18) Tobey Maguire in Tropic Thunder (2008)

While Tom Cruise's surprise appearance in Tropic Thunder is what many people consider the film's best cameo, it technically isn’t a cameo at all. With an impressive 10 minutes of screen presence and an important role in the plot, Cruise's Les Grossman is truly a supporting character. Therefore, the movie's finest cameo is actually Tobey Maguire. The Spider-Man actor shows up as himself in a mock movie trailer for Satan's Alley, where he gazes flirtatiously at the award-winning "actor" Kirk Lazarus (Robert Downey Jr.)
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Edited by Apoorva Jujjavarapu