Tobey Maguire – 10 Best Movies

By Vlad Zakh · April 13, 2026

Spider-Man remains the role most people know him for, and the trilogy still holds up as the foundation of the modern superhero genre, while Seabiscuit and The Cider House Rules show a quieter, more restrained side. Brothers returns a presumed-dead soldier home changed, Wonder Boys orbits Michael Douglas’s blocked novelist, The Great Gatsby makes him Nick Carraway, and Babylon adds a supporting role during Hollywood’s transition to sound. Pleasantville and Spider-Man: No Way Home round out the list.

Babylon (2022)

TMDB ★ 7.3

Ambitious dreamers deal with the hedonistic excess and brutal transformation of 1920s Hollywood.

Directed by Damien Chazelle · 3h 09m · Rated R

Where to watch

Stream: Hulu, Paramount Plus Premium, Paramount Plus Essential, Paramount+ Amazon Channel, Paramount+ Roku Premium Channel · Rent: JustWatch TV, Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Brothers (2009)

TMDB ★ 7.3

A soldier presumed dead comes home forever changed.

Directed by Jim Sheridan · 1h 45m · Rated R

Where to watch

Stream: Amazon Prime Video, Amazon Prime Video with Ads

▶ Trailer Letterboxd

Wonder Boys (2000)

TMDB ★ 6.8

A blocked novelist and creative writing professor navigates personal chaos over one eventful weekend.

Directed by Curtis Hanson · 1h 47m · Rated R

Where to watch

Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

The Great Gatsby (2013)

TMDB ★ 7.3

A mysterious, self-made millionaire's lavish parties hide his obsessive pursuit of a lost love.

Directed by Baz Luhrmann · 2h 23m · Rated PG-13

Where to watch

Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Pleasantville (1998)

TMDB ★ 7.3

Tobey Maguire plays a modern teenager transported into a black-and-white 1950s sitcom world.

Directed by Gary Ross · 2h 04m · Rated PG-13

Where to watch

Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

The Cider House Rules (1999)

TMDB ★ 7.1

Delroy Lindo appears as an orphan raised by a small-town doctor learns his mentor's trade before venturing out into the world.

Directed by Lasse Hallström · 2h 06m · Rated PG-13

Where to watch

Stream: fuboTV, MGM+ Amazon Channel, Philo, MGM Plus Roku Premium Channel, MGM Plus · Rent: JustWatch TV, Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Seabiscuit (2003)

TMDB ★ 7.1

An undersized racehorse becomes an unlikely Depression-era symbol of hope.

Directed by Gary Ross · 2h 21m · Rated PG-13

Where to watch

Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Spider-Man: No Way Home (2021)

IMDb ★ 8.1 RT 93% Metacritic 71

A spell gone wrong pulls villains from other universes into Peter Parker's already fractured world.

Directed by Jon Watts · 2h 28m · Rated PG-13

Nominated for 1 Oscar35 wins & 72 nominations

Where to watch

Stream: Disney Plus, fuboTV, YouTube TV, FXNow, Starz Apple TV channel · Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Spider-Man 2 (2004)

IMDb ★ 7.5 RT 93% Metacritic 83

Peter Parker's double life as Spider-Man collides with a new, tragic supervillain.

Directed by Sam Raimi · 2h 07m · Rated PG-13

Won 1 Oscar25 wins & 60 nominations

Where to watch

Stream: Disney Plus, Hulu, fuboTV, YouTube TV, FXNow · Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Spider-Man (2002)

TMDB ★ 7.4

The Green Goblin, still one of the more genuinely unhinged superhero-movie villains.

Directed by Sam Raimi · 2h 01m · Rated PG-13

Where to watch

Stream: Disney Plus, Hulu, fuboTV, YouTube TV, FXNow · Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Plex · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Streaming availability data from JustWatch, via TMDB. Availability changes often, so check the service before you plan a movie night.

Vlad Zakh

Founder, Movieix

Founder of Movieix. He started the site because most recommendation pages felt like noise. Here, lists are sorted by who's in the film, where it's from and what mood you're in tonight.

Tobey Maguire – 10 Best Movies

Babylon (2022)

Brothers (2009)

Wonder Boys (2000)

The Great Gatsby (2013)

Pleasantville (1998)

The Cider House Rules (1999)

Seabiscuit (2003)

Spider-Man: No Way Home (2021)

Spider-Man 2 (2004)

Spider-Man (2002)

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