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The best art can only come from experience, but if you make it obvious you're singing about yourself, you're boasting.
When Yngwi Axegrinder left his mountainhome as a young musician, it was to collect tales of daring adventures: he wanted to see the world outside, and have something real to sing about. He found a group of adventurers who loved the idea of having the bards sing their praises, and they allowed him to travel with them. They were not very good at protecting their musician, so he had no choice but to learn how to fight... poorly. When the group decided to pick a reckless fight with a red dragon, everyone was killed - except for Yngwi. The dragon was so amused by the idea of adventurers traveling with a musician who couldn't even hold his own in a fight, that he imprisoned Yngwi in his lair to sing songs about him instead.
While imprisoned, Yngwi had nothing better to do than to study the musical arts, and the dragon was happy to supply him with everything he needed to "make better music about Fretanth the Firestarter's greatness." As a result, he came to a deeper understanding of the nature of the Universe: the entirety of Creation was music, and by hitting exactly the right notes, he could bend reality to his will. His will was to slip out of the dragon's lair, undetected, as if by magic - so, he did. And returned later with a more skilled crew of adventurers to slay the dragon and make a pair of sweet boots out of his hide.
He is prone to wild and reckless plans, but protective of his crew. He wants to be known for his art, not for the deeds that allowed him to create it. Fortunately, he is currently stuck on a different plane of existence accompanied by some strangers he'd only just met, so tales of the personal role he played in his current adventures are unlikely to reach home... Assuming he can manage to reach home himself to sing about them, of course!
