Strong Sad's iPod
From Homestar Runner Wiki
The iPod is a portable music player Strong Sad is seen with that has Strong Bad's "Song About Sibbie" on it. It was 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 or second-generation Apple iPod classic; it can not possibly be a third-generation iPod (which would have four buttons horizontally under the screen) or an iPod from a generation produced after the release of sibbie. Additionally, since "Songs" appears on the screen instead of "Browse," it is probably running iPod software version 1.5 or newer.
In 2006, a different, fifth-generation iPod was seen on the Podstar Runner page, next to the Floppy Disk Container. Strangely, this video iPod has the headphone jack located at the top center, while the real fifth-generation has the jack at the right.
In the email environment, Strong Sad is shown with a new MP3 player. This new one strongly resembles an Apple iPod touch (since Strong Sad refers to it as an MP3 player and not a cell phone) with its black case and touch screen for navigation. This same iPod appears on the 2008 version of the Podstar Runner page.