may be closer than they both think.

3 The Loss of a Teardrop Diamond

The Loss of a Teardrop Diamond is a 2008 movie starring Bryce Dallas Howard and inspired by Tennessee Williams’ screenplay. The story follows Fisher Willow, the daughter of a millionaire who struggles to find men to escort her to events. For this reason, she decides to hire Jimmy (Chris Evans), a low-income young man who works on her father’s plantation, as an escort to events, though she quickly falls in love with him. Jimmy, on the other hand, doesn’t seem to correspond to her love, something that angers her. Yet, their real problems begin when she loses a diamond earring she borrowed for an event, and implicitly accuses young Jimmy of stealing.

Related: Chris Evans is Open to Returning as Human Torch in the MCU

2 Before We Go

Before We Go is the 2014 film that marked Evans’ directorial debut. In this production, the actor also stars as Nick Vaughan, a street musician that one night, by a twist of fate, meets Brooke Dalton (Alice Eve). Brooke is a young woman having the worst night of her life: she missed her train back to Boston, her phone broke, and on top of it all, she was robbed. Attempting to help her, Nick ends up spending the whole night with her, and as time goes by, they learn a lot about each other. Will one night be enough for them to fall in love? In a segment of Variety Studio: Actors on Actors, Evans expressed his desire to direct another movie.

1 The Nanny Diaries

Shari Springer Berman and Robert Pulcini wrote and directed The Nanny Diaries, starring Scarlett Johansson and Chris Evans, one of the funniest duos in the MCU. In the movie, Johansson is Annie Braddock, a recent Montclair State University graduate who still doesn’t know what the future holds for her. After saving a young boy from being hit by a car, she lands a job as his nanny. However, this task is not going to be that easy, as the boy’s mother takes it upon herself to make her life miserable. Thankfully, Annie is helped by Hayden, a neighbor from the building with whom, after some initial clashes, she ends up falling in love.

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