Launch date: September 7, 2005

Fatal flaw(s): Underpowered, difficult to upload songs and operate, limited storage space

Meet the original iPhone. Before Apple set out to design its own handset, it opted to partner with the most popular mobile phone maker in the game (at the time)—Motorola—on the ROKR E1. Basically a re-badged Motorola handset, the ROKR showed Apple that this was not the most ideal way to give customers access to their iTunes library on their phones. Due to firmware restrictions, users couldn't have more than 100 songs uploaded at any given time. Uploading songs proved to be painfully slow, and the newly released iPod Nano gave customers looking for a super-portable iPod, a super-portable iPod. The two companies parted ways and the rest is history.