Happy Birthday Tobey Maguire: 7 Must-Watch Movies Beyond Spider-Man .

BY SANDHYA | 21 JULY 2025

The Great Gatsby (2013)

Tobey stars as Nick Carraway in this visually stunning adaptation of F. Scott Fitzgerald's novel, alongside Leonardo DiCaprio.

Seabiscuit (2003)

He plays Red Pollard, a jockey in this inspiring Depression-era sports drama based on a true story.

Brothers (2009)

A haunting psychological drama where Tobey plays a Marine returning from war, facing trauma and family tension.

Pleasantville (1998)

He and Reese Witherspoon are teens sucked into a 1950s TV world, in this imaginative, award-winning dramedy.

Wonder Boys (2000)

Tobey shines as a troubled writing prodigy opposite Michael Douglas in this underrated literary dramedy.

Pawn Sacrifice (2014)

A gripping portrayal of chess genius Bobby Fischer, showcasing Tobey’s intensity and range.

The Cider House Rules (1999)

In this Oscar-winning drama, he plays Homer Wells, an orphan trained to be a doctor by Michael Caine.