The 1999 MTV Movie Awards featured notable nominees like Adam Sandler, Liv Tyler, Chris Tucker, and Jennifer Love Hewitt, representing the pinnacle of turn-of-the-millennium American pop culture. A standout moment for teenage cinephiles was a series of skits by “the Max Fischer Players,” directed by Wes Anderson. These skits humorously reimagined three nominated films: Out of Sight, The Truman Show, and Armageddon as performed by the cast of Rushmore.