This ranking is based on an algorithm that combines various factors, including the votes of our users and search trends on the internet.

List of Tobey Maguire Movies: Ranked Best To Worst

1. Fear and Loathing in Las Vegas (1998)
18
6
Fear and Loathing in Las Vegas
R
18
6

The dark comedy follows the journey of journalist Raoul Duke and his attorney Dr. Gonzo who drive a red convertible to Las Vegas to cover a motorcycle race. They are, however, carrying a suitcase full of drugs that they consume at an increasing rate. What follows is a psychedelic adventure in search of the American Dream. 

Role:
Hitchhiker
Directed By:
2. Pleasantville (1998)
12
4
Pleasantville
PG-13
12
4

David, who enjoys 1950s TV shows, and Jennifer, who is his opposite in many ways, receive a magical remote control which mysteriously transports them to ‘Pleasantville,’ a simple place from 1950s black-n-white sitcom, with simple-minded people and perfect things. The twin siblings from the real world help add some wonderful colors to the drab lives of the ‘Pleasantville’ people. 

Role:
David
Directed By:
Gary Ross
4. Spider-Man (2002)
38
13
Spider-Man
PG-13
38
13

Brilliant but socially awkward high school student Peter Parker gets bitten by a radioactive spider on a field trip and gains spider-like abilities and super strength. Following a family tragedy, he learns to use his superpowers only for good, as he faces an evil millionaire to save his aunt May and his crush Mary Jane Watson.

Role:
Spider-Man / Peter Parker
Directed By:
Awards:
MTV Movie & TV Award for Best Kiss
5. Spider-Man 2 (2004)
32
11
Spider-Man 2
PG-13
32
11

Despite desperate attempts to balance his life as crime-fighting neighborhood hero Spider-Man, Peter Parker's grades are falling, he loses his jobs regularly, and his love interest is engaged to someone else. Dejected, he gives up his alter ego, but eccentric scientist Dr. Otto Octavius, now tentacled villain Doctor Octopus, holds him responsible for a botched nuclear experiment.

Role:
Spider-Man / Peter Parker
Directed By:
6. The Cider House Rules (1999)
11
4
The Cider House Rules
PG-13
11
4

Orphan Homer Wells is lovingly brought up in a Maine orphanage by Dr. Wilbur Larch, who performs secret abortions for people in need. As Homer grows up skillful in obstetrical duties he leaves the orphanage because he doesn’t agree with Larch on abortion, but quickly starts questioning his choices after he starts working at an apple orchard.  

Role:
Homer Wells
Directed By:
Lasse Hallström
8. Seabiscuit (2003)
10
4
Seabiscuit
PG-13
10
4

Depression era’s true story about thoroughbred Seabiscuit who, though relatively undersized and with slight limp, became one of the most successful racehorses. Car-dealer Charles Howard bought the disgraced horse on suggestion of down-&-out trainer Tom Smith, who selected Red Pollard as his jockey. Forming a close bond with them, Seabiscuit achieved victories that boosted spirits of his team as well as the nation. 

Directed By:
Gary Ross
9. This Boy's Life (1993)
9
3
This Boy's Life
R
9
3

This Boy’s Life is an American coming-of-age drama film, which takes us  to the 1950s. It tells the story of a rebellious teenager Toby and his abusive stepfather Dwight. Dwight believes that the best way to discipline his troubled stepson is violence. However, as his abuse intensifies, Toby plans an escape. 

Starring:
Directed By:
Michael Caton-Jones
11. The Great Gatsby (2013)
26
10
The Great Gatsby
PG-13
26
10

Based on a popular 1925 novel of the same name by F Scott Fitzgerald, this Oscar winning romantic drama revolves around Nick Carraway, a writer and wall-street trader, who is drawn into his millionaire neighbor Jay Gatsby’s past and lifestyle. 

Starring:
Leonardo DiCaprio, Joel Edgerton, Isla Fisher, Amitabh Bachchan, Jason Clarke, Carey Mulligan, Elizabeth Debicki
Directed By:
Baz Luhrmann
12. Wonder Boys (2000)
9
4
Wonder Boys
R
9
4

Professor Grady Tripp teaches creative writing but is unable to overcome his writer’s block and complete his novel. Besides that, his platter is full with – his third wife leaves him, his literary agent arrives to push him to complete his manuscript, his married girlfriend becomes pregnant with their child, his troubled student has problems with life. Can the weekend accommodate any more complications?

Role:
James Leer
Starring:
Robert Downey Jr., Michael Douglas, Frances McDormand, Katie Holmes
Directed By:
Curtis Hanson
13. Brothers (2009)
11
5
Brothers
R
11
5

Captain Sam Cahill’s helicopter is shot down while he is on duty in Afghanistan. His brother Tommy takes over the responsibilities of his brother’s family comprising his wife and two daughters. When Sam returns from captivity, he is emotionally scarred and finds it difficult to accept the changes that have taken place in his absence.

Role:
Capt. Sam Cahill
Starring:
Jake Gyllenhaal, Sam Shepard, Natalie Portman, Mare Winningham, Bailee Madison, Carey Mulligan
Directed By:
Jim Sheridan
14. Pawn Sacrifice (2014)
8
4
Pawn Sacrifice
PG-13
8
4

The biographical film about American Grandmaster Bobby Fischer focuses mainly on his challenge against Soviet chess champion Boris Spassky during the Cold War, and the 1972 World Chess Championship match between the two. To accomplish his dream of being the youngest world champion, Fischer has to fight his own escalating paranoia as well as deal with the pressures from the two superpowers. 

Role:
Bobby Fischer
Starring:
Liev Schreiber, Michael Stuhlbarg, Peter Sarsgaard, Edward Zinoviev
Directed By:
Edward Zwick
15. Labor Day (2013)
8
4
Labor Day
PG-13
8
4

A depressed single mother and her son offer a ride to a wounded and fearsome man. However, they eventually come to know that he is an escaped convict, and think of ways to escape from him. 

Role:
Adult Henry
Starring:
Kate Winslet, Josh Brolin, Gattlin Griffith, Tom Lipinski
Directed By:
Jason Reitman
16. Empire Records (1995)
8
4
Empire Records
PG-13
8
4

Employees working at a small record shop, help their manager collect money in order to buy the enterprise. However, now they must again unite to fight off a corporate giant. 

Starring:
Renee Zellweger, Liv Tyler, Renée Zellweger, Johnny Whitworth, Debi Mazar, Robin Tunney
Directed By:
Allan Moyle
17. Ride with the Devil (1999)
7
3
Ride with the Devil
R
7
3

Based on a novel named ‘Woe to Live On’, this Western war drama film takes us to the time of the American Civil War. It revolves around a group of men, who join the First Missouri Irregulars, a guerrilla unit loyal to the Confederacy.

Role:
Jake Roedel
Starring:
Jonathan Brandis, Jonathan Rhys Meyers, Simon Baker, Mark Ruffalo, Jim Caviezel, Skeet Ulrich, Jeremy W. Auman
Directed By:
18. Spider-Man 3 (2007)
24
14
Spider-Man 3
PG-13
24
14

Just as Peter Parker seems to have achieved a balance between school, love life, and his vigilante alter-ego, a new threat arises when his suit turns black, enhancing his powers and amplifying the dark side of his character. He also has to tackle his old-friend-turned-sworn-enemy Harry Osborn and bring to justice uncle Ben's real killer, the Sandman.

Role:
Spider-Man / Peter Parker
Starring:
Bryce Dallas Howard, Topher Grace, Joe Manganiello, James Cromwell, Bruce Campbell, Cliff Robertson, Willem Dafoe
Directed By:
19. The Details (2011)
5
3
The Details
R
5
3

The Details is a black comedy drama film which tells the story of Jeff, a simple family man living in a suburban neighborhood, who is attempting to grow the perfect lawn. All he is trying to do is get rid of his pest problem, but it leads to a wild chain of domestic problems leading to infidelity and murder.

Role:
Jeff Lang
Starring:
Kerry Washington, Laura Linney, Ray Liotta, Elizabeth Banks, Gary Schwartz, José Gandara
Directed By:
Jacob Estes
20. The Good German (2006)
6
4
The Good German
R
6
4

The Good German is a mystery thriller film which tells the story of a journalist who is in Berlin shortly after the Second World War to cover the Potsdam Conference. He soon gets involved in a murder investigation which involves his former lover and driver.

Role:
Tully
Starring:
Cate Blanchett, George Clooney, Beau Bridges, Tony Curran
Directed By:
21. S.F.W. (1994)
5
3
S.F.W.
R
5
3
Starring:
Reese Witherspoon, Jake Busey, Pamela Gidley, Stephen Dorff
Directed By:
Jefery Levy
22. Don's Plum (2001)
4
3
Don's Plum
4
3
Role:
Ian
Starring:
Jeremy Sisto, Leonardo DiCaprio, Scott Bloom, Kevin Connolly, Jenny Lewis
Directed By:
R.D. Robb
23. Joyride (1997)
3
3
Joyride
R
3
3
Role:
J.T.
Starring:
Adam West, Benicio Del Toro, Amy Hathaway, Wilson Cruz, Christina Zilber
Directed By:
Quinton Peeples
24. Rodney Dangerfield: Opening Night at Rodney's Place (1989)
7
3
Rodney Dangerfield: Opening Night at Rodney's Place
TV-MA
7
3
Starring:
Rodney Dangerfield, Tim Allen, Richard Epcar, Bernadette Birkett
Directed By:
Gregory Sills
25. A Child's Cry for Help (1994)
5
3
A Child's Cry for Help
5
3
Starring:
Pam Dawber, Daniel Benzali, Lisa Jakub, Daniel Hugh Kelly
Directed By:
Sandor Stern
26. Duke of Groove (1996)
5
3
Duke of Groove
5
3
Starring:
Udo Kier, Uma Thurman, Kiefer Sutherland, Elliott Gould
Directed By:
Griffin Dunne
27. Tales from the Whoop: Hot Rod Brown Class Clown (1990)
4
3
Tales from the Whoop: Hot Rod Brown Class Clown
4
3
Role:
Hot Rod Brown
Starring:
Whoopi Goldberg, Gloria Gifford, Laura Jacoby, Daniel Collins
Directed By:
Rocco Urbisci
28. Spoils of War (1994)
4
3
Spoils of War
4
3
Role:
Martin
Starring:
Rhea Perlman, Kate Nelligan, John Heard, Andrea Roth
Directed By:
David Greene
29. Healer (1994)
3
3
Healer
PG
3
3
Starring:
David McCallum, Turhan Bey, Lee Patterson, DeLane Matthews
Directed By:
John G. Thomas
30. Revenge of the Red Baron (1994)
2
3
Revenge of the Red Baron
PG-13
2
3
Role:
Jimmy Spencer
Starring:
Mickey Rooney, Laraine Newman, Cliff De Young, John C. McDonnell
Directed By:
Robert Gordon

TV Shows

Eerie, Indiana
13
3
Eerie, Indiana
TV-Y7
13
3
Starring:
Ray Walston, Claude Akins, Denise Richards, Tony Jay, Mary-Margaret Humes, Justin Shenkarow, Omri Katz
Directed By:
Tim Hunter, Bryan Spicer, Bob Balaban, Ken Kwapis, Joe Dante
Bob Dylan: Things Have Changed (2000)
8
2
Bob Dylan: Things Have Changed
8
2
Role:
Himself
Starring:
Katie Holmes, Robert Downey Jr., Michael Douglas, Bob Dylan
Directed By:
Curtis Hanson
Great Scott!
7
3
Great Scott!
7
3
Role:
Scott Melrod
Starring:
Jack Black, Marley Shelton, Sarah Koskoff, Kevin Connolly
Directed By:
Brad Silberling
Tracey Takes On...
7
3
Tracey Takes On...
7
3
Starring:
Gary Oldman, John Stamos, Jennifer Jason Leigh, Giovanni Ribisi, Billy Connolly, Alanna Ubach, Jon Favreau
Directed By:
Thomas Schlamme, Don Scardino, Michael McKean, Michael Lange, Simon Curtis
Roseanne
31
13
Roseanne
TV-PG
31
13
Starring:
Sara Gilbert, Johnny Galecki, Ed Asner, Christina Pickles, Tony Curtis, Bob Odenkirk, Shelley Winters
Directed By:
The Spoils of Babylon
8
4
The Spoils of Babylon
TV-14
8
4
Role:
Devon Morehouse
Starring:
David Spade, Will Ferrell, Kristen Wiig, Michael Sheen, Timothy Francis Robbins, Molly Shannon, Jessica Alba
Directed By:
Matt Piedmont
Seduced by Madness: The Diane Borchardt Story
6
3
Seduced by Madness: The Diane Borchardt Story
R
6
3
Role:
Chuck Borchardt
Starring:
Eric Dane, Ann-Margret, Amy Smart, Alanna Ubach, Hedy Burress, Leslie Hope
Directed By:
John Patterson
1st & Ten
6
3
1st & Ten
6
3
Starring:
Yolanda Foster, Lawrence Taylor, Chazz Palminteri, O. J. Simpson, Christopher Meloni, O.J. Simpson, Yolanda Hadid
Directed By:
Peter Bonerz, Bruce Seth Green, Stan Lathan, Burt Brinckerhoff, Jonathan Debin
Jake and the Fatman
7
4
Jake and the Fatman
7
4
Starring:
Dick Van Dyke, Bruce Greenwood, Marcia Cross, Danny Trejo, Robert Reed, Ernest Borgnine, Cary-Hiroyuki Tagawa
Directed By:
Blossom
9
6
Blossom
TV-PG
9
6
Starring:
Joely Fisher, A. J. Langer, David Arquette, Jane Leeves, Estelle Getty, Phyllis Diller, Christine Taylor
Directed By:
Zane Buzby, Bill Bixby, Ted Wass, Gil Junger, Peter Baldwin
Walker, Texas Ranger
11
9
Walker, Texas Ranger
11
9
Starring:
Robert Englund, Danica McKellar, Adam Beach, Rod Taylor, Sammo Hung, RuPaul, David Keith
Directed By:
Michael Preece, Tony Mordente, Jerry Jameson, Eric Norris, Christian I. Nyby II

Narrator/Dubbing

Beyond All Boundaries (2009)
8
2
Beyond All Boundaries
8
2
Role:
Pvt. George Strang (voice)
Starring:
Kevin Bacon, Corbin Bleu, Justin Long, Blythe Danner, Neil Patrick Harris, John Goodman, Viola Davis
Directed By:
David Briggs
Cats & Dogs (2001)
16
16
Cats & Dogs
PG
16
16

Cats & Dogs is a spy action-comedy film which revolves around an espionage war going on between dogs and cats, about which their human owners are totally unaware of. 

Role:
Lou (voice)
Starring:
Jeff Goldblum, Billy West, Susan Sarandon, Joe Pantoliano, Miriam Margolyes, Michael Clarke Duncan, Charlton Heston
Directed By:
Lawrence Guterman

Animation Movies

The Boss Baby (2017)
9
6
The Boss Baby
PG
9
6

An infant wearing a suit, and carrying a briefcase, pairs up with his 7 year old-brother, to stop the dastardly plot of the CEO of Puppy Co. 

Role:
Adult Tim / Narrator (voice)
Starring:
Lisa Kudrow, Jimmy Kimmel, Steve Buscemi, Alec Baldwin, Lisa Kudrow
Directed By:
Tom McGrath

Special Appearance/Cameo

The Wizard (1989)
9
6
The Wizard
PG
9
6

After his little brother Jimmy is put in a mental institution, Corey manages to break him out, and the two run off together to California. He soon discovers that Jimmy is a master when it comes to video games, and they decide to travel to take part in a video game competition. Meanwhile, however, their parents have hired someone to track down the children.

Role:
Lucas' Goon at Video Armageddon (uncredited)
Starring:
Fred Savage, Christian Slater, Wendy Phillips, Sam McMurray
Directed By:
Todd Holland

Tobey Maguire Awards

MTV Movie & TV Awards
Spider-Man Best Kiss 2003