In 2002, "Boss of Me" won the band their first Grammy Award, in the category of Best Song Written for a Motion Picture, Television or Other Visual Media.

The song was originally written with the chorus "Who's gonna guess the dead guy in the envelope" for a contest presented by the Preston and Steve show during their Y-100 days.

The box goes into Dewey's backyard where Malcolm is raking leaves, their father, Hal, is cooking on a barbecue, and Reese is using hedge clippers on a tree.

Reese spots him and, while using the weed whacker, launches him onto the grill where Hal accidentally eats him, much to Dewey's shock.

Later, the John Linnell toy is placed in a model airplane that is launched across the street before curving back and landing on the driveway.

The ska-punk band Less Than Jake covered the short televised version of the song for their album TV/EP.