10 Movies Like Clueless (1995)

Staff & contributors

Written and directed by Academy-Award-winning Kenneth Lonergan (Manchester by the Sea, Gangs of New York), you can certainly count on the qualities of this subtle, beautiful, and moving drama about two siblings growing apart and reuniting later in life.

An Academy-Award-nominated Laura Linney plays Sammy, a single mother in a small town who is extremely protective of her 8-year-old son. When her younger and somewhat troubled brother Terry (played by the ever-reliable Mark Ruffalo) visits her out of the blue, Sammy has to deal with a slew of contradicting emotions towards her brother, whose appearance threatens to upend her life as she knew it.

Straight, thoughtful, and beautifully crafted, You Can Count on Me is an honest and genuine exploration of unconditional love in celluloid form. Think of it as much more hopeful The Skeleton Twins.

Genre: Drama, Family

Actor: Adam LeFevre, Amy Ryan, Betsy Aidem, Gaby Hoffmann, Halley Feiffer, J. Smith-Cameron, Jon Tenney, Josh Lucas, Kenneth Lonergan, Laura Linney, Lisa Altomare, Mark Ruffalo, Matthew Broderick, Michael Countryman, Nina Garbiras, Rory Culkin, Whitney Vance

Director: Kenneth Lonergan

Rating: R

A seven year old Bryce (Callan McAuliffe) moves to a new neighbourhood across the street from a very spirited little girl named Juli (Madeline Carroll). She falls in love at first sight much to the dismay of the shy young lad. For the next six years, Juli overwhelms Bryce with her affections until a series of events and misunderstandings leaves her heartbroken and angry at him. Fed up, Juli begins to ignore him. However, her absence triggers a change of heart as Bryce realizes his fondness of her. He will do anything to win her back. The whole film, set in the late fifties holds the warmth and charm of small town living. With a balance of passion and playfulness, the extraordinary young cast are brilliant in their roles. Based on the novel by Wendelin Van Draanen, this endearing story of young puppy love, will make your heart melt!

Genre: Comedy, Drama, Romance

Actor: Aidan Quinn, Anthony Edwards, Ashley Taylor, Callan McAuliffe, Cody H. Carolin, Cody Horn, Inga R. Wilson, Israel Broussard, John Mahoney, Kevin Weisman, Madeline Carroll, Matthew Gold, Michael Bolten, Morgan Lily, Patricia Lentz, Penelope Ann Miller, Rebecca De Mornay, Ryan Ketzner, Shane Harper, Stefanie Scott, Wallace Bridges

Director: Rob Reiner

Rating: PG

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

From a 1926 play to the iconic 1975 stage musical to Rob Marshall's 2002 extravaganza, Chicag0 has had a strong hold on popular culture. In a way, it's existed almost as long as cinema itself and its transformation across mediums and modes of expression has been well documented. The film carries all the marks of its theatrical predecessors, the expansive sets, the luscious costumes, the sleek characters whose banter and songs alike testify to their great chemistry — there's a lot to admire in such a self-referential spectacle. A black-comedy-fuelled musical about corruption and deceit set during the Jazz Age, Chicago fulfils all its promises. With a stellar ensemble cast featuring Renée Zellweger, Catherine Zeta-Jones, Richard Gere, and John C. Reily, in tandem with dazzling camerawork and most exquisite chiaroscuro lighting, this one brings the stage to the movies. I mean it in the best possible way!

Genre: Comedy, Crime, Drama

Actor: Bill Corsair, Blake McGrath, Brendan Wall, Brittany Gray, Bruce Beaton, Capathia Jenkins, Catherine Chiarelli, Catherine Zeta-Jones, Chita Rivera, Christine Baranski, Cliff Saunders, Colm Feore, Conrad Dunn, Cynthia Onrubia, Danielle Rueda-Watts, Darren Lee, Deidre Goodwin, Deirdre Goodwin, Denise Faye, Dominic West, Ekaterina Chtchelkanova, Eve Crawford, Faye Rauw, Gregory Mitchell, Jayne Eastwood, Jeff Clarke, Jeff Pustil, John C. Reilly, Jonathan Whittaker, Joseph Scoren, Karen Holness, Karine Plantadit, Kathryn Zenna, Ken Ard, Laura Dean, Lucy Liu, Marty Moreau, Michelle Johnston, Monique Ganderton, Mya, Nicki Richards, Paul Becker, Queen Latifah, Rebecca Leonard, Renée Zellweger, Rhonda Roberts, Richard Gere, Rick Negron, Rob Smith, Robbie Rox, Robert Montano, Roman Podhora, Roxane Barlow, Sara Ramirez, Sean McCann, Sean Palmer, Sebastian La Cause, Sergio Trujillo, Sheri Godfrey, Steve Behal, Susan Misner, Tara Nicole Hughes, Taye Diggs, Timothy Shew, Troy P. Liddell, Vicky Lambert

Director: Rob Marshall

Rating: PG-13

Spike Lee’s semi-autobiographical film is a loving and nostalgic ode to the Brooklyn of his childhood. It also happens to be his sweetest work and while overshadowed by the explosive Do The Right Thing, remains an easy contender for one of his very best. The world of Crooklyn is told through the eyes of Troy, a young girl growing up with her four brothers, and her mother and father in a cramped brownstone. 

Lee’s Brooklyn is a colorful delight set aloft by a swooning soul soundtrack. His ability to capture the vibrant magical tones and textures of the city feels as complete as ever, and marvelous performances from Alfre Woodard and Delroy Lindo as Troy’s parents help create a touching and all-encompassing experience. 

Genre: Comedy, Drama

Actor: Alfre Woodard, Arthur French, Bokeem Woodbine, Carlton Williams, Carmen Tillery, Christopher Knowings, Christopher Wynkoop, Dan Grimaldi, Danielle K. Thomas, David Patrick Kelly, Delroy Lindo, Emelise Aleandri, Frances Foster, Gary Perez, Harvey Williams, Hector M. Ricci Jr., Isaiah Washington, Ivelka Reyes, Joie Lee, José Zúñiga, Keith Johnson, Kewanna Bonaparte, Manny Perez, Maurie A. Chandler, Michele Shay, Mildred Clinton, Norman Matlock, Omar Scroggins, Patriece Nelson, Peewee Love, Raymond Reliford, Rene Ojeda, Richard Whiten, RuPaul, Sharif Rashed, Spike Lee, Taneal Royal, Tiasha Reyes, Tracy Vilar, Tse-Mach Washington, Ulysses Terrero, Vondie Curtis-Hall, Zelda Harris

Director: Spike Lee

The secret weapon to this charming story of a cranky, aging father and his new robot companion is the near-total dryness of its humor. On paper, this might sound like a depressing movie, but thanks to director Jake Schreier's sensitive touch, its protagonist's fading memory and family drama takes on the spark of youth once more. It's sweet and low-stakes, with most of the tension not coming from any fear that Frank might get caught in his hijinks, but in the curiosity of seeing if he can get back to his thieving roots. A great cast including Frank Langella, James Marsden, and Jeremy Strong keep every emotion coming consistently.

Genre: Comedy, Crime, Drama, Science Fiction

Actor: Ana Gasteyer, Bonnie Bentley, Dana Morgan, Dario Barosso, Frank Langella, James Marsden, Jeremy Sisto, Jeremy Strong, Jesse Newman, Joshua Ormond, Katherine Waterston, Liv Tyler, Peter Sarsgaard, Rachael Ma, Susan Sarandon

Director: Jake Schreier

It’s easy enough to pitch Moonstruck with the promise of Cher and a young Nicolas Cage getting hot and heavy in 80s New York, but it’s so much more than its two outsized leads. Loretta (Cher) is on track to marry Johnny (Danny Aiello) when he tasks her with inviting his brother Ronny (Nicolas Cage) to their wedding. Before long Loretta and Ronny are having a whirlwind affair that threatens to derail everything. 

Despite the somewhat risque premise, Moonstruck is a lighthearted, sentimental, romance fit for the holidays. A big cast playing the warm-hearted family rounds things out, and some of the best moments are digressions that explore the romantic entanglements outside of the central couple.  At times Moonstruck feels a bit too big, too over-the-top, too cheesy, but it’s a New York slice cheesy, it’s a ‘That’s Amore’ cheesy, it’s a cheesy that tucks you in at night after a  helping of manicotti and a big bottle of wine.

Genre: Comedy, Drama, Romance

Actor: Al Therrien, Amy Aquino, Anita Gillette, Ann McDonough, Antonia Minella, Betty Orsatti, Catherine Scorsese, Cathy Ladman, Charles Scorsese, Cher, Curt Hayward, Cynthia Dale, Danny Aiello, David Hummel, David S. Howard, Feodor Chaliapin Jr., Frank Gio, Gina DeAngeles, Helen Hanft, Helen Proimos, Joe Grifasi, John Christopher Jones, John Mahoney, Julie Bovasso, Leonardo Cimino, Lisa Howard, Lou Pitoscia, Louis Di Bianco, Louis Guss, Matt Myers, Mimi Cecchini, Mimi Lizio, Nada Despotovich, Nicholas Pasco, Nicolas Cage, Olympia Dukakis, Paul Benedict, Paula Trueman, Peter Austin Noto, Robert Weil, Robin Bartlett, Sonny Bono, Stephany Hitchcock, Tim Koetting, Tommy Hollis, Tony Azito, Vincent Gardenia

Director: Norman Jewison

Though it starts off somewhat slow, I was delightfully surprised at how much I loved this movie. A 28-year-old man ventures through Europe with a buddy, ending in Copenhagen, where he hopes to contact the last of his family. There he enlists a local girl to help him. An interesting relationship unfolds as they take a captivating journey through Copenhagen in search of William’s grandfather. The tag line of the movie is “When the girl of your dreams is half your age, it’s time to grow up” and William really does have to grow up when he’s faced with his own personal tumult. The girl is played by Frederikke Dahl Hansen, who gives an exceptional natural performance, which adds even more to the abundance of charm in this film.

Genre: Adventure, Drama, Romance

Actor: Asbjørn Krogh Nissen, Baard Owe, Christian Brandt, Frederikke Dahl Hansen, Gethin Anthony, Gordon Kennedy, Hélène Kuhn, Martin Hestbæk, Martin Hestbæk, Mille Dinesen, Olivia Grant, Sebastian Armesto, Sebastian Bull Sarning, Silja Eriksen Jensen, Tamzin Merchant, Zaki Nobel Mehabil

Director: Mark Raso

Rating: Not Rated, Unrated

A happy-go-lucky couple who are expecting their first child travel around the U.S. in order to find a perfect place to start their family. Along the way, they have misadventures and find fresh connections with an assortment of relatives and old friends who just might help them discover "home" on their own terms for the first time. Starring Jon Krasiniski and Maya Rudolph, and partially written by Dave Eggers, this film hits all the sentimental buttons without being cloying or trite.

Genre: Comedy, Drama, Romance

Actor: Allison Janney, Carmen Ejogo, Catherine O'Hara, Chris Messina, Conor Carroll, Jeff Daniels, Jim Gaffigan, John Krasinski, Josh Hamilton, Maggie Gyllenhaal, Maya Rudolph, Melanie Lynskey, Paul Schneider

Director: Sam Mendes

If you’ve ever been puzzled by “Greek life”, this documentary will go some way to demystifying that somewhat baffling phenomenon of American college culture. Bama Rush follows four hopefuls as they “rush” the University of Alabama’s sororities, a TikTok-viral weeklong recruitment process so cutthroat some candidates spend months preparing for it. The documentary digs deep into why these young women put so much time, energy, and money into joining what the film hints is a largely unforgiving and reductive element of campus life. What it finds is pretty affecting: they’re really just looking for acceptance and belonging.

Threaded throughout are director Rachel Fleit’s reflections on her own history with those motivations, having grown up with alopecia. Though it does illustrate that rushing isn’t so dissimilar from other quests for acceptance, this parallel is sometimes clunkily drawn — and can seem somewhat self-indulgent in places, given the documentary’s comparatively surface-level exploration of more systemic issues. A late development shifts Bama Rush into an even deeper self-reflexive mode, as the film itself becomes a contentious issue in the process it’s documenting. Despite its flaws, turns like this — and its participants’ extraordinary candor — help make Bama Rush an often illuminating look into an opaque world. 

Genre: Documentary, Drama

Director: Rachel Fleit