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2 of 10 Credit: Motorola

Motorola Rokr E1

In an effort to keep up with the enthusiasm that the tech crowd had for the Apple iPod, Motorola leaped with both feet onto the bandwagon with the Rokr E1, a phone with an officially licensed Apple iTunes music player built in, but with the deal-breaking restriction of only being allowed to store 50 songs at a time. Released in 2005, the Rokr E1 hit stores at about the same time that Apple launched the iPod Nano, a smaller device capable of storing up to 4GB of music. Apple's execs must have laughed all the way to the bank after Motorola's team signed on the line for this licensing agreement.