The 25 Best Romantic Comedies of All Time

18. I Love You, Man (2009)

I Love You, Man (2009)

One area of life that rarely gets explored in cinema is how difficult it can be to foster new friendships as an adult. What may have appeared to be an Apatow knockoff from the marketing campaign turns into a movie that is both heartfelt and creative. I Love You, Man utilizes many of the classic romantic setups, but in search of a platonic relationship.

The complexity of male social order is made even more pronounced through scenes with Jon Favreau’s character, who is the overly masculine aggressive minor role. As most well-made films in the genre, this movie is not only hilarious; it is sappy enough to be entertaining and conflicted enough to be compelling. Through the blend of witty dialogue and imaginative sight gags, I Love You, Man elicits genuine laughter throughout its runtime.


19. Away We Go (2009)

Away We Go (2009)

After he had crafted the artistic masterpiece American Beauty but before he had signed on to the high-grossing James Bond franchise, Sam Mendes gave the world this indie gem. Away We Go follow a moderately alternative couple (John Krasinski and Maya Rudolph) as they learn that they are about to be thrust into the struggles of parenthood.

Showing that unplanned pregnancy is not just something that plagues lascivious teenagers, these characters are well-read, cerebral, and genuinely display a mature love for one another. Throughout the film, we see a wide variety of outlooks on parental engagement as the leads form their own style in this department. The dramatic scenes are just as effective as the comedy, and the filmmakers are able to combine these elements in such a way that their story is relatable and enthralling.


20. (500) Days of Summer (2009)

(500) Days of Summer (2009)

Once a relationship has ended, we have a tendency to replay its key moments in our mind, normally in a distorted version that is anything but in correct sequence. This is precisely how this movie plays out, as Tom recalls the memories he had with Summer following their breakup. Seeing the world through his eyes, he see a rare male view of romantic entanglements.

Because it is happening within his imagination, the film is able to showcase its surrealist elements, perhaps most notable of which is the choreographed song and dance number with strangers on the street after Tom and Summer are first intimate. Men will find themselves able to relate to these quirks as Tom does not fall into the stereotypical male role of a romantic comedy; he feels like an authentic and complex individual. (500) Days of Summer is as much an argument for Romantic ideals as it is for realism.


21. Crazy, Stupid, Love (2011)

Crazy, Stupid, Love (2011)

In yet another example of gracefully interwoven love stories done right, Crazy, Stupid, Love tugs magic out of its talented ensemble cast without becoming convoluted or overstuffed. This movie is able to blend both the damage and the passion of romance, by looking at varied forms of relationships as seen at different points throughout life.

While there are unassumingly remarkable performance from just about every actor, it is Ryan Gosling who stands out as the suave playboy who is lovable despite his habitual womanizing. Because it shows many different views of love, it is difficult for the audience to not be able to latch on to at least one of those mindsets. Crazy, Stupid, Love respects its characters and approaches romantic relationships in a way that is hilarious without being raunchy.


22. The Five-Year Engagement (2012)

The Five-Year Engagement (2012)

Even when two people find happiness and maturity with one another, life can often get in the way. That is the premise of The Five-Year Engagement, as Jason Segel and Emily Blunt have to overcome conflicting career aspirations and other obstacles to prove their love to one another. The film’s greatest strength is that is centers around the idea that relationships take tremendous work and maintenance.

The leads create an amazingly realistic connection with one another and feel like an authentic couple, particularly in their arguments. Even at its most crude, this movie is able to stay true to reality through its vulgarity and it creates much more moving emotional scenes than its marketing campaign would suggest. The Five-Year Engagement benefits from its charismatic leads and its focus on the tension of relationships.


23. Ruby Sparks (2012)

ruby sparks

Ruby Sparks excels as it explores whether or not it is ideal to be able to craft a romantic partner to your own specifications. Paul Dano plays a writer who comes to terms with the fact that not only has his creation come to like, but he can alter any aspect of her being simply by typing his thoughts. As absorbing as it is philosophical, Ruby Sparks argues that perception of fantasies are best to be left just that.

True connection with others is built through the ugly bits that no one would think to include in their “perfect” partner. Ruby rarely reaches above the “manic pixie dream girl” trope because that is all her character is allowed to be. Depending on your emotional state when you watch this movie, it would be all too easy to relate to either of the leads.


24. About Time (2013)

About Time

While its advertisements showcase the romantic elements of this film, it is actually a far more encompassing film in its discussion of human nature. About Time follows a socially awkward but well-intentioned man as he learns that he has the ability to (though somewhat limited) travel back in time.

As is to be expected, he first uses his gift to win over a woman, in a way that is not as manipulative as it sounds. Because of this, the first half of this movie revolves around its romantic aspects. However, the rest of the film is steeped in the family dynamic. Some of the dialogue in this movie is so reflective and natural that it seems like there is a fair amount of improvisation from the actors.

Like any good time travel movie, About Time showed the limitations that the ability has, as well as the dangerous implications it can have if used thoughtlessly. After watching this film, audiences will be asked to evaluate how much of their life they are taking for granted.


25. What If (2014)

What If (2014)

In tackling one of the most prevalent questions of the genre (Can men and women ever be friends?), What If creates a movie that is enjoyable and all too relatable. The greatest strength of this film is its dialogue. Whether the characters are talking about fecal matter or bedroom habits, every line is witty and adds to the development of the leads as human beings.

This film doesn’t ask whether or not there is sexual tension when men and women form platonic bonds; it begins with the sexual tension and shows how that friendship continues to grow and transform in spite of it. Daniel Radcliffe and Zoe Kazan are both adorably fascinating, and their relationship is one that actually plausibly enough to demand the viewer’s support.

What If uses clichés to its advantage as it proves that simply because something is familiar doesn’t mean that it can’t be given glimpses of originality.

Author Bio: Brian Thompson currently resides in Chicago, where you can find him watching a matinee at Music Box or enjoying a book in the park. He also enjoys talking about movies on his blog: