If you were living out your dream as a successful rising artist, it seems like it would be pretty tough to narrow down the highlight of your career. We sat down with Betty Who, Crystal Fighters, and more and put them to the test. These artists have done it all, from writing with longtime heroes to performing in front of President Obama (*sigh*). Not everyone's best moment is a big one, which might come as a surprise. Sometimes it's a random show in the middle of nowhere that feels the most special.