Reddit reviews Kanye West Owes Me $300: And Other True Stories from a White Rapper Who Almost Made It Big
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Two of my favorites of similar themes -
So You Wanna Be a Rock & Roll Star by Jacob Slichter (Semisonic's dummer)
Kanye West Owes Me $300 by Jensen Karp
Not quite totally in the pop genre but two memoirs I really enjoyed as someone who plays music. The Semisonic one is about a one hit wonder (on the pop charts at least) and Kanye West Owes Me $300 is about a never was but they were really good memoirs on the music business from a personal perspective. And they both show the ups and the downs but it's not all dark at all, I thought both books were pretty hilarious (especially Karp's) and they were both quick reads. So they're both not totally pop but if you're interested in what it's like to be a professional musician I would definitely recommend.