20 Must-Watch Movies If You Feel Lost in Your 20s

Singles (1992)

Ah, the ‘90s – when flannel was fashion, grunge was gospel, and Seattle was the center of the universe. Singles drops you right into that era, following a group of twenty-somethings as they navigate love, heartbreak, and the struggle to make rent while chasing their dreams. Directed by Cameron Crowe, this rom-com features Bridget Fonda, Campbell Scott, and Matt Dillon, who brings his signature cool-guy energy as a wannabe rock star. Oh, and did we mention that Pearl Jam and Soundgarden make appearances? If you’ve ever been confused about relationships, careers, or whether your crush will ever call back, this film understands you. Plus, it’ll leave you wanting to blast some ‘90s alt-rock and maybe even move to Seattle. | © Warner Bros.

Dazed and Confused (1993)

Alright, alright, alright! Before Matthew McConaughey was an Oscar-winning actor, he was Wooderson – the smooth-talking, high-school-graduated guy who just couldn’t let go of the past. Dazed and Confused is less of a movie and more of a vibe, capturing the last day of school in 1976 with a cast that includes Ben Affleck (as the world’s worst bully), Milla Jovovich, and Parker Posey. It’s all about teenage rebellion, aimless wandering, and the realization that adulthood is coming whether you’re ready or not. If you’ve ever felt like life is just one long, slightly chaotic road trip with no clear destination, this film gets you. Bonus points if you watch it while lying on your couch, contemplating your existence. | © Gramercy Pictures

Reality Bites (1994)

Feeling like a broke, underemployed, existentially confused post-grad? Reality Bites might just be your life story. Winona Ryder stars as an aspiring filmmaker stuck in a cycle of bad job interviews, awkward dates, and deep philosophical discussions with her equally lost friends – played by Ethan Hawke, Janeane Garofalo, and Steve Zahn. Directed by Ben Stiller (who also co-stars as a buttoned-up yuppie), the movie perfectly captures that messy, in-between phase where you're too old for college but not quite "adult" enough for the real world. It’s funny, it’s angsty, and it features an all-too-relatable love triangle that makes you want to scream at the screen. Watch this if you need reassurance that no one really has it all figured out – especially in their 20s. | © Universal Pictures

Before Sunrise (1995)

Imagine you meet a ridiculously attractive stranger on a train, and instead of doom-scrolling your phone or pretending to be asleep, you actually talk to them. That’s Before Sunrise in a nutshell. Ethan Hawke (again – he really was the ‘90s poster boy for existential crises) and Julie Delpy play Jesse and Céline, two young wanderers who decide to spend an entire night exploring Vienna, talking about love, life, and all those deep thoughts you only share at 2 AM. Directed by Richard Linklater, this movie is basically one long, beautiful conversation that makes you believe in the magic of chance encounters. If you’ve ever dreamed of dropping everything for an unexpected adventure, this one’s for you. Just don’t blame me if you suddenly feel the urge to book a train ticket to Europe. | © Warner Bros.

Good Will Hunting (1997)

What if you were secretly a genius but preferred spending your nights at dive bars rather than libraries? That’s the dilemma of Will Hunting, played by a young, scruffy-haired Matt Damon in this heartfelt drama. Alongside his real-life bestie Ben Affleck, and the legendary Robin Williams as a therapist who hits you with the kind of wisdom that’ll leave you in tears, this movie is about overcoming your fears, embracing your potential, and realizing that it’s okay to ask for help. It also features one of the greatest “friendship pep talk” scenes in cinematic history. If you’re feeling stuck in your 20s, unsure of where life is taking you, Good Will Hunting is a gentle but firm reminder: you’re not alone, and yeah, it’s not your fault. | © Miramax Films

Almost Famous (2000)

Ever dreamed of dropping everything and going on tour with a rock band? Well, Almost Famous is your ultimate fantasy (minus the stress of actually writing deadlines). Directed by Cameron Crowe, this coming-of-age gem follows a 15-year-old aspiring journalist (played by Patrick Fugit) who gets the chance of a lifetime to tour with a band and write for Rolling Stone. Along the way, he meets the effortlessly cool Penny Lane, played by Kate Hudson, and learns that adulthood is basically just faking confidence until you make it. With Billy Crudup as the brooding rockstar and Frances McDormand as the overprotective mom, this film is a love letter to music, youth, and figuring yourself out on the road. Warning: May cause a sudden urge to buy vinyl records and wear vintage band tees unironically. | © DreamWorks Pictures

Ghost World (2001)

Feeling like an outsider who just doesn’t vibe with mainstream society? Welcome to Ghost World, where sarcasm is a survival skill and the future is an open-ended question you’d rather not answer. Thora Birch and Scarlett Johansson play Enid and Rebecca, two cynical best friends who are trying to navigate post-high school life – aka working dead-end jobs and judging everyone in sight. When Enid gets entangled with an oddball record collector (Steve Buscemi at his most awkwardly endearing), things get even more complicated. It’s quirky, dry, and painfully relatable for anyone who’s ever felt like they don’t quite fit in. If you’re currently side-eyeing society and questioning your life choices, congratulations, this movie was made for you. | © United Artists

Lost in Translation (2003)

Ever felt completely out of place, even when you’re surrounded by people? That’s Lost in Translation in a nutshell. Sofia Coppola’s dreamy, melancholic masterpiece follows two lonely souls – played by Bill Murray and a young Scarlett Johansson – who find an unexpected connection while adrift in Tokyo. He’s an aging actor questioning his career; she’s a recent college grad wondering what’s next. Together, they share late-night conversations, neon-lit adventures, and that one iconic whisper that still haunts the internet. This movie is less about plot and more about vibes, making it perfect for those existential “what am I even doing with my life?” moments. Pro tip: Watch it with a warm drink and a soft blanket. Existential dread just hits different that way. | © Focus Features

Cropped Eternal Sunshine of the Spotless Mind

Eternal Sunshine of the Spotless Mind (2004)

Imagine if you could erase all memories of your worst heartbreak. Tempting, right? Well, Eternal Sunshine of the Spotless Mind explores exactly that, but with a gut-punching dose of reality. Jim Carrey ditches his usual goofy antics to play Joel, a heartbroken guy who undergoes a procedure to forget his ex, Clementine (played by a wonderfully chaotic Kate Winslet). But memories aren’t so easy to erase, and as Joel relives their relationship in reverse, he realizes that maybe love even the painful parts – is worth holding onto. Directed by Michel Gondry and written by Charlie Kaufman (so, yeah, expect mind-bending visuals and deep emotional turmoil), this film will make you rethink love, fate, and whether forgetting is ever the answer. Warning: May cause an existential spiral. Proceed with caution. | © Focus Features

Garden State (2004)

If you’ve ever returned to your hometown and felt like you were walking through a weird, nostalgia-fueled dream, then Garden State will hit home. Written, directed by, and starring Zach Braff (aka J.D. from Scrubs), this indie classic follows Andrew, a struggling actor who comes back for his mother’s funeral and ends up on a soul-searching journey – complete with awkward reunions, deep conversations, and a manic pixie dream girl (Natalie Portman) who changes everything. Featuring a killer soundtrack (yes, The Shins scene is still iconic), this movie is like a warm, slightly melancholic hug for anyone feeling adrift in their 20s. Watch it if you need a reminder that sometimes, the weirdest detours lead to the best realizations. | © Fox Searchlight Pictures

Waiting... (2005)

Ever worked in food service and seriously questioned your life choices? Then Waiting... is basically a documentary. This raunchy workplace comedy follows a group of restaurant employees at Shenaniganz (yes, that’s the actual name) as they kill time between terrible customers, questionable kitchen hygiene, and soul-crushing shifts. Ryan Reynolds leads the way with his signature sarcastic charm, while Justin Long plays the guy who realizes he might be stuck in this dead-end job forever. With Anna Faris, Luis Guzmán, and Dane Cook (yep, this was peak 2000s), this movie is a hilarious, slightly horrifying look at the chaos of working in the service industry. If you’ve ever faked enthusiasm for tips or plotted your escape from a minimum-wage nightmare, this one will hit way too close to home. | © Lionsgate Films

The Squid and the Whale (2005)

If your childhood included watching your parents’ marriage crumble in real-time while you developed a deep appreciation for sarcasm, The Squid and the Whale will feel oddly familiar. This indie drama, directed by Noah Baumbach, explores the fallout of divorce through the eyes of two teenage brothers played by Jesse Eisenberg and Owen Kline. Their parents – Jeff Daniels as the pretentious, washed-up writer and Laura Linney as the mother who’s done with his nonsense – turn co-parenting into an emotional battleground. It’s dark, awkwardly funny, and painfully honest, making it perfect for anyone still unpacking their family’s dysfunction. Bonus points if you, too, pretended to have read The Metamorphosis just to sound intellectual. | © Sony Pictures Classics

Adventureland (2009)

First jobs are never glamorous, but working at a rundown amusement park in the ‘80s? That’s a whole new level of disillusionment. Adventureland follows Jesse Eisenberg (in peak awkward, overthinking mode) as he takes a summer gig that turns out to be less about earning money and more about life lessons, bad decisions, and falling for Kristen Stewart’s effortlessly cool yet emotionally unavailable character. Also starring Ryan Reynolds as the washed-up dude who never left town, and Bill Hader and Kristen Wiig as the delightfully weird park managers, this movie perfectly captures that weird transitional phase where you’re technically an adult but still have no idea what you're doing. Watch this if you need reassurance that even the worst jobs come with a good story (or at least free funnel cake). | © Miramax Films

Frances Ha (2012)

Have you ever felt like your life is one long, chaotic episode of "figure it out as you go"? Meet Frances, played by Greta Gerwig in the role that solidified her as the queen of millennial existentialism. This black-and-white indie darling follows Frances, a 27-year-old aspiring dancer who is definitely not where she thought she’d be at this stage in life. She couch-surfs, struggles financially, and watches her best friend (played by Mickey Sumner) move on to a more stable, adult-ish existence. Directed by Noah Baumbach, this movie is charming, cringeworthy, and painfully relatable for anyone who has ever pretended to have it all together while secretly spiraling. Watch it if you need reassurance that flailing around in your 20s is actually pretty normal. | © IFC Films

The Perks of Being a Wallflower (2012)

If you were ever the quiet kid who felt more comfortable in books than in social settings, The Perks of Being a Wallflower will hit you right in the feelings. Based on the beloved novel by Stephen Chbosky, this coming-of-age film follows Charlie (Logan Lerman), a shy high school freshman who finds himself taken under the wing of two charismatic seniors – Emma Watson as the effortlessly cool Sam and Ezra Miller as the wonderfully eccentric Patrick. With a killer soundtrack and heart-wrenching themes of mental health, trauma, and friendship, this movie is a beautiful, sometimes painful reminder that even the most lost souls can find their people. Plus, it gave us one of the most iconic lines in modern cinema: “We accept the love we think we deserve.” If that doesn’t send you into a full-on existential spiral, are you even in your 20s? | © Summit Entertainment

Inside Llewyn Davis (2013)

If you've ever felt like the universe is actively conspiring against your success, Inside Llewyn Davis will feel painfully familiar. Directed by the Coen Brothers, this melancholy yet darkly funny film follows Llewyn Davis (played by Oscar Isaac, brooding his way through every scene), a struggling folk musician in 1960s New York. He’s talented, sure, but life just won’t give him a break – he’s broke, homeless, and carrying around a cat that isn’t even his. The movie also features a pre-Star Wars Adam Driver in a hilariously weird singing role, Carey Mulligan as a fed-up ex, and Justin Timberlake as, well, a much more successful musician. If you’ve ever felt like you're screaming into the void while watching less talented people thrive, this movie understands your pain. Just don’t expect a happy ending – it’s the Coen Brothers, after all. | © CBS Films

Lady Bird (2017)

Ah, the teenage years – the era of big dreams, questionable fashion choices, and aggressively arguing with your mom about literally everything. Lady Bird, directed by Greta Gerwig, is a love letter to that awkward transition from high school to adulthood. Saoirse Ronan plays Christine "Lady Bird" McPherson, a quirky, stubborn teen who’s desperate to escape her Sacramento hometown and make it to an East Coast college (even if her grades say otherwise). Meanwhile, Laurie Metcalf delivers an all-too-relatable performance as her mother, whose tough love is equal parts frustrating and deeply moving. Throw in Timothée Chalamet as a pseudo-intellectual bad boy and Lucas Hedges as an emotional wreck, and you’ve got a coming-of-age masterpiece. Whether you’re navigating the chaos of your early 20s or just reminiscing about your dramatic teenage years, this film gets you. | © A24

Shiva Baby (2020)

Have you ever been trapped in a social event where everyone is asking intrusive questions about your life, and your anxiety is skyrocketing by the second? Then Shiva Baby is your worst nightmare – wrapped in dark comedy brilliance. Directed by Emma Seligman, the movie follows Danielle (Rachel Sennott, in peak overwhelmed millennial mode) as she attends a Jewish shiva (a post-funeral gathering) only to run into her ex-girlfriend, her overbearing parents, and – plot twist – her sugar daddy and his wife. It’s tense, hilarious, and so painfully relatable that you might need to take deep breaths while watching. Featuring a scene-stealing performance by Molly Gordon, this film is basically an anxiety attack in movie form, but like… in a good way? | © Utopia

The Half of It (2020)

High school romance movies are a dime a dozen, but The Half of It flips the script in the best way. Directed by Alice Wu, this heartfelt coming-of-age story follows Ellie Chu (Leah Lewis), a shy, brainy girl who makes extra cash by writing essays for her classmates. When she’s asked to write love letters for a clueless jock (Daniel Diemer) to help him woo the effortlessly cool Aster (Alexxis Lemire), things get complicated – because Ellie also has a crush on Aster. Cue the heartfelt, messy, and deeply relatable journey of self-discovery. With stunning cinematography and a refreshingly tender take on identity and first love, this movie is perfect for anyone who’s ever felt like they’re playing a supporting role in their own love story. | © Netflix

The Worst Person in the World (2021)

If you’ve ever had an existential crisis while scrolling through social media, wondering if you’re completely screwing up your life, congratulations – you’re the target audience for The Worst Person in the World. This Norwegian dramedy, directed by Joachim Trier, follows Julie (Renate Reinsve, who won Best Actress at Cannes for this), a 30-something who keeps changing careers, relationships, and life plans like she’s cycling through Netflix recommendations. She’s smart, funny, flawed, and – let’s be honest – uncomfortably relatable. Whether she’s running through the streets of Oslo in a surreal romantic high or having painfully real conversations about commitment and purpose, Julie is all of us at some point. This movie will make you laugh, cry, and question every decision you’ve ever made – so, you know, the usual 20s experience. | © Neon