Microsoft Windows 1.0!!!
Zune doesn't look too bad, though.
I had an IT job at age 15 in a large insurance company. They had a back-room we called "the arsenal" containing abandoned tech decades older than myself. While piddling through the room and found a box about 36" wide, 12" tall, and 36" deep. A closer inspection yielded a blue plastic device as large as the box containing it, with capacious black front panel dotted with indicator lights, but few controls. On the back was a phone plug-in and some sort of interface plugin about 3 inches wide. In it were three very-large circuit boards arrayed with large electronics on both sides, positioned like a giant sandwich with a big-blue commercial wrapper.
The manual lay underneath the leviathan. It was a 300 baud modem