8 Movies Like Pleasantville (1998)

Staff & contributors

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

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.

Told through a series of flashbacks and personal archival footage, Beginners gives us the story of Oliver (Ewan McGregor), a 38-year-old graphic designer from Los Angeles, and his two parents across three timeframes. Oliver has never had a meaningful relationship. Six months after his mother dies, his father, Hal, played by the amazing, Academy Award-winning, and, sadly, late Christopher Plummer, comes out to Oliver. He lives the last days of his life in liberation and, well, gaiety, before protracting terminal cancer. Some months later, Oliver meets Anna at a party, a young French actress (Mélanie Laurent) who is beautiful and warm-hearted, and they start an affair. Through this all, there's Arthur, a Parson Jack Russell. But don't worry. He doesn't talk. Beginners is a beautiful and intricate film about finding love and happiness. It's funny, warm, and sincere. A beautiful movie.

Genre: Comedy, Drama, Romance

Actor: AlgeRita Wynn, Algerita Wynn Lewis, Amanda Payton, Bambadjan Bamba, Bruce French, Catherine McGoohan, China Shavers, Christopher Plummer, Cosmo, Ewan McGregor, Goran Visnjic, Jennifer Hasty, Joanna Trzepiecinska, Jodi Long, Jose Yenque, Kai Lennox, Keegan Boos, Lana Young, Lou Taylor Pucci, Luke Diliberto, Mélanie Laurent, Maria Semotiuk, Mary Page Keller, Mélanie Laurent, Melissa Tang, Michael Chieffo, Patrick Birkett, Patryk Wisniewski, Rafael J. Noble, Reynaldo Pacheco, Rodney Saulsberry, Terry Walters, Tymon Tymanski

Director: Mike Mills

Rating: N/A, R

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

Best in Show’s cast list reads like a catalog of comic greats. Among others, it includes Parker Posey, Jane Lynch, John Michael Higgins, Jennifer Coolidge, and the unbeatable duo that is Catherine O’Hara and Eugene Levy. Their participation alone should you clue in on what kind of film this is: a delightful exercise in improvisational comedy. The jokes roll in fast and the spoofs are spot-on (Parker Posey gets a special mention for playing the faux-calm handler with rage issues bubbling up to a tee). And thanks to the mockumentary format, they’re supported by an abundance of visual gags. 

The cherry on top of this fun sundae is the adorable dogs who amusingly participate in human shenanigans. If you're ever looking for a watch that is equal parts comedic and cute, then this underrated comedy gem of a film could be it.

Genre: Comedy, Drama

Actor: Andrew Johnston, Andrew Wheeler, Bob Balaban, Camille Sullivan, Carmen Aguirre, Carrie Aizley, Catherine O'Hara, Christopher Guest, Colin Cunningham, Corrine Koslo, Deborah Theaker, Doane Gregory, Don Lake, Don S. Davis, Ed Begley Jr., Eugene Levy, Fred Willard, Fulvio Cecere, Hiro Kanagawa, Jane Lynch, Jay Brazeau, Jennifer Coolidge, Jim Piddock, John Michael Higgins, Larry Miller, Lewis Arquette, Linda Kash, Lynda Boyd, Malcolm Stewart, Merrilyn Gann, Michael Hitchcock, Michael McKean, Parker Posey, Patrick Cranshaw, Rachael Harris, Scott Williamson, Stephen E. Miller, Steven M. Porter, Teryl Rothery, Tony Alcantar, Will Sasso

Director: Christopher Guest

Rating: PG-13

, 1993

Based on the true story of Daniel “Rudy” Rettinger, this biographical movie follows young Rudy as he pursues his childhood dream of playing football for Notre Dame, despite significant obstacles and copious discouragement from those around him. The movie works not by hitching the action to any major sequences of ball play, but rather to the most remarkable feature of the story: the sheer determination of the title protagonist. The film’s success also largely comes down to a fantastically consistent and earnest performance by Sean Astin, who outshines a very talented supporting cast to the legendary, crowd-stirring end.

Genre: Crime, Drama, History, Romance, Thriller

Actor: Amy Pietz, Charles S. Dutton, Chelcie Ross, Christopher Erwin, Christopher Reed, David Anspaugh, Deborah Wittenberg, Forest Whitaker, Gerry Becker, Greta Lind, Jason Miller, Jim Broadbent, John Beasley, Jon Favreau, Kevin Duda, Lauren Katz, Lili Taylor, Luke Massery, Mary Ann Thebus, Miranda Richardson, Mitch Rouse, Ned Beatty, Ralph Brown, Robert J. Steinmiller Jr., Robert Prosky, Ron Dean, Scott Benjaminson, Sean Astin, Stephen Rea, Vince Vaughn

Director: David Anspaugh, Neil Jordan

Rating: PG

As southern movies go, Fried Green Tomatoes is inoffensively sweet and realistic—it’s not afraid to touch on the genuine issues that plagued America in the 1930s while also cushioning some blows, as feel-good movies are wont to do. But the film seems less interested in presenting a clear picture of the past than it is in telling a specific tale: that of outsiders forming bonds and making it together in an unforgiving society. 

The main narrator is Ninny, an 83-year-old woman seemingly forgotten by everyone except Evelyn, an unhappy housewife who is “too young to be old and too old to be young.” Ninny recalls the stories of Sipsey and Big George, Black laborers who dared to succeed in their deeply racist community; of Smokey, the town outcast, who still helped people even if he was denied it himself; of Ruth, the domestic abuse victim; and of Idgie, the tomboy who spat on the face of all decorum. Then, of course, there’s the unspoken relationship between Ruth and Idgie, which hint at something quite radical for its time. 

These are all the people conventionally denied happy endings, and in period films, you’d expect to be abandoned in tragedy. But here they sing; they win and lose in equal measure, and even though it might seem like light and familiar fare to some, it still goes down heartily and unforgettably—funnily enough, like a plate of fried green tomatoes.

Genre: Comedy, Drama

Actor: Afton Smith, Bob Hannah, Carol Mitchell-Leon, Chris O'Donnell, Chris O'Donnell, Cicely Tyson, Constance Shulman, Danny Nelson, David Dwyer, Evan Lockwood, Fannie Flagg, Gailard Sartain, Gary Basaraba, Grace Zabriskie, Grayson Fricke, Haynes Brooke, Jessica Tandy, Jo Harvey Allen, Kathy Bates, Kathy Larson, LaTanya Richardson Jackson, Lois Smith, Macon McCalman, Mary Stuart Masterson, Mary-Louise Parker, Nancy Moore Atchison, Nick Searcy, Raynor Scheine, Reid Binion, Richard Riehle, Stan Shaw, Suzi Bass, Ted Manson, Tim Scott, Timothy Scott, Tom Even, Wallace Merck

Director: Jon Avnet

Rating: PG-13

Though it paints in overly broad strokes and takes a while to get going, this tale of broken people finding each other eventually reaches an irresistibly feel-good conclusion. Like many good sports movies, Seabiscuit isn't really dependent on the final outcome of a matchup between underdog and high-profile contender. What becomes important, then, is the perseverance of a handful of individuals in doing something just to prove they can beat the odds. And while there aren't actually as many racing sequences in Seabiscuit as you might be led to believe, they're well worth the wait—punctuating the drama with sharp editing and beautiful, period-specific production design.

Genre: Drama, Family, History

Actor: Annie Corley, Cameron Bowen, Camillia Sanes, Carl M. Craig, Chris Cooper, Dan Daily, Danny Strong, David Doty, David McCullough, Dyllan Christopher, Ed Lauter, Eddie Jones, Elizabeth Banks, Gary L. Stevens, Gary McGurk, Gary Ross, Gary Stevens, Gianni Russo, Hans Howes, James Keane, Jeff Bridges, John Walcutt, Ken Magee, Kevin Mangold, Kingston DuCoeur, Mariah Bess, Matt Miller, Michael Angarano, Michael B. Silver, Michael Ensign, Michael O'Neill, Michelle Arthur, Noah Luke, Pat Skipper, Paul Vincent O'Connor, Peter Jason, Richard Reeves, Robin Bissell, Royce D. Applegate, Sam Bottoms, Shay Duffin, Tobey Maguire, Valerie Mahaffey, William H. Macy

Director: Gary Ross

Rating: PG-13

Set during the swingin' seventies, two small town Connecticut families are the subject of this visually stunning and somewhat disturbing drama. With an all-star cast that includes Sigourney Weaver as Janey Carver, an unsatisfied housewife and mother of two and Elijah Wood as her eldest son, there's plenty of star power and drama. In addition, director Ang Lee brings his signature sense of trial and unease while unleashing a quirky and pointed 70's aesthetic.

Genre: Drama

Actor: Adam Hann-Byrd, Allison Janney, Barbara Garrick, Bettina Skye, Byron Jennings, Christina Ricci, Christine Farrell, Colette Kilroy, Colleen Camp, Courtney Peldon, Daniel McDonald, David Krumholtz, Dennis Gagomiros, Donna Mitchell, Elijah Wood, Glenn Fitzgerald, Henry Czerny, Ivan Kronenfeld, Jamey Sheridan, Jessica Stone, Joan Allen, Joe O'Connor, John Benjamin Hickey, Jonathan Freeman, Kate Burton, Katie Holmes, Kevin Kline, Larry Pine, Maia Danziger, Marcell Rosenblatt, Michael Cumpsty, Miles Marek, Nancy Opel, Robert Westenberg, Sarah Thompson, Scott Wentworth, Sigourney Weaver, Tobey Maguire, William Cain

Director: Ang Lee

Rating: R

A true story based film about three girls whose lives become a tragedy shaped by the Rabbit-proof fence, which runs along Australia splitting it to two parts. These girls, daughters of an aboriginal mother and a white father who worked on building the fence and then moved on, get taken from their mother to a so-called re-education camp. This is the story of their escape to find the fence and then their mother, a journey of 1500 miles that they can only do on foot. Tragic, yes, but this is an honest film that sends clear messages without any excessive emotional dwelling.

Genre: Action, Adventure, Drama, History

Actor: Andrew S. Gilbert, Anthony Hayes, Carmel Johnson, Celine O'Leary, David Gulpilil, David Ngoombujarra, Deborah Mailman, Don Barker, Edwina Bishop, Everlyn Sampi, Garry McDonald, Heath Bergersen, Jason Clarke, Ken Radley, Kenneth Branagh, Kenneth Radley, Kizzy Flanagan, Laura Monaghan, Lorna Lesley, Myarn Lawford, Natasha Wanganeen, Ningali Lawford, Richard Carter, Roy Billing, Tianna Sansbury, Trevor Jamieson

Director: Phillip Noyce

Rating: PG