5 Movies Like The Wedding Singer (1998)

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

Plenty of films have been made about the grueling climb to rock-and-roll fame, but few carry the effortless charm that That Thing You Do! has. Written and directed by Tom Hanks, the film is as cookie-cutter as it gets, dodging the dark depths that typically haunt rock biopics. But that isn’t to say That Thing You Do! is boring—just the opposite, its simplicity and nostalgia make it wholly enjoyable. It’s a confection of a film that goes down easy, and it will have you smiling and bopping your head from start to end.

Genre: Comedy, Drama, Music, Romance

Actor: Alex Rocco, Barry Sobel, Benjamin John Parrillo, Bill Cobbs, Brittney Powell, Bryan Cranston, Charlize Theron, Chris Ellis, Chris Isaak, Claudia Stedelin, Clint Howard, Clive Rosengren, Colin Hanks, Dawn Maxey, Elizabeth Hanks, Erika Greene, Ethan Embry, Gedde Watanabe, Gina Aponte, Giovanni Ribisi, Heather Hewitt, Holmes Osborne, Johnathon Schaech, Jonathan Demme, Kathleen Kinmont, Keith Neubert, Kevin Pollak, Lee Everett, Liv Tyler, Marc McClure, Mars Callahan, Michael P. Byrne, Obba Babatundé, Paul Feig, Peter Scolari, Renée Lippin, Rita Wilson, Robert Ridgely, Robert Torti, Robert Wisdom, Sarah Koskoff, Sean Whalen, Steve Zahn, Tom Everett Scott, Tom Hanks, Tracy Reiner, Warren Berlinger

Director: Tom Hanks

Rating: PG

Before “burnout,” “bullshit jobs,” and “quiet quitting” became part of our everyday lexicon, there was a film in the ‘90s that prophesied the rise of these workplace problems. Office Space follows three co-workers who, having had enough of their dreary low-paying jobs, fight back against their company via an embezzlement scheme. 

Office Space makes the most out of its indie budget as it mostly takes place in the cramped quarters of a company, effectively bottling us into the cubicled windowless world of the characters. But the real beauty of the film is in the details, from its quick zingers and thoughtful takes on the essence of work down to its elaborate “planning to plan” scheme in the background and the employees’ forced politeness singing happy birthday to their boss. Modern viewers will notice that Office Space sits right in between the dystopian thriller Severance and the beloved sitcom The Office—a dark comedy that highlights the necessity of humanity in everyday work. 

Genre: Comedy, Drama

Actor: Ajay Naidu, Alexandra Wentworth, Ali Wentworth, Barbara George-Reiss, Cassie Townsend, Charissa Allen, David Herman, Diedrich Bader, Gabriel Folse, Gary Cole, Greg Pitts, Heath Young, Jack Betts, Jackie Belvin, Jennifer Aniston, Jennifer Jane Emerson, Jesse De Luna, Joe Bays, John C. McGinley, Josh Bond, Justin Possenti, K. Todd Lytle, Kinna McInroe, Kyle Scott Jackson, Linda Wakeman, Michael McShane, Mike Judge, Orlando Jones, Paul Willson, R.C. Keene, Richard Riehle, Ron Livingston, Rupert Reyes, Samantha Inoue Harte, Spencer Kayden, Stephen Root, Todd Duffey, Tom Schuster

Director: Mike Judge

Rating: R

When David and his sister Jennifer fight over the TV remote, they are suddenly transported to David’s favorite sitcom, Pleasantville. They’re told by a spirit guide that their best bet at getting out is fitting in, but their modern sensibilities prove to be too much for the genteel ‘50s town. Soon, the residents learn about sex, art, criticism, and politics, and it’s up to the twins to control the ensuing mayhem and guide them to the right path. 

In hindsight, Pleasantville seems ahead of its time, preceding Marvel’s WandaVision as the ultimate, deconstructed homage to 20th-century television. But unlike the series, Pleasantville dives deep into personal and social politics, all while maintaining an impressive balance of wisdom and humor. Equally notable is the film’s transformation from black and white to Technicolor, which, aside from being a symbolic and technical feat, is also a piece of pure, mesmerizing cinema.

Genre: Comedy, Drama, Family, Fantasy

Actor: Andrea Baker, Charles C. Stevenson Jr., Danny Strong, David Tom, Dawn Cody, Denise Dowse, Don Knotts, Erik MacArthur, Gerald Emerick, Giuseppe Andrews, J. Patrick Lawlor, J.T. Walsh, James Keane, Jane Kaczmarek, Jason Behr, Jason Maves, Jeanine Jackson, Jeff Daniels, Jenny Lewis, Jim Antonio, Joan Allen, John Ganun, Johnny Moran, Justin Nimmo, Kai Lennox, Kevin Connors, Kristin Rudrüd, Laura Carney, Lela Ivey, Maggie Lawson, Marc Blucas, Marissa Ribisi, Marley Shelton, McNally Sagal, Nancy Lenehan, Natalie Ramsey, Patrick Thomas O'Brien, Paul Morgan Stetler, Paul Walker, Reese Witherspoon, Robin Bissell, Stanton Rutledge, Tobey Maguire, Weston Blakesley, William H. Macy

Director: Gary Ross

Rating: PG-13