The easiest way to get around the nasty DRM that stops you from sharing your music is with a headphone splitter that lets two people listen to the same device. And it gets even easier with a pair of these Duobuds, which feature an extra headphone jack built-in.
Available in two gender-role-reinforcing series—BFF for girls and Mates for boys—the earbuds run about $41 a pair and connect together with a Lego-like stud system to prevent them from getting all tangled up. And while you can in theory connect as many together as gravity permits, the splitters aren't amplified, so the sound quality will certainly degrade as the chain gets longer and longer. Besides, how are that many people going to agree what to listen to?