The Best Tobey Maguire Movies, Ranked
Tobey Maguire is one of the most beloved actors working today, and while he’s most famous for playing Spidey, his career is packed with brilliant projects.
With his famously wide eyes and cherubic face, it seems obvious that Tobey Maguire found fame early on in Hollywood as a child star, but the future Spider-Man actually had to wait a minute for take off — partially thanks to consistently losing out on roles to his old pal, Leonardo DiCaprio.
Thankfully, that slightly stunted early career development has led to a rich and varied catalogue of work — a life in the industry that’s seen the actor scale the heights of the Chrysler building as Peter Parker, and reach the depths of depravity in roles like the drug-addled James McKay in Damien Chazelle’s still underappreciated Babylon.
In the list below, you’ll find ten of the actor’s best movies, so read on to discover more and use the guide below to find out where to stream them on services like AppleTV, Netflix, Prime Video and elsewhere.
One of the first directors to make wonderful use of Maguire’s creepier side was Terry Gilliam, who cast him as a golden-haired hitchhiker in his 1998 adaptation of Hunter S. Thompson’s Fear and Loathing in Las Vegas.
The story follows Johnny Depp’s Raoul Duke and Benicio del Toro’s Dr. Gonzo on a drug-fueled bender — the kind that (similar to movies like The Hangover, but trippier) really helps to put the “Sin” in “Sin City”. Maguire’s scene is not enormous, but it’s nothing if not memorable.
Ok, so Spider-Man 3 has its haters — and probably for good reason — but honestly, this movie takes so many weird swings that I’ve always found it kind of difficult not to like.
A safer bet would have been to put Maguire’s touching cameo in Spider-Man: No Way Home in this slot, but if I have to choose — as I do, for the purpose of this list — I’m taking Raimi any day of the week. Even at his worst, he’s better than most.
After picking up a Golden Globe nomination in 2010, Maguire enjoyed a few years near the top of some Hollywood call sheets. In 2012, he landed the role of Nick Carraway, opposite his good friend Leo, in Baz Luhrmann’s big money adaptation of The Great Gatsby.
Luhrmann was the second filmmaker to bring the Fitzgerald classic to the screen, after the Robert Redford-starring version in 1974, and the Australian sensationalist approached the job with characteristic swagger and relish. If you enjoy his version of Romeo + Juliet, you’ll probably be into it.
Aside from making him a bonafide movie star, landing the role of everybody’s favourite neighbourhood webslinger also opened quite a few doors for Maguire in other areas of the movie world. Case in point was Gary Ross’ 2003 weepy true story piece, Seabiscuit — in which the actor starred as the jockey of that legendary steed.
If you like the period-set, autumnal-hued awards movies of that time (think October Sky and For the Love of the Game), you’ll probably have a lovely time with this one. Just be warned: the “Oscar bait” gets a little overused these days, but this movie really takes the — well, you know.
For all his charms and best efforts, Maguire never quite managed to make a serious splash with any of the major Hollywood awards bodies. The exception to that rule was a lone Golden Globe nomination for Best Actor – for his portrayal of a marine who’s shot down in the war in Afghanistan — in Jim Sheridan’s Brothers.
The movie also stars Jake Gyllenhaal, Natalie Portman, Sam Shepard, and a young Carey Mulligan — so if you’re a fan of any of them and appreciate Sheridan’s work from that era (think In America), it’s worth tracking down.
As the years go by, I’m starting to get the feeling that Whiplash director Damien Chazelle’s Babylon will likely be remembered as a rough diamond. This wildly ambitious attempt to capture the Wild West vibe of the early days of Hollywood ended up being a bit too ambitious and panoramic for its own good — but when this thing works, it really really works.
For an example of this, just check out the scene when Maguire’s James McKay is introduced in the third act — looking like some combination of uber-decadent Hollywood mogul and Satan; the actor’s saucer-like-eyes swollen and dilated to oblivion. Like plenty of other moments in this movie, it’s worth the entrance alone.
If you’ve already seen Seabiscuit and are looking for another autumnal Maguire classic, you really can’t go wrong with The Cider House Rules. This is the movie that won Michael Caine his second Oscar — for playing the role of Dr. Larch, who runs an orphanage in Maine during the Second World War.
Maguire stars as one of Larch’s orphans in a cast that also features Paul Rudd, Erykah Badu, Delroy Lindo, Kieran Culkin, and Charlize Theron. If you love New England-set movies about melancholy adolescents (think Dead Poets Society and The Holdovers) this is definitely a movie for you.
If we consider that everyone from Andrew Garfield, Tom Holland, Shameik Moore, Jake Johnson, Hailee Steinfeld, Daniel Kaluuya (and so many others) have spun their own unique webs as Spider-Man in the last ten years or so, it’s amazing how enduring Tobey Maguire’s early performances in the role have proved to be.
There are no shortage of origin story clichés in Spider-Man, but thanks to Maguire’s performance (alongside Willem Dafoe’s iconic Green Goblin and Kirsten Dunst’s pitch perfect Mary Jane) and Raimi’s signature directorial flourishes, Spidey’s first big screen adventure has aged incredibly well.
It doesn’t always happen that the first big break in an actor’s career also ends up being one of their finest movies — though not everyone has their first big break in an Ang Lee classic. Working from a script by James Schamus, Lee (who by that point was known for The Wedding Banquet and Sense and Sensibility) confirmed his generational ability as a shapeshifting director by absolutely nailing the story’s eerie, suburban-gothic tone.
Maguire — who was 20-years-old at the time — doesn’t exactly star as Paul Hood (the son of Kevin Kline and Joan Allen’s Ben and Elena) but he shines bright amongst the film’s ever so starry cast.
A villain/antihero for the ages in Alfred Molina’s Doctor Octopus; Sam Raimi absolutely cooking with the action sequences; a few of the most movingly heroic sequences in any Marvel adaptation — these are just some of the reasons why Spider-Man 2, Maguire’s second outing in the role, is still considered among the best superhero movies ever made.
On top of that, it basically inked the blueprint for most Marvel movies going forward. So, if you’re an MCU fan who for some reason has yet to see it, it’s never a bad time to put this one on.
