7 Best Movies to Watch by Tobey Maguire

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, Lenora Nemetz, 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

It’s not easy to watch films about child abuse, so it makes sense that This Boy’s Life wouldn’t be a hit blockbuster, but it’s still surprising how this 90’s film still remains an underrated gem. For starters, big names like Robert De Niro and Leonardo DiCaprio (in his breakthrough role), star as leads, and their performances are top-notch. But what ultimately makes the film a good movie to watch is how surprisingly nuanced it depicts child abuse and neglect. Part of this nuance is due to being based on a true memoir, but director Michael Caton-Jones and writer Robert Getchell capture the insidious way abuse can start and become normalized in a household while still highlighting the ways survivors can escape. It’s not an easy watch, but This Boy’s Life is a moving drama that deserves more time in the sun.

Genre: Drama

Actor: Carla Gugino, Chris Cooper, Eliza Dushku, Ellen Barkin, Frank C. Turner, Gerrit Graham, Jonah Blechman, Kathy Kinney, Leonardo DiCaprio, Morgan Brayton, Robert De Niro, Sean Murray, Tobey Maguire, Tracey Ellis, Travis MacDonald, Zachary Ansley

Director: Michael Caton-Jones

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, 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

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

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 Dubois, Al Vandecruys, Alain Goulem, Aleksandr Gorchilin, Alexandre Gorchkov, André Sogliuzzo, Andreas Apergis, Andrew Peplowski, Arthur Holden, Benoit Priest, Bobby Fischer, Bobo Vian, Brent Skagford, Brett Watson, Carlo Mestroni, Conrad Pla, David Pryde, 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, Maurice Demers, Michael Stuhlbarg, Mohsen El Gharbi, Natalija Ugrina, Nathaly Thibault, Norman Lehnert, Peter Janov, Peter Sarsgaard, Raphael Grosz-Harvey, Richard Jutras, Robin Weigert, Roc LaFortune, Sam Stone, Seamus Davey-Fitzpatrick, Shanmugasunder Chetty, Shawn Campbell, Sophie Nélisse, Spiro Malandrakis, Tobey Maguire, Vitali Makarov, Vito DeFilippo, Zach Fraser

Director: Edward Zwick

Rating: PG-13