SockPerson

Aww dude. I love The Shaggs. Their music is quirky, sincere, and just plain heartwarming. They're the epitome of unpretentiousness and heart in music.

Here's a great quote from shaggs.com:
It's true; saying they aren't great musicians is an extreme understatement. They can't play for sh*t. But I'll be damned if The Shaggs don't bring a smile to my face every time.

Normally, I wouldn't recommend The Shaggs, because not a lot of people get it. But if you can understand what they are, then it might just change and challenge any past perceptions of ability, and talent you may have had.

I think liking outsider music in general is going to brand you a pretentious d-bag in someone's eyes eventually.