Tobey Maguire, Andrew Garfield, Tom Holland, and Shameik Moore in What to Watch (2020)

Tobey Maguire, Andrew Garfield, and Tom Holland in Spider-Man (2019)

Kirsten Dunst and Tobey Maguire in Spider-Man (2002)

Reese Witherspoon and Tobey Maguire in Pleasantville (1998)

Joan Allen, William H. Macy, J.T. Walsh, Reese Witherspoon, Jeff Daniels, Tobey Maguire, Marissa Ribisi, James Keane, and Natalie Ramsey in Pleasantville (1998)

Jeff Daniels and Tobey Maguire in Pleasantville (1998)

Joan Allen and Tobey Maguire in Pleasantville (1998)

Tobey Maguire and Don Knotts in Pleasantville (1998)

Tobey Maguire and Marley Shelton in Pleasantville (1998)

Tobey Maguire and Stan Lee in Spider-Man 3 (2007)

Tobey Maguire and Aimee Brooks in Great Scott! (1992)

Tobey Maguire and Nancy Lenehan in Great Scott! (1992)

Tobey Maguire in Saturday Night Live (1975)

Tobey Maguire, Forest Whitaker, Marion Cotillard, and Eiza González in 2068: The Going-Away Party (2023)

Leonardo DiCaprio and Tobey Maguire in The Great Gatsby (2013)

Kirsten Dunst, Alfred Molina, and Tobey Maguire in Spider-Man 2 (2004)

Charlize Theron, Michael Caine, and Tobey Maguire in The Cider House Rules (1999)

Leonardo DiCaprio, Tobey Maguire, Marissa Ribisi, Amber Benson, Scott Bloom, Kevin Connolly, Jenny Lewis, and Meadow Sisto in Don's Plum (2001)