Not Spider-Man, Kate Winslet Called Tobey Maguire’s Weirdest Role in a Tom Cruise Movie His Crowning Achievement

Many may have missed Tobey Maguire’s brief cameo in the star-studded satirical comedy Tropic Thunder, but not Kate Winslet. Maguire appeared in a fictional movie trailer within the film, co-starring alongside Robert Downey Jr.’s Kirk Lazarus. When Maguire encountered Winslet after the role, the Titanic actress stated that the film was Maguire’s crowning achievement.

Maguire wondered whether it was a compliment or not, but for that reason, he chose to preserve Tropic Thunder for posterity when asked by fans. The film turned out to be a surprise hit upon its release in 2008, grossing $195.7 million at the box office.

Also Read: “How do we make it more exciting?”: Tobey Maguire Promised a “Different” Spider-Man 4 That Never Happened

The Role That Earned Tobey Maguire A Compliment From Kate Winslet

Tobey Maguire played himself in Tropic Thunder, appearing in a fictional movie trailer for Satan’s Alley. Since the release of the film, fans have clamored for an actual Satan’s Alley featuring Maguire and Robert Downey Jr., underscoring the impact of Maguire’s brief appearance. While his actor-playing-homosexual-priest character stands out as one of his weirdest roles, the Spider-Man actor has apparently gained a celebrity fan through this role.

During a Reddit AMA session from a year ago, Maguire was asked about the film that he would want future generations to remember him by. While Maguire has a diverse portfolio of impressive roles, including Spider-Man, he went for an unexpected answer. He responded with Tropic Thunder and provided a perfect explanation for this choice.

The Babylon actor revealed that he had only worked for a few hours on Tropic Thunder. However, when he ran into Kate Winslet after the film’s release, The Holiday actress hailed his role as his “crowning achievement.” While Maguire wasn’t certain whether she meant it as a compliment or criticism, he took it positively, leading him to choose the film to be “preserved for posterity”.

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The scene featuring Downey Jr. and Maguire in the film was intended as a satire on films like Ang Lee’s Brokeback Mountain and the duo’s earlier film Wonder Boys. Interestingly, the trailer also mentions The Great Gatsby actor’s MTV Movie Award for Best Kiss, which he actually received for his upside-down kiss in Spider-Man.

Also Read: Amid Tobey Maguire Return Rumors, Avengers 6 Reportedly Commits Grave Mistake That Doomed Twilight

Tobey Maguire Was Not The Only Celebrity Cameo In Tropic Thunder

The film, directed by Ben Stiller, featured the most funny and unlikely ensemble cast, with Stiller in the lead role alongside Jack Black, Brandon T. Jackson, Jay Baruchel, and Danny McBride. The film saw a plethora of cameos and extended appearances from famous actors. Tom Cruise and Matthew McConaughey famously took on the roles of producer Les Grossman and his extremely devoted agent Rick Peck, respectively.

While Cruise and McConaughey stood out as the most prominent cameos, several others, including Martin Lawrence, Jason Bateman, Sean Penn, Alicia Silverstone, Jennifer Love Hewitt, and Tyra Banks, played small roles in the film. Stiller’s wife and actress Christine Taylor, along with the film’s co-writer Justin Theroux, also appeared in brief roles.

Also Read: The Tom Holland Spider-Man Movie That Beat Tobey Maguire, Andrew Garfield Proves MCU Still Has a Lot of Steam Left

While Maguire’s role could have sparked controversy, the film had to deal with even more pressing and controversial issues, like Downey Jr.’s blackface and the depiction of disabled people. Tropic Thunder is now available for streaming on Paramount+.