11 Movies Like Chasing Amy (1997)

Staff & contributors

Chasing the feel of watching Chasing Amy ? Here are the movies we recommend you watch right after.

For a film made in the mid-90s, by a straight white man in his early 20s, Chasing Amy is startingly smart and sensitive, filled with more relatable moments than anyone would care to admit. Sure, by today’s standards, its exploration of sexuality is questionable at best and cringe-worthy at worst, but it’s also an honest depiction of how an era (and some people still) confront this reality. And for all the important issues it tries to address, like homophobia, racism, and toxic masculinity, it’s also at its core a confectionary romcom. If When Harry Met Sally asks, “Can women and men be friends?”, then Chasing Amy complicates it with a question of its own: “Can a lesbian and a guy who falls in love too quickly be friends?” You may or may not arrive at an answer by the film’s end, but you’ll find much to like in its earnestness and thoughtfulness.

Starring Matthew Broderick and a young Reese Witherspoon as, respectively, Jim McAllister, a high school teacher and Tracy Flick, a notorious 'that girl' in his class. When Tracy decides to run for class president, we see the floodgates open as all sorts of bizarre and insane behavior pours out of the two. Quickly, it becomes clear that Tracy will do nearly anything to win, and as circumstances spiral out of control, madness descends - along with hilarity!

Genre: Comedy, Drama, Mystery, Romance

Actor: B.J. Tobin, Chris Klein, Colleen Camp, Delaney Driscoll, Frankie Ingrassia, Holmes Osborne, Jason Paige, Jeanine Jackson, Jessica Campbell, Jillian Crane, John Ponzio, Kaitlin Ferrell, Marilyn Tipp, Mark Harelik, Matt Golden, Matt Malloy, Matthew Broderick, Molly Hagan, Nicholas D'Agosto, Phil Reeves, Reese Witherspoon, Rohan Quine

Director: Alexander Payne

Rating: R

Strictly Ballroom is an energetic, fun and hilarious movie. Baz Lurhman does an incredible job telling the story of a rebellious young dancer who just wants to dance his own steps in the face of conformity. When he finds an inexperienced yet determined dance partner it's the beginning of an unexpected love story like no other. This movie isn't like the usual rom-com, it has colour, vitality and passion. It's a Moulin Rouge but with even more character, and the work that put Lurhman on the map for everyone.

Genre: Comedy, Drama, Romance

Actor: Antonio Vargas, Armonia Benedito, Barry Otto, Bill Hunter, Gia Carides, John Hannan, Kris McQuade, Lauren Hewett, Pat Thomson, Paul Bertram, Paul Mercurio, Peter Whitford, Pip Mushin, Sonia Kruger, Steve Grace, Tara Morice, Todd McKenney

Director: Baz Luhrmann, Baz Lurhman

Rating: PG

A marvelous combination of perfect casting and a sizzling script. William Hurt, Albert Brooks, and Holly Hunter are such natural talents they could make reading a dictionary watchable, but seeing them weave through James L Brooks punchy dialogue is a delight to behold. The three form the foundation of this drama that is as much about journalistic ambition as it is about love.

Hunter and Brooks are principled workaholics at a news station juggling a platonic friendship that seems destined for more but lacks a driving spark. Enter Hurt, a charming though self-admittedly stupid news anchor, who Hunter at once resents and yet can’t help falling for. What seems like a ready-built rom-com plot, however, churns into something else entirely. It’s a delicious film crackling with wit and character and is as funny as it is astute. 

Genre: Comedy, Drama, Romance

Actor: Albert Brooks, Amy Brooks, Christian Clemenson, Ed Wheeler, Frank Doubleday, Gennie James, Gerald F. Gough, Gerard Ender, Glen Roven, Holly Hunter, Jack Nicholson, Joan Cusack, John Cusack, Kimber Shoop, Leo Burmester, Lois Chiles, Luis Valderrama, Marc Shaiman, Marita Geraghty, Martha Smith, Nat Benchley, Peggy Pridemore, Peter Hackes, Raoul N. Rizik, Richard Thomsen, Robert Katims, Robert Prosky, Robert Walsh, Stephen Mendillo, William Hurt

Director: James L. Brooks

The '80s saw an influx of coming-of-age dramas, with John Hughes’ “Brat Pack” films reigning supreme. For better or worse, their most iconic scenes are embedded in pop culture, like students dancing in detention in The Breakfast Club or Sixteen Candles’ belated birthday cake. Perhaps the most iconic '80s movie moment comes not from Hughes, but from Cameron Crowe’s Say Anything…: Lloyd Dobler (John Cusak) in a trenchcoat, blue Malibu parked behind him, boombox raised over his head in defiant loyalty.

On their last day of high school, Lloyd Dobler resolves to ask out the class valedictorian Diane Court (Ione Skye). Their summer-long relationship is awkward, intense, tender—and familiar to anyone who has ever opened themselves up to falling in love. Say Anything… emotionally outclasses its contemporaries, as Crowe’s writing lends itself to two authentic characters fleshed out beyond caricatures. And as Lloyd crushes hard on Diane, it’s hard not to feel like you’re falling in love with each of them, too.

Genre: Comedy, Drama, Romance

Actor: Amy Brooks, Bebe Neuwirth, Bill Stevenson, Chynna Phillips, Dan Castellaneta, Don Wilson, Eric Stoltz, Glenn Walker Harris Jr., Gloria Cromwell, Gregory Sporleder, Ione Skye, Jason Gould, Jeremy Piven, Jerry Ziesmer, Jim Ladd, Joan Cusack, Joanna Frank, John Cusack, John Hillner, John Mahoney, Johnny Green, Jonathan Chapin, Judy Prescott, Kim Walker, Lili Taylor, Lisanne Falk, Lois Chiles, Loren Dean, Montrose Hagins, Pamela Adlon, Patrick O'Neill, Philip Baker Hall, Polly Platt, Richard Portnow, Stephen Shortridge, Stone Gossard

Director: Cameron Crowe

Of the many violence-inflected black comedies that Pulp Fiction spawned, Grosse Pointe Blank ranks among the best. Though it’s patently inspired by Tarantino’s magnum opus — John Cusack plays a sardonic, amoral hitman, and the film features bursts of stylized violence and a retro soundtrack — it never feels derivative. The film finds its own identity as a quirky romcom when Cusack’s character, Martin Blank, returns to his hometown for a 10-year high-school reunion on the advice of his terrified therapist (Alan Arkin).

Martin is experiencing professional disillusionment as part of the quarter-life crisis that often takes hold when one realizes it’s been a whole decade since high school. His profession puts a darkly comic spin on that convention, but the film doesn’t treat that element entirely flippantly. Unlike Martin — and so many of the film’s Pulp Fiction-inspired brethren — Grosse Pointe Blank isn’t nihilistic, but quite sincerely romantic. Its hybrid nature and surprising heart come to the fore in Martin’s renewed relationship with the girlfriend he jilted at prom: Debi (Minnie Driver), now a ska-loving radio DJ. Cusack and Driver have sparkling chemistry, which makes the sincerity with which their characters grapple with the possibility of a second chance at happiness all the more absorbing to watch.

Genre: Action, Comedy, Drama, Romance, Thriller

Actor: Alan Arkin, Ann Cusack, Barbara Harris, Belita Moreno, Benny Urquidez, Bill Cusack, Bobby Bass, Carlos Jacott, Dan Aykroyd, David Barrett, Doug Dearth, Hank Azaria, Jenna Elfman, Jeremy Piven, Joan Cusack, John Cusack, K. Todd Freeman, Michael Cudlitz, Minnie Driver, Mitchell Ryan, Steve Pink

Director: George Armitage

Peter Jackson made the transition from splattery gross-out movies like Braindead to more respectable fare with Heavenly Creatures, the true story of an intense relationship between two teenage girls that culminates in the murder of one of their mothers.

As the girls’ friendship becomes unhealthier, they invent a secret world for themselves, amusingly including a heart-throb Orson Welles. This gives Jackson the opportunity to indulge in his love of fantasy, creating some dazzling hallucinatory sequences.

The fantasy element contrasts beautifully with the humdrum setting of ‘50s New Zealand, and the final tragedy is heart-breaking. The film also provided an auspicious debut for Kate Winslet, who is terrific as one of the misguided fantasists.

Genre: Drama, Fantasy

Actor: Barry Thomson, Ben Fransham, Clive Merrison, Darien Takle, Diana Kent, Elizabeth Moody, Geoffrey Heath, Gilbert Goldie, Glen Drake, Glenys Lloyd-Smith, Jed Brophy, Jesse Griffin, Kate Winslet, Liz Mullane, Lou Dobson, Melanie Lynskey, Moreen Eason, Peter Elliott, Peter Jackson, Ray Henwood, Sarah Peirse

Director: Peter Jackson

Based on the comic book by Daniel Clowes, Ghost World is a dark comedy that follows the exploits of teenage outcasts Enid and Rebecca (Thora Birch and Scarlett Johansson) as they navigate the many complexities of burgeoning adulthood. Central to the story is the unlikely friendship that Enid strikes up with a lonesome older man (played by Steve Buscemi), a curious relationship that drifts through various humorous and melancholy situations. It’s an original and often poignant look at alienation and identity, with Birch delivering a wonderfully deadpan and often hilarious performance, despite her entirely pessimistic attitude. It’s the type of film that’s just right when you’re in the mood for something just a little bit different.

Genre: Comedy, Drama

Actor: Alex Solowitz, Anna Berger, Ashley Peldon, Bob Balaban, Brad Renfro, Brett Gilbert, Brian George, Brian Jacobs, Bruce Glover, Chachi Pittman, Charles C. Stevenson Jr., Charles Schneider, Daniel Graves, Danny Allen, Dave Sheridan, David Cross, Debi Derryberry, Debra Azar, Diane Salinger, Dylan Jones, Ezra Buzzington, Illeana Douglas, Jake La Botz, James Sie, Jerry Rector, Joan Blair, Joel Michaely, John Bunnell, Joseph Sikora, Joshua Wheeler, Joy Bisco, Kaileigh Brielle Martin, Lauren Bowles, Lindsey Girardot, Lorna Scott, Marc Vann, Martin Grey, Mary Bogue, Matt Doherty, Michelle McGinty, Pat Healy, Patrick Fischler, Paul Keith, Rini Bell, Scarlett Johansson, Sid Hillman, Stacey Travis, Steve Buscemi, T. J. Thyne, Teri Garr, Thora Birch, Tom McGowan, Tony Ketcham, Venus DeMilo Thomas, Will Forte

Director: Terry Zwigoff

Rating: R

Set in the 1930's English Countryside, the story of the eccentric Mortmain family is told from the daughter Cassandra's point of view. Her father, a once acclaimed and famous writer has written nothing in years, leading the family into bankruptcy. Themes such as first love and financial troubles are explored from Cassandra's comic and intelligent point of view. A classic and a must-see.

Genre: Drama, Romance

Actor: Alice Marie Crowe, Anna Paquin, Bijou Phillips, Bill Nighy, Billy Crudup, Christopher Ettridge, David Bamber, Dolly Wells, Eion Bailey, Eric Stonestreet, Fairuza Balk, Frances McDormand, Helena Little, Henry Cavill, Henry Thomas, James Faulkner, James Warrior, Jason Lee, Jay Baruchel, Jean Warren, Jimmy Fallon, Joe Sowerbutts, John Patrick Amedori, Kate Hudson, Kevin Sussman, Marc Blucas, Marc Maron, Michael Angarano, Noah Taylor, Patrick Fugit, Pauley Perrette, Philip Seymour Hoffman, Rainn Wilson, Ray Porter, Romola Garai, Rose Byrne, Sarah Woodward, Sinead Cusack, Sophie Stuckey, Tara Fitzgerald, Terry Chen, Zack Ward, Zooey Deschanel

Director: Cameron Crowe, Tim Fywell

Rating: R

Not enough movies tell the stories of the down-on-luck, kind of uncool wolf-pack that still goes out into town with their wallets on chains hanging from their pockets and try their luck with the ladies. Mike, heart-broken actor-comedian pines over his ex long after she's been gone, while his guys - Trent, Rob and Sue - try to help him get back in the game in a series of nights club-hopping and wingman-ing. You find yourself empathizing with Mike almost immediately if you've ever had a broken heart and root for him throughout his highs and fairly embarrassing lows. Sprinkled with clever references and subtle, refreshing humor, Mike's journey to find closure is more than likely to warm your heart.

As a bonus, the flawed yet endearing gang of twenty-something struggling actors will take you to that charming 90's nightlife in Los Angeles (with music to die for, by the way) and remind you that boys will be boys and that they're just doing their best helping each other and themselves to keep it together with lots of "You're so money, and you don't even know it!".

Genre: Comedy, Drama

Actor: Ahmed Ahmed, Alex Désert, Alex Désert, Bernard Serrano, Blake Lindsley, Brooke Langton, Curtis Lindersmith, Deena Martin, Heather Graham, Jan Dykstra, Jessica Buchman, Joan Favreau, Jon Favreau, Katherine Kendall, Kevin James Kelly, Maddie Corman, Martina Migenes, Molly Stern, Pamela Shaw, Patrick Van Horn, Rio Hackford, Ron Livingston, Samantha Lemole, Stephanie Ittleson, Stephen Gaghan, Vernon Vaughn, Vince Vaughn

Director: Doug Liman

Rating: R

Robert Duvall...Bill Murray...need I say more? This popped up in my Netflix feed as a suggestion. Almost skipped over it, but my husband and I were up late and took a chance. WHOA! The acting is superb and what we thought would be a movie about revenge is unexpectedly about redemption. Robert Duvall is a hermit, looking forward to death. Bill Murray is a funeral home director looking for someone to bury. It's subtle, very subtle, comical and heartbreaking. Y'all will love it.

Genre: Comedy, Drama, Mystery

Actor: Andrea Powell, Andy Stahl, Arin Logan, Bill Cobbs, Bill Murray, Blerim Destani, Chandler Riggs, Danny Vinson, Gerald McRaney, Linds Edwards, Lori Beth Sikes, Lucas Black, Marc Gowan, Robert Duvall, Scott Cooper, Sissy Spacek, Tomasz Karolak

Director: Aaron Schneider

Rating: PG-13

Chances are good you missed this movie the first time around due to the studio's big mishandling of it's promotion. The posters and trailers were squarely aimed at the lowbrow audience, ironically turning off the kind of viewers that would have appreciated the film. They promised an exploitation flick about an old black man keeping a sexy half-naked young white girl chained up in his shack. Which is, to be fair, exactly what you get - minus the exploitation. Samuel L. Jackson absolutely nails the role of Lazarus, a retired bluesman. He finds and rescues Rae (Christina Ricci) after she's left for dead in the road, and yeah, there's a chain, but.. well, you'll just have to see. Black Snake Moan is funny, sexy, tense, and (surprisingly) heartwarming. And oh hey by they way, its a helluva music-lovers' film in the bargain. Sporting a tremendous soundtrack full of that lowdown dirty blues (some performed by Jackson himself), you owe it to your ears to watch this someplace you have a decent sound system.

Genre: Drama

Actor: Adriane Lenox, Amy Lavere, Christina Ricci, Clare Grant, Claude Phillips, Cody Block, David Banner, David Chapman, Dhonna Harris Goodale, Jeff Pope, John Cothran, John Cothran, Jr., John Pickles, Justin Timberlake, Kim Richards, Leonard L. Thomas, Michael Raymond-James, Neimus K. Williams, S. Epatha Merkerson, Samuel L. Jackson, Willie Hall

Director: Craig Brewer

Rating: R