the Brak song "I Like Hubcaps" from the album: Brak Presents the Brak Album Starring Brak. In the song, Brak says: "I like pineapple upside-down cake, why's it upside-down? WHY'S IT UPSIDE-DOWN?"
In the first episode of The Jetsons (Rosey the Robot, Sept. 23, 1962), Rosey clobbers Mr. Spacely with a pineapple upside-down cake after he makes an insulting comment. Spacely then fires George, but later calls from a pay phone and offers him his job back after tasting the cake - which he is still wearing on his head.