The 20 Best Movies To Watch If You Like (500) Days Of Summer

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The acclaimed 2009 comedy "(500) Days of Summer," memorably starring Joseph Gordon-Levitt and Zooey Deschanel, is widely considered a love story, despite the movie explicitly denying this association. As its lead actors maintain, the film is more of a coming-of-age tale than a conventional romance, with its protagonist confronting the truth about the nature of love. For those who enjoy the movie's quirky sense of humor, eclectic soundtrack, and refreshingly grounded and related performances, there are several thematically similar films. While some of these comparable movies are outright romantic comedies, what really links them to "(500) Days of Summer" are their young adult coming-of-age sensibilities.

This isn't to say that these movies are directly inspired by "(500) Days of Summer" either; several on this list were released years before. What these movies have in common is a wry, often self-aware and dialogue-driven sense of humor, with the story anchored by two likable leads. And, in quite a few of these films, the soundtrack not only organically fits into the narrative but elevates the entire viewing experience. Here are the best movies to watch if you like "(500) Days of Summer."

After playing a hopeless romantic in the '80s classic "Say Anything," John Cusack's starring role in 2000's "High Fidelity," is the actor at his most relatably down-to-earth. Based on the Nick Hornby novel of the same name, Cusack plays Rob Gordon, a man working at a small record store in Chicago. Following a breakup with his latest serious girlfriend, Rob begins mentally revisiting all his past major relationships as his life reaches another personal crossroad. As Rob ponders his life's romantic failures, he addresses the audience directly while the employees at the record store serve as a Greek chorus to his story.

Co-written by Cusack himself, "High Fidelity" is the ultimate showcase for his dry humor and outlook on life, love, and, of course, music. Cusack leans into his laidback everyman charm while Jack Black delivers a scene-stealing performance as his friend and co-worker Barry. If "(500) Days of Summer" is about reevaluating life and relationships in one's late 20s, "High Fidelity" is about doing so in one's 30s. Led by Cusack and Black at their most likable, and powered by a killer soundtrack, "High Fidelity" is an understated masterpiece.

Breakups can be so painful that one might catch themselves wishing any lingering memories from a ruptured romance were erased completely. That desire informs the 2004 romantic drama "Eternal Sunshine of the Spotless Mind," set in a world where people can pay to have unwanted memories removed. After Joel (Jim Carrey) learns that his ex-girlfriend Clementine (Kate Winslet) has had her memories of him erased, he decides to undergo the same procedure. As Joel undergoes the memory erasure, he relives his history with Clementine and reconsiders whether he wants to forget her forever.

Intentionally disorienting and surreal in the uneven exploration of its protagonist's memories, "Eternal Sunshine of the Spotless Mind" has Carrey's best dramatic performance to date. Matching him is Winslet as a grounding presence to the raw vulnerability Carrey brings to his lovelorn role. Reveling in its bittersweetness, "Eternal Sunshine of the Spotless Mind" has a dream-like quality that helps ease the story's inherent sadness. Starting under the auspices of heartbroken cynicism, the film rediscovers the value of sentimentality rather than casting complicated emotions into clinical oblivion.

The middle installment of filmmaker Richard Linklater's Before trilogy, 2004's "Before Sunset" is the sequel to "Before Sunrise." Nine years after their romantic night in Vienna, star-crossed couple Jesse (Ethan Hawke) and Céline (Julie Delpy) reunite for an afternoon in Paris. Though the two have moved on separately, with Jesse having since become a successful author and family man, they still remember their magical time together. As the two catch up strolling through the French capital, they realize by the ending of "Before Sunset" that their feelings for each other may not be entirely in the past.

"Before Sunset" features beautifully staged scenes that take full advantage of having Paris as a backdrop. Presented as one long conversation, the movie keeps the proceedings focused tightly on Jesse and Céline, with Hawke and Delpy's easygoing and natural chemistry stronger than ever. The longer takes and camera following the actors through Paris makes the viewer feel like they're part of the conversation, if only as a constant observer. A love story for 30- and 40-somethings disillusioned with how their life has gone, "Before Sunset" is the pinnacle of Linklater's trilogy.

Young love and effervescently poppy melodies blend together seamlessly in the 2008 romantic comedy "Nick & Norah's Infinite Playlist." Adapting the 2006 young adult novel of the same name by Rachel Cohn and David Levithan, the story takes place largely within a single night in Manhattan. After enduring a breakup, teenager Nick (Michael Cera) goes to New York to play with his band and find a secret show played by a popular indie band. He meets Nora (Kat Dennings), who joins him on his quest as they bond over music and find themselves falling in love.

"Nick & Norah's Infinite Playlist" captures that reckless abandon of being young and dreamily idealistic in the city, feeling as though anything is possible. Like their characters, Cera and Dennings play off of each other well, making the most of the dialogue-driven material. In lesser hands, the film could've felt like cloying young adult material, but it breathes new life into familiar tropes. Backed by a killer soundtrack, "Nick & Norah's Infinite Playlist" is a feel-good coming-of-age movie that makes Manhattan look like a lit-up playground.

Two years after starring in "(500) Days of Summer," Joseph Gordon-Levitt teamed with friend and creative collaborator Seth Rogen to headline the 2011 comedy "50/50." Gordon-Levitt plays Adam, a 20-something journalist in Seattle who is diagnosed with a rare spinal cancer. Given a 50% probability of survival, he endures a grueling chemotherapy regimen, attended to by his best friend Kyle (Rogen). As Adam confronts his own looming mortality, his relationship with his therapist Katherine (Anna Kendrick) begins to grow more personal than professional.

"50/50" faces its subject matter with the due seriousness required while managing to provide a surprising number of laughs for a story revolving around cancer. The entire ensemble cast delivers their performances perfectly, including Anjelica Huston as Adam's mother, but Gordon-Levitt is the major standout. Cancer forces Adam and Kyle to grow up, with their friendship forming the movie's emotional core. Balancing tragedy and comedy, "50/50" is an earnest and funny look at the transformative power of mortality and severe illness.

The life of a traveling stand-up comedian can be a monotonous grind of cheap hotels and dingy comedy clubs, the likes of which are explored by 2012 indie comedy "Sleepwalk with Me." A semi-autobiographical story co-written and directed by Mike Birbiglia, Birbiglia stars as Matt Pandamiglio, an aspiring comedian who suffers from a chronic sleeping disorder making him sleepwalk in a deep sleep. As Matt's career begins to take off, it leads to him and his longtime girlfriend Abby (Lauren Ambrose) reevaluating their relationship. This stress worsens Matt's sleepwalking condition, as his life reaches an important crossroads and he finds his comedic voice.

Birbiglia's understated comedic sensibilities and everyman qualities really help ground "Sleepwalk with Me" compared to flashier movies examining the lives of stand-up comics. There is a relatability to Matt's story, particularly for people approaching their 30s facing bigger life decisions and questions of commitment. "Sleepwalk with Me" also boasts a stacked ensemble cast, including supporting roles for Marc Maron, Kristen Schaal, and Carol Kane, all providing memorable performances. A beautifully stripped-down and intimate portrait of life on the road as a stand-up comedian, "Sleepwalk with Me" balances coming-of-age melancholy with earnest laughs.

The long, complicated road to the end of what once was a promising romance is the centerpiece of 2012's "Celeste and Jesse Forever." After high school sweethearts Celeste (Rashida Jones) and Jesse (Andy Samberg) marry young, they eventually drift apart and decide to divorce. This fissure is derailed as Jesse and Celeste each contemplate reconciling at different stages of the divorce and find love elsewhere. As the dissolution of their marriage grows more convoluted, the chances of them splitting amicably grows less likely.

Running for 92 minutes, there isn't an inch of celluloid filler on "Celeste and Jesse Forever" as it unravels its central couple. The movie never really asks the viewer to take sides on the split, with Jones and Samberg remaining likable throughout. With that in mind, the actors also display amounts of emotional depth and nuance they hadn't really demonstrated on-screen before or, arguably, since. Finding the charm in an ugly scenario, "Celeste and Jesse Forever" is one of the most pleasant divorce movies around.

Before she was helming billion-dollar blockbusters like "Barbie," filmmaker Greta Gerwig co-wrote the 2012 dramedy "Frances Ha" with director and partner Noah Baumbach. When protagonist Frances Halladay (Gerwig) is forced to relocate from her Brooklyn apartment, she bounces between friends and accommodations as she tries to adapt. This forces Frances to reevaluate her own life choices, amplified when she returns to her hometown of Sacramento. Faced with this deep existential crisis, Frances compares her own experiences with her close friends as they face their own challenges.

Like its flighty protagonist, "Frances Ha" flits around its narrative, alternating between tone and vignette as Frances finds her way. The movie's cinéma vérité influences are clear, particularly with its black-and-white cinematography evoking New Wave French and Italian movies from the '60s. What keeps "Frances Ha" from descending into self-indulgence is Gerwig herself, both with her writing and standout performance. With Gerwig front and center, "Frances Ha" rises above its contemporaries as the existential dramedy for any coastal 20-something woman who feels adrift.

Author Stephen Chbosky adapts his own 1999 best-selling novel "The Perks of Being a Wallflower" with a 2012 movie of the same name. Set in 1991 in a suburb of Pittsburgh, the film follows Charlie (Logan Lerman), a teenager suffering from severe clinical depression, as he begins high school. Charlie finds kindred spirits in senior siblings Patrick (Ezra Miller) and Sam (Emma Watson), joining their misfit ensemble of friends. As this friend group faces various hardships throughout the school year, the source of Charlie's deep-seated pain begins to come to light.

While the core trio of Lerman, Watson, and Miller are absolutely magnetic in their performances, "The Perks of Being a Wallflower" also features an incredible ensemble cast. One of the standouts is Paul Rudd, in one of his finest performances to date, as Charlie's English teacher, offering a subtly nuanced role while maintaining his usual easygoing charisma. Refreshingly sincere, the film really captures the feel of being an overlooked outsider, regardless of setting. Beautifully executed, "The Perks of Being a Wallflower" is an all-around tour-de-force for its cast and crew, and it's an essential movie about high school you need to see.

Advanced technology provides a cure for loneliness, if only for a limited time, in the 2013 science fiction romance movie "Her." Written, directed, and co-produced by Spike Jonze, the film is set in a near-future Los Angeles, following a well-meaning but profoundly lonely man named Theodore (Joaquin Phoenix). To cope with his solitude and depression, he purchases a virtual assistant artificial intelligence that takes on the name Samantha (Scarlett Johansson). As Samantha becomes more self-aware, she and Theodore fall in love while facing the obvious complications of their unique coupling.

A meditation on loneliness in the digital age, "Her" isn't so much an exploration on the nature of artificial intelligence as it is about how we learn to love. As technologically connected as Theodore is, it separates not just from finding another human romantic partner but also from his own humanity. It's through Samantha that Theodore is able to grow and emerge from his self-imposed solitary shell. Melancholy and yet hopeful, "Her" feels intensely personal, with Phoenix delivering one of his best performances of all time.

The lifespan of a romantic relationship is displayed in full in the 2014 indie dramedy "Comet," written and directed by "Mr. Robot" creator Sam Esmail. After meeting her at a meteor shower, self-centered protagonist Dell (Justin Long) strikes up a romance with the compassionate Kimberly (Emmy Rossum). The narrative is then told out of chronological order, showing Dell and Kimberly's relationship growing more serious before falling apart on more than one occasion. This dynamic unfolds over the course of six years, with Dell coming to terms with his own deep-seated narcissism in the face of the more empathetic Kimberly.

Like "(500) Days of Summer," the heavy use of flashbacks and flash-forwards throughout "Comet" keeps the viewer guessing about its core couple's fate until the end. Dell is a much less sympathetic protagonist than many of the other movies on this list, by design. Matching Long's antisocial energy as Dell is the always luminescent Rossum as Kimberly, with the pair taking the material to another level. More of an outright drama than a romantic comedy, "Comet" is about someone learning to look beyond themselves at a steep personal cost.

Indie filmmaker Noah Baumbach has built up an impressive filmography of postmodern romantic dramas and comedies, including more mature main characters reevaluating their place in life and love. Baumbach's 2019 drama "Marriage Story" follows married couple Nicole (Scarlett Johansson) and Charlie (Adam Driver) as their marriage steadily breaks down. What starts as an intent to divorce with little drama quickly devolves into a grueling process where Nicole and Charlie's ugliest qualities surface. This expands to custody battles over their son and suspicions that Charlie secretly cheated on Nicole prior to their separation.

"Marriage Story" feels like Baumbach's most personal film to date, with parallels to his own divorce prior to making the movie. In Adam Driver, Baumbach finds something of a muse and proxy protagonist, with Charlie veering between searingly vulnerable and emotional. While "Marriage Story" is one of Baumbach's more serious examinations of love, or rather its decay, there are still plenty of darkly comical moments throughout the movie. "Marriage Story" earned its cast and crew some of the biggest award season accolades to date, and rightfully so.

Let's address the elephant in the room first by acknowledging that filmmaker Woody Allen is a deeply problematic figure with numerous allegations against him. While it's understandable that some can't separate art from its artists, he has also made some of the most enduring comedies of all time. The most celebrated of these is Allen's 1977 Best Picture-winning romantic comedy "Annie Hall," with the neurotic Alvy Singer (Allen) left pondering his break-up with serious girlfriend Annie Hall (Diane Keaton). Alvy recounts the lifespan of his relationship with Annie, from their early dates, awkward cohabitation, and attempts at a reconciliation.

Like "(500) Days of Summer," Allen isn't so much crafting a love story with "Annie Hall" as he is meditating on romantic decay. Allen and Keaton's chemistry is palpable, with both characters likable, all things considered, but their break-up is already a foregone conclusion. At the same time, Allen keeps the proceedings light as he experiments with the medium, including celebrity cameos and breaking the fourth wall before it was cool. Regarded as one of the funniest screenplays ever written, "Annie Hall" emerges from the problematic shadow of its creator.

When it came to coming-of-age movies in the '80s, nobody consistently did it better than the Brat Pack ensemble of young actors. By the mid '80s, the Brat Pack had progressed to starring in stories about young adulthood rather than the high school movies that made them famous. One of the standouts from this period is 1986's "About Last Night" starring Rob Lowe and Demi Moore as young couple Danny Martin and Debbie Sullivan. Initially just a string of casual flings, a longer lasting romance forms between the two as they navigate their burgeoning relationship.

Like so many Brat Pack movies, the primary appeal in "About Last Night" is in its young and charismatic lead actors. Lowe and Moore's characters make a fine couple and one that the audience readily roots for, even as they stumble when things between them get serious. These are protagonists no longer dealing with puppy love but something more mature, and the movie wonderfully illustrates this. Sexy and sweet all at once, "About Last Night" captures its lead actors at a crossroads, with Moore delivering a particularly strong performance.

Just because a movie has a clear sense of whimsy doesn't mean that it amounts to little more than empty calories. A prime example of this is the 2001 French romantic comedy "Amélie," starring Audrey Tautou as the titular protagonist Amélie Poulain. A latchkey child with a vivid imagination, Amélie decides to devote herself to bringing happiness to those around her in Paris. As Amélie embarks on her idealistic quest, she finds love herself with a young man named Nino Quincampoix (Mathieu Kassovitz).

One of the all-around delightful movies ever made, "Amélie" is a clear reminder that not all coming-of-age stories need melodramatic stakes. There are emotional moments throughout the movie, to be sure, but they're never framed in a cataclysmic way but rather as part of a greater slice-of-life. Anchoring the whole thing is an effervescent Tautou, who effortlessly brings all the wide-eyed wonder and innocence that her role requires. An idyllic vision of Paris and the colorful residents within it, "Amélie" is sentimental movie-making magic.

After starring in a string of successful comedies throughout the '90s, Adam Sandler pivoted to his first major dramatic project with 2001's "Punch-Drunk Love." Written, directed, and produced by Paul Thomas Anderson, the movie stars Sandler as Barry Egan, a man with deep-seated anxiety and anger issues. Barry emerges from his isolated shell to begin a tentative romance with Lena Leonard (Emily Watson), one of his sister's co-workers. This is complicated by Barry being extorted from people connected to a phone sex line Barry called to cope with his immense loneliness.

After helming more expansive ensemble pieces, "Punch-Drunk Love" marks Anderson narrowing his focus to make a romantic comedy as only he could. With the amount of quiet emotional vulnerability and complexity that he brings, Sandler delivers his best serious performance to date, a distinction that remains over 20 years later. There are still funny moments throughout the movie to be sure, but a heightened sense of unpredictability and a more grounded menace under the surface. A well-executed pivot to more intimate fare for Anderson, "Punch-Drunk Love" is among both he and Sandler's more overlooked work.

In the midst of starring in the successful sitcom "Scrubs," actor Zach Braff wrote, directed, and starred in the 2004 dramedy "Garden State." Braff plays Andrew Largeman, who returns to his New Jersey hometown after the death of his mother, reuniting with his estranged psychiatrist father Gideon (Ian Holm). As Andrew tapers off from the mental health medications his father had prescribed for him most of his life, he begins to emerge from his emotionless shell. This leads him to reconnect with his childhood friends and start a relationship with a quirky young woman named Sam (Natalie Portman).

There is an understated beauty that permeates throughout "Garden State," finding serenity amidst all the overt melancholia. Throughout the movie, Andrew not only reconnects with himself but also learns to appreciate life, particularly through his romantic relationship with Sam. This is powered by a solid indie rock original soundtrack and the movie's quietly evocative cinematography. One of the best things Braff was ever involved in, and his best feature film project, "Garden State" is a fantastic coming-of-age movie for the emo crowd.

While Jason Segel may be best known for his extensive work in television comedies, he made a splash in 2008 starring in and writing the romantic comedy "Forgetting Sarah Marshall." Segel plays Peter Bretter, a television music composer who is dumped by his famous actor girlfriend Sarah Marshall (Kristen Bell). Deciding to clear his mind with a Hawaiian vacation, Peter is shocked when Sarah and her new boyfriend, rocker Aldous Snow (Russell Brand), are staying in the bungalow next door. As Peter struggles to move on, he strikes up a romance with the resort's concierge Rachel Jansen (Mila Kunis).

Right from its hilariously awkward opening break-up scene, it's clear that "Forgetting Sarah Marshall" has no qualms with letting it all hang out (and impressing Harrison Ford in the process). Segel is sweetly innocent and vulnerable all at once, often in service to the movie's biggest laughs. Along the way, Peter undergoes a quiet arc of discovering his own self-worth and recognizing the toxicity of his past relationship. An enduring comedy of navigating messy break-ups and new love, "Forgetting Sarah Marshall" is among Segel's best work.

Real-life couple Paul Dano and Zoe Kazan are at the center of the 2012 fantasy romantic dramedy "Ruby Sparks," which Kazan also wrote. Dano plays introverted and struggling young novelist Calvin Weir-Fields, who writes about his idealized romantic partner, naming his fictional creation Ruby Sparks. Calvin is shocked by Ruby apparently coming to life and happily joining him, with Calvin unsure how to proceed with writing her, knowing it unconsciously affects her personality. This leads to greater questions about consent and agency as friction develops between Calvin and Ruby as she grows beyond what he had originally envisioned and controlled.

Though the messaging about control and coercion within a relationship is serious business, the tone throughout "Ruby Sparks" remains relatively light-hearted. Kazan's screenplay is sharply written and she and Dano clearly play well off of each other, with Dano giving one of his best performances. And the supporting cast around the two leads helps buoy the fantastical concept, informing the malaise that forms between the core couple and their unique dynamic. Imaginative and smartly staged, "Ruby Sparks" deconstructs the concept of an idealized romantic partner and its implications.

A love letter to jazz and classic Hollywood musicals, "La La Land" features the fan-favorite pairing of Ryan Gosling and Emma Stone. Gosling plays talented pianist Seb Wilder, who dreams of opening his own jazz club, while Stone plays aspiring actor Mia Dolan, with dreams of silver screen success. Despite initially being at odds, the couple forms a tentative romance while they each progress with their respective entertainment industry careers. However, as both of their dreams begin to take shape, with accompanying pressures, Seb and Mia's budding relationship comes under intense strain.

Filmmaker Damien Chazelle, who wrote and directed "La La Land," stages the 2016 film with all the show-stopping aplomb as the movie musicals that inspired it. The dance sequences are energetically choreographed while the cinematography captures the beauty and elegance of Los Angeles in colorful ways. And, of course, the chemistry between Gosling and Stone is as electric as ever, with this project arguably their strongest collaboration to date. Unapologetically old school without feeling dated, "La La Land" remains Chazelle's gorgeously realized magnum opus.