"Weird Al" Yankovic

This first edition of Weird Al's greatest hits came out in 1988, but the parodies are such familiar songs of their times that people of any age can appreciate them. Of course, his best-known parodies ("Fat" and "Eat It") are here, but there's also Al's mutation of Madonna's "Like a Virgin" into "Like a Surgeon," his transformation of James Brown's "Living in America" to "Living with a Hernia," and his spin on Ritchie Valens' "La Bamba" ("Lasagna"). In addition to the song parodies, there's also one of Weird Al's best "style parodies" in "Dare to Be Stupid," where he jocks the sonics of Devo while singing lines like, "Stick your head in the microwave and get yourself a tan."