Tobey Maguire Career

Fear And Loathing In Las Vegas (7.6)

In this widely outrageous comedy, Fear and Loathing in Las Vegas (1998) follows Johnny Depp and Benicio Del Toro throughout their insane, drug-induced adventures. However, while the film mostly follows these two characters, Maguire still stands out in the role of Hitchhiker.

With a lot of great humor and a very unique way to tell a story, Fear and Loathing in Las Vegas definitely stands out from other films in the genre. Though Maguire isn’t most known for his role in this film, it is definitely a more unique performance for the actor.

25th Hour (7.6)

Directed by Spike Lee, 25th Hour is centered on a drug dealer trying to reevaluate his life within a single day. Surprisingly, for one of Maguire’s highest-rated movies, the actor doesn’t actually play a role within the film.

Instead, Maguire produced the film along with Spike Lee, making this a bit more of an unconventional project for him. Fortunately, the film still holds strong and includes great performances from Edward Norton and the late Phillip Seymore Hoffman, making it easy to see why it falls as one of Maguire’s top films overall.

Pleasantville (7.5)

Pleasantville (1998) stars Maguire as David alongside Reese Witherspoon as his sister, Jennifer. While the duo are completely different personalities, the two must learn to live with one another after suddenly being transported into the world of Pleasantville, a 1950’s sitcom series.

Not only is the film absolutely hilarious, but it is very charming in a way that isn’t seen terribly often anymore. With great themes and interactions between the other cast members, Pleasantville is easily one of Maguire’s best movies.

The Cider House Rules (7.4)

With Maguire in the lead role of Homer Wells, The Cider House Rules (1999) is a great, underrated romantic drama with strong performances all around. Featuring other actors like Charlize Theron and Michael Cain, there was a lot to appreciate about this film overall.

Centered on a young doctor who leaves the orphanage where he was raised to go out and see the world, The Cider House Rules is a truly heartwarming tale, however heartbreaking it may be at times. Based on the novel of the same name by John Irving, it is easy to see why the film ranks a bit higher than others to feature the actor.

The Ice Storm (7.4)

Shortly before the release of Deconstructing Harry, Maguire found himself in the much bigger role of Paul Hood in 1997’s The Ice Storm. From director Ang Lee, The Ice Storm is centered around a suburban family with sex and drugs being a common focus throughout the film.

While it may seem very weird at times, the film actually maintains a believable narrative, however crazy some aspects may be. Likewise, though Maguire isn’t the central focus of the film, he still pulls off the role of Paul rather well.

Deconstructing Harry (7.4)

Though it is not one of Woody Allen’s more memorable films, Deconstructing Harry (1997), still has its merits. Centered on a writer trying to reignite his motivation, the film mostly follows Woody Allen’s character, Harry Block, as he uses past situations and characters throughout his daily life.

In this film, Maguire plays Harvey Stern, a sex-obsessed man who finds himself wrongfully claimed by Death. Though Maguire’s role in the film isn’t too lengthy, it is still one of the more humorous moments from it. While the film itself may not be for everyone, it is easy to see why it scored a bit higher than others to have featured Maguire.

Spider-Man (7.3)

tobey spiderman Beat the sequel by the number of votes, it is not hard to see how Spider-Man (2002) could be considered marginally better than the sequel. As one of the earlier superhero films, and especially as the first Spider-Man film, this movie set a really high bar for everything the genre could accomplish.

Not only was this film well-received by audiences and comic fans alike, but it would really serve as a staple for the genre going forward. Thanks to Sam Raimi’s strong, guiding hand, Spider-Man is not only one of Maguire’s best films, but one of the best superhero films from this time period as well.

Spider-Man 2 (7.3)

To this day, many Spider-Man fans consider Spider-Man 2 (2004) to be the greatest features for the Web-Head to date. With a strong plot, great performances, and wonderful action sequences, it is easy to see how the film still holds up. Some thinks that in real life tobey maguire spider man

Of course, Maguire reprises his role as Peter Parker, this time facing his own inner struggles on top of the looming threat of Doctor Octopus (Alfred Molina). Furthermore, seeing the way Spider-Man wins in the end is a bit more unconventional, serving as a great reminder as to why everyone loves the hero to begin with. Given all the strengths of this movie alone, it is easy to see why it is considered one of Maguire’s best films.

Tobey Maguire Personal Life & Legacy

Quotes from Tobey Maguire

“There are so many things I want to do. I want to work with great filmmakers, great actors, great scripts. And there’s no reason for me to do anything short of that because I’m 24, I don’t have a family, I don’t need to make tons of money, and I’m not dying to get famous.” – Tobey Maguire

“I just try to try to keep an attitude that I don’t know what I’m doing. Not to the point where I’m beating myself up, but I just go in thinking that I have a lot to learn. And I hope I still have that attitude 30 years from now.” – Tobey Maguire

“If you’re sitting in the audience, you probably can’t see the preparation and work that goes into creating a great scene or a great part, but I can assure you that a good film depends on a lot of different things falling perfectly into place.” – Tobey Maguire

“The most attention I get is in a book store or video shop when I go to the foreign film section. Sometimes that can be fun, but usually, those women want to talk about philosophy or something very dense. It’s not like they’re tearing off my shirt, you know.” – Tobey Maguire

“To me, the whole idea of fame and I think it can be a real test of somebody, of who they are. You know, ’cause some strange things happen. I’ve seen some peculiar things as far as a person just living their life.” – Tobey Maguire