3 Movies Like Mystery Men (1999)

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, Harry Singleton, 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

It’s very interesting, if not startling, to see an earnest movie made about the white upper class these days. Metropolitan is one such film, and even though it was released in the ’90s, it still stands the test of time precisely because it neither judges nor defends the group of WASPs it follows. It simply shows them in all their elegance and sophistication, as well as their insulation and irony.

Metropolitan takes place in the upper crust of New York debutante society, during Christmas vacation, where soirees are rampant and afterparties even more so. The young-adult leads who navigate the scene in their expensive clothes and self-important aura recall a Scott Fitzgerald novel, or if you like, Gossip Girl episode. But instead of falling into tragedies, these characters just end up in silly but relatable mishaps and misunderstandings: they’re just kids after all. And as high and mighty as they may seem, whiling away in tall Park Avenue apartments, they’re still prone to the universal pains that haunt and shape teenagers. Expect to see heartbreak, jealousy, and longing even among the brightest and wealthiest of New York.

Genre: Comedy, Drama, Romance

Actor: Alice Connorton, Bryan Leder, Carolyn Farina, Chris Eigeman, Donal Lardner Ward, Edward Clements, Francis Creighton, Isabel Gillies, Taylor Nichols, Thomas R. Voth, Will Kempe

Director: Whit Stillman

Rating: PG-13

3 Movies Like Mystery Men (1999)

1. Pleasantville, 1998

2. Metropolitan, 1990

3. Galaxy Quest, 1999