No matter who your favorite Spider-Man is, Tobey Maguire will always be known for playing one of the many versions of the web-slinging hero, and the longest running, thanks to Spider-Man: No Way Home. He will shortly be playing a supporting role in the new Brad Pitt movie, Babylon, which will be his 15th as a producer. Over the years his boyish looks have led him to compete for roles against Leonardo DiCaprio, Leo mostly winning, but that didn’t make them rivals, and they have frequently worked on projects together. The most notable is in our list, so without further ado, take a look below at Maguire’s seven essential performances.

The Details (2011)

Who would have thought worms could cause so much trouble? Jeff Lang (Tobey Maguire) is an obstetrician-gynecologist who, along with his wife, Nealy (Elizabeth Banks), decides to lay a new lawn and expand their house in preparation for a new child. Simple. However, raccoons become attracted to worms within the grass, and those pesky critters trigger a chain reaction of accidental cat poisoning, an extramarital relationship, blackmail, and murder. Can Jeff and Nealy survive their troubles together by clearing up their lives, and those animals?

Dark, funny, and a slightly surreal comedy exploring Jeff Lang and the consequences of his thought process. Maguire plays aloof with a huge amount of natural charm, and he makes all the tragedy, somehow funny. When he wants to be, he makes a perfect straight-man.

Seabiscuit (2003)

With a financially ruined family, John "Red’"Pollard (Tobey Maguire) is sent away to live with a horse trainer. He loses the sight in one eye due to amateur boxing, but he manages to become a jockey to a small, and unlikely looking racehorse, Seabiscuit. Pollard takes up the challenge and miraculously he and the racehorse become a successful team, and inspire a nation to support the underdog. Soon, the ultimate showdown between Seabiscuit and the best racehorse of all, War Admiral, will not only create a winner, but the mood of a whole country.

Based on real accounts and indeed real accomplished racehorses, Seabiscuit is a magnificent 20th century snapshot of a country on the brink of becoming great, and needing that little something to help it along the way. An enchanting storyline with a believably accurate visual of life in the early 20th century, the movie was nominated for seven Academy Awards. Maguire worked hard to lose the pounds to play a convincing jockey, only to put them all back on for Spider-Man 2.

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The Cider House Rules (1999)

Homer Wells (Tobey Maguire) has grown up in an orphanage under the watchful eye of Dr Wilbur Larch (Michael Caine). Larch trains Wells to help out and perform abortions, but although trained, he refuses to perform them. He feels there is more to life, and when he gets the chance to leave, he moves onto a cider-orchard estate as a worker. There he begins a romance with Candy Kendall (Charlize Theron) whose boyfriend, Lt. Wally Worthington (Paul Rudd), has left to fight in World War II. As time goes by, things change drastically, Wally returns, a broken man, Homer is forced to perform an abortion, and his mentor, Larch, leaves Wells a parting gift that will change his life forever, if living life hasn’t already.

A big performance from Michael Caine that won him an Academy Award for Best Actor in a Supporting Role. A role that saw him having to drop his distinctive acerbic London accent and replace it with an American one. As a whole, the movie touches on many themes and ideas but to generalize, it’s about the rules of life and how we react to them, for better or worse. Maguire and Caine do this adaptation of John Irving’s novel justice, even if the screenplay has cut out various subplots. Still, it’s an all-round life lesson that also happens to be enjoyable.

Pleasantville (1998)

Teenagers David (Tobey Maguire) and his sister Jennifer (Reese Witherspoon) are sucked into their TV and into a black and white show called Pleasantville. There they must act as the characters Bud and Mary. It’s a perfect world where everyone excels, but it’s a world where sex and emotion don't exist. Slowly, through Bud and Mary’s actions, parts of the bubble-like world and its people begin to turn colored. The full-color people become enlightened, but are seen as a threat to the norm, and soon a ban of colored people is put in place. What have Bud and Mary done?

An original, fantasy comedy that can strike a chord across all walks of life and the problems that we all face. It celebrates the loss of innocence and the power of change while satirizing the 1950s American Dream with sanitized flair. It’s a movie that went largely misunderstood, wasn’t as successful at the box office as it should have been, but is one that is brave enough to challenge society and its false aspirations of life.

Brothers (2009)

Capt. Sam Cahill (Tobey Maguire), while fighting in Afghanistan, is presumed dead and declared KIA. His wife, Grace (Natalie Portman), and their two children are left to pick up the pieces. Sam’s brother, Tommy (Jake Gyllenhaal), starts to help Grace, even remodeling her kitchen. It’s not long before the inevitable happens, they sleep together. Tommy becomes a big hit with the children as well, but when news of Sam’s rescue arrives, the good news only brings the opposite as Sam is clearly not the man he used to be, and Tommy and Grace have to deal with Sam’s unpredictable actions.

An exceptional performance by Maguire as a soldier suffering with post-traumatic stress. A broken character who has finally arrived home to find that his family have moved on and healed, and nothing he can say or do will make it how it used to be. Maguire goes dark and deep into Sam Cahill’s persona. Brothers is definitely Maguire’s movie, and he received a Golden Globe nomination for it.

Pawn Sacrifice (2014)

East meets west, America versus the Soviet Union, and there can only be one winner. From an early age Bobby Fischer (Tobey Maguire) has immersed himself in the game of chess. He has beaten almost all that he has faced, but beating the greatest chess playing nation in the world, Russia, is going to be a very different matter. Against corruption, communism, and forced patriotism, Fischer finally secures a place in Reykjavík, Iceland, to play in the World Chess Championship against Boris Spassky (Liev Schreiber), and it’s not just chess that’s at stake.

A biographical drama that sums up the fears of America during the Cold-War era of the 1970s and draws parallels with the social paranoia, with a simple game called chess. Maguire is spellbinding and encapsulates a man who struggles with distractions while suffering from temper tantrums. Some chess inaccuracies noted, and a poor show at the box office are not enough to dampen Maguire in a tense and edgy role, and one of his best.

The Great Gatsby (2013)

Nick Carraway (Tobey Maguire), a promising writer, moves into a small cottage on the grounds next to Jay Gatsby’s (Leonardo DiCaprio) mansion. Fascinated by the wild and extravagant parties that Gatsby throws, Carraway becomes embroiled in his neighbor's fantabulous world. A world where even the guests are unsure who their host really is. Gatsby befriends Carraway and teaches him of the power of hope, but not before he learns of obsession, loss, and finally tragedy.

Based on F. Scott Fitzgerald's eponymous novel, The Great Gatsby is as lavish as the lifestyle of the subject of the story. A $100 million budget glamorizes the Roaring Twenties like no other. DiCaprio and Maguire share a great onscreen partnership, filling the shoes as master and pupil with ease. Like most adaptations of older novels, some of the more sensitive elements have been omitted or toned down. There are plot changes to the book, but regardless if you love F. Scott Fitzgerald, you have to take your hat off to Baz Luhrmann’s visually stunning direction. A rip-roaring, 20s, spectacle of intrigue, mystery, and drama.