4 Best Movies by Tobey Maguire On Cineplex Canada

1. Wonder Boys, 2000

Michael Douglas plays Grady Tripp, a craggy, lovable English professor struggling to finish the follow-up to a very successful first novel. It has taken him 7 years, and it's an obvious metaphor for his ridiculous life. The character navigates various tragicomic dilemmas with a stellar supporting cast including Frances McDormand, Tobey Maguire, and Katie Holmes. His editor is Robert Downey Jr. and his nemesis is Rip Torn. Bob Dylan wrote the theme song. How do you not love this movie? It's one of those films that feels like a warm, cozy house (despite the fact that it takes place in a Pittsburgh winter), and it's a great blend of humor and drama.

2. Seabiscuit, 2003

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.

3. Pleasantville, 1998

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.

4. The Ice Storm, 1997

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.