13. THE GOOD GERMAN (2006)

Director: Steven Soderbergh.  Writer: Paul Attanasio.  Starring George Clooney, Cate Blanchett, Tobey Maguire, Beau Bridges.  

Steven Soderbergh’s period thriller is less about plot and more…much more…about style.  Shot in black-and-white in an unusual 1.66:1 picture ratio, “The Good German” is trying its best to be a modern update of “Casablanca,” an impossible task to which “The Good German” gives its all.  Maguire plays Tully, an American soldier assigned to be the driver of magazine correspondent Jake Geismer (George Clooney).  Tully, who has a side business as a black marketeer, is found murdered early in the film, and much of Jake’s preoccupation is to solve his driver’s murder.  Maguire remains a presence throughout the entire film, and even though the film was a critical and commercial flop, the quality of the acting of his co-stars really ups Maguire’s game.

12. THE GREAT GATSBY (2013)

Director: Baz Luhrmann.  Writers: Baz Luhrmann, Craig Pearce, based on the novel by F. Scott Fitzgerald.  Starring Leonardo DiCaprio, Tobey Maguire, Carey Mulligan, Joel Edgerton.  

Baz Luhrmann’s take on the classic F. Scott Fitzgerald novel is as big and flashy and gaudy as you might expect from the Aussie filmmaker, and like many Luhrmann films, the critical reaction to the film was all over the place.  Maguire, however, received generally good reviews as Nick Carroway, an aspiring writer and friend of Jay Gatsby (Leonardo DiCaprio) who is a calm observer to Gatsby’s fall and serves as the audience’s eyes and ears to the events precipitating it.  Nick is the detached center of the action, and Maguire follows that path expertly.

11. RIDE WITH THE DEVIL (1999)

Director: Ang Lee.  Writer: James Schamus.  Starring Tobey Maguire, Skeet Ulrich, Jewel, Jeffrey Wright.  

Maguire’s second collaboration with director Ang Lee is set during the Civil War with Maguire playing Missourian Jake Roedel whose best friend Jack Bull Chiles (Skeet Ulrich) has just lost his father, who was murdered by pro-Union splinter group, The Jayhawkers.  The pair swear vengeance against The Jayhawkers and join a pro-Confederacy group, The Bushwackers, to obtain justice.  Maguire had to undergo a strenuous three-week boot camp that often necessitated 16-hour workdays in order to learn how to learn such necessities as how to load and fire period weaponry.  The result is Maguire turning in one of his toughest film performances.

10. BROTHERS (2009)

Director: Jim Sheridan.  Writer: David Benioff.  Starring Tobey Maguire, Jake Gyllenhaal, Natalie Portman, Sam Shepard, Mare Winningham.  

Based on Susanne Bier’s Danish film “Brødre,” Jim Sheridan’s remake is set in Afghanistan and Denmark, as Capt. Sam Cahill (Maguire), about to return for his fourth tour of duty in Afghanistan, learns that his brother Tommy (Jake Gyllenhaal) is about to be released from prison.  Sam nonetheless goes through with his deployment and is soon reported as being killed in action.  In actuality, he is being held as a POW by the Taliban.  Thinking that Sam is dead, Tommy begins a romantic relationship with Sam’s grieving wife Grace (Natalie Portman) an affair that is jeopardized when Sam is finally rescued and returns home.  For his performance as Sam, Maguire earned his first Golden Globe nomination as Best Actor.

9. PAWN SACRIFICE (2015)

Director: Edward Zwick.  Writer: Steven Knight.  Starring Tobey Maguire, Peter Sarsgaard, Liev Schreiber, Michael Stuhlbarg.  

In this biopic set in the world of competitive chess, Maguire portrays legendary chess master Bobby Fischer on the eve of his 1972 World Championship chess match with Soviet Boris Spassky (Liev Schreiber).  Much of the film is told in flashback as we are shown the roots of Fischer’s severe mental challenges that result in explosive emotional explosions on the eve of the match which merely feed his lifelong paranoia and delusional psychosis.  Steven Knight’s script would give any actor a lot to chew on, and under Edward Zwick’s direction, Maguire dives right in, creating a fascinating figure of an enormously talented individual who can’t get out of his own way.

8. DECONSTRUCTING HARRY (1997)

Writer/Director: Woody Allen.  Starring Woody Allen, Richard Benjamin, Kirstie Alley, Judy Davis, Billy Crystal, Tobey Maguire. Elisabeth Shue, Robin Williams.  

Being asked to appear in a Woody Allen comedy was, at one time, an indication that you have really made it in Hollywood.  Maguire’s contribution is not enormous in length, but he makes his limited time onscreen count as Harvey, a fictional creation in the mind of novelist Harry Block (Allen).  Harvey is a young man obsessed by sex (projection, much?) who is mistakenly whisked away by Death.  Maguire, who is rarely cast in a comedic role, looks like he’s having a blast, and he fits very neatly into this A-list ensemble.

7. THE CIDER HOUSE RULES (1999)

Director: Lasse Hallström.  Writer: John Irving, based on his novel.  Starring Tobey Maguire, Charlize Theron, Michael Caine, Paul Rudd, Erykah Badu.  

Maguire received his first cast ensemble nomination from the Screen Actors Guild for his performance as Homer Wells, a young orphan who has been returned twice by foster parents to his Maine orphanage.  He is taken under the wing of the orphanage’s doctor, Wilbur Larch (Michael Caine in an Oscar-winning performance), who also performs back-alley abortions.  Dr. Larch’s aim is to groom Homer to succeed him in the abortion business, but Homer, who has moral qualms about abortions, declines, hoping to leave the orphanage to see the world.  Maguire plays Homer as an innocent, so that when the realities of life hit him, it hits him especially hard.

6. BABYLON (2022)

Tobey Maguire made his career playing nice guys and a friendly neighborhood Spider-man. So his brief appearance late in “Babylon” is as shocking as his surprise appearance in 2021’s “Spider-Man: No Way Home.” Maguire plays a seedy and extremely wealthy ne’er-do-well in Damian Chazelle’s sprawling film, the type of decayed Hollywood high roller who is as comfortable pitching outlandish movie ideas as he is walking through a grotesque sex dungeon. Maguire seemingly relishes the chance to break bad, and his unnerving performance is a standout in the film, even if it’s but a small part of the lengthy “Babylon” running time.

5. PLEASANTVILLE (1998)

Writer/Director: Gary Ross.  Starring Tobey Maguire, Jeff Daniels, Joan Allen, William H. Macy, J.T. Walsh, Reese Witherspoon.  

In Gary Ross’ satire of small-town suburban life, Maguire teams up with Reese Witherspoon as fraternal twins who are couldn’t be more opposite — Jennifer is shallow but popular and David is an introvert who spends his time watching TV marathons of his favorite show, the 1950s black-and-white sitcom “Pleasantville.”  One day, as they fight over the remote control, David and Jennifer find themselves transported back in time as the siblings in the old sitcom.  As polar opposites, Maguire and Witherspoon make a great team together, and Maguire as David has one of the best character arcs he’s had in his career.

4. SEABISCUIT (2003)

Writer/Director: Gary Ross.  Starring Tobey Maguire, Jeff Bridges, Chris Cooper, Elizabeth Banks, Gary Stevens, William H. Macy.  

In his second collaboration with writer/director Gary Ross, Maguire utilized his slight build to become an absolutely believable real-life jockey named Red Pollard, who was one of the guiding forces behind Seabiscuit’s legendary racing career.  Finding a suitable jockey to ride the feisty horse was not an easy task, but once trainer Tom Smith (Chris Cooper) sees the temperamental jockey in action, he knows that he has found just the right rider for Seabiscuit.  As part of the ensemble cast of “Seabiscuit,” Maguire earned his second nomination from the Screen Actors Guild.

3. THE ICE STORM (1997)

Director: Ang Lee.  Writer: James Schamus.  Starring Joan Allen, Kevin Kline, Sigourney Weaver, Tobey Maguire, Christina Ricci, Elijah Wood, Katie Holmes, David Krumholtz.  

In Maguire’s first major artistic success (and his first collaboration with director Ang Lee), he plays Paul Hood, a boarding school student who lives in an upper-class Connecticut suburb in 1973.  While his father Ben (Kevin Kline) is sleeping around behind his wife’s (Joan Allen) back, Paul has fallen for a classmate Libbets (Katie Holmes), even though his roommate Francis (David Krumholtz) has the same inclination and appears to have made further progress. It was a powerful introduction to movie audiences that Maguire has been able to parlay into a 25-year film career.

2. WONDER BOYS (2000)

Director: Curtis Hanson.  Writer: Steve Kloves.  Starring Michael Douglas, Tobey Maguire, Frances McDormand, Katie Holmes, Robert Downey Jr.  

Although Michael Douglas’ college professor Grady Tripp is the focus of Curtis Hanson’s film, the key supporting role in the film is Maguire’s part as James Leer, a student of Grady’s who has demonstrated tendencies that may be interpreted as being at least depression or possibly suicidal tendencies.  Nonetheless, James has sex with Grady’s book editor Terry Crabtree (Robert Downey Jr.) and soon begins writing a novel of his own.  Maguire has been a part of several film ensembles in his career. but “Wonder Boys” marks one of his best, placing his very complex James amid other screwed-up characters and fitting right in.

1. THE SPIDER-MAN Series (2002, 2004, 2007)

Director: Sam Raimi.  Writers: Various.  Starring Tobey Maguire, Kirsten Dunst, James Franco, Rosemary Harris, J.K. Simmons.  

It’s rare in these photo galleries that performances in comic-book tentpole movies rise to the top of an actor’s filmography, but Maguire’s work as Peter Parker and Spider-Man really is something special.  Even though he was 27 years-old at the time of the release of the first “Spider-Man” film, Maguire’s youthful looks make him thoroughly believable as high-school student Peter Parker, and his chemistry with Kirsten Dunst really makes you believe that Peter and Dunst’s Mary Jane Watson have a crush on one another that could lead to something more.  Yes, after three Spider-Man films, Maguire was replaced by two other actors, but even as the latest Spider-Man film nears release, I can’t help thinking back to the actor who started it all.