5 Best Movies to Watch by Tobey Maguire

Staff & contributors

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.

Genre: Comedy, Drama

Actor: Alan Tudyk, Bingo O'Malley, Charis Michelsen, Elisabeth Granli, Frances McDormand, George Grizzard, James Ellroy, James Kisicki, Jane Adams, John W. Iwanonkiw, Katie Holmes, Kelly Bishop, Michael Cavadias, Michael Douglas, Philip Bosco, Richard Knox, Richard Thomas, Rip Torn, Rob McElhenney, Robert Downey Jr., Sean King, Tobey Maguire, Victor Quinaz, Yusuf Gatewood

Director: Curtis Hanson

Rating: R

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, 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, 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

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, Danny Strong, Dawn Cody, Denise Dowse, Don Knotts, Giuseppe Andrews, J.T. Walsh, Jane Kaczmarek, Jason Behr, Jeff Daniels, Jenny Lewis, Joan Allen, John Ganun, Justin Nimmo, Kai Lennox, Kevin Connors, Lela Ivey, Maggie Lawson, Marc Blucas, Marissa Ribisi, Marley Shelton, McNally Sagal, Natalie Ramsey, Paul Morgan Stetler, Paul Walker, Reese Witherspoon, Tobey Maguire, 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, Nancy Opel, Robert Westenberg, Sarah Thompson, Scott Wentworth, Sigourney Weaver, Tobey Maguire, William Cain

Director: Ang Lee

Rating: R

Pawn Sacrifice is a period drama about famed chess player Bobby Fischer (Tobey Maguire), following Fischer’s rise from his childhood in Brooklyn through to his famed matchup with Soviet Grandmaster Boris Spassky (Liev Schreiber) at the 1972 World Chess Championship. The film captures Fischer’s adolescence as a time of burgeoning mastery of the game, while struggling in a fatherless home and beset by early signs of mental illness. Set during the height of the Cold War, tensions between the United States and Russia play a critical role in the story, as they fuel many of Fischer’s fears and anxieties over perceived Russian spying and surveillance. His paranoia reaches a fever pitch in Reykjavik, Iceland, the site of his famous duel with Spassky for the world championship, leading to a remarkably compelling finale. Writer director Steven Knight and director Edward Zwick have crafted a striking depiction of a real-life genius grappling with fraying sanity, and Maguire is stunningly evocative as the abrasive and acerbic Fischer. For the viewer, no advanced knowledge of chess is necessary to enjoy this vivid depiction of one man’s historical achievement in the face of profound mental disturbance.

Genre: Drama, Thriller

Actor: Aiden Lovekamp, Al Vandecruys, Alain Goulem, Aleksandr Gorchilin, André Sogliuzzo, Andreas Apergis, Arthur Holden, Benoit Priest, Bobo Vian, Brent Skagford, Brett Watson, Carlo Mestroni, Conrad Pla, Dennis Staroselsky, Edward Yankie, Edward Zinoviev, Ellen David, Eric Lee Huffman, Eugene Nomura, Evelyne Brochu, François Ducharme, Glen Bowser, Igor Ovadis, Ilia Volok, Joe Cobden, John Maclaren, Jonathan Dubsky, Katie Bird Nolan, Liev Schreiber, Lily Rabe, Lydia Zadel, Mark Slacke, Matt Keyes, Michael Stuhlbarg, Natalija Ugrina, Nathaly Thibault, Norman Lehnert, Peter Janov, Peter Sarsgaard, Raphael Grosz-Harvey, Richard Jutras, Robin Weigert, Roc LaFortune, Sam Stone, Seamus Davey-Fitzpatrick, Shawn Campbell, Sophie Nélisse, Spiro Malandrakis, Tobey Maguire, Vitali Makarov, Vito DeFilippo, Zach Fraser

Director: Edward Zwick

Rating: PG-13