Lyric discussion by harrizonn 

Cover art for Little Wig lyrics by Ariel Pink's Haunted Graffiti

This song is based on the phrase "flip your wig" which one would exclaim if they had seen something very exciting like "when she has her surprise birthday party, she is going to flip her wig!" When you flip a little wig though, it's just a small surprise. Probably Ariel Pink's Dad was going to give him a surprise birthday party but he found out(?) beforehand, so it wasn't as much of a surprise.

Um, no? "Bigwig" is a pejorative expression for an important person. In this case Big Wig is the owner of a business or something ("My daddy works for no one"), and Little Wig is his son who's supposed to follow in his footsteps, but doesn't feel too fit for the task ("The shoes he wear don't fit, they're just too big for me"), and eventually leaves to pursue his dreams.

@harrizonn awesome