Strong Sad's iPod
From Homestar Runner Wiki
A portable music player Strong Sad is seen with. It has Strong Bad's "Song About sibbie". It was also one of Strong Bad and The Cheat's Stolen goods in Strong Bad Is in Jail Cartoon. The device has been identified as a first-generation Apple iPod. (A second-generation iPod would read "Browse" on its main menu instead of "Songs", as well as a different wheel and button layout. Also, a fourth-generation would not have the buttons outside the click wheel.)
