The songs:

• Fast Car - Tracy Chapman
• Hey Ya! - Outkast
• Tennessee Whiskey - Chris Stapleton
• Fell On Black Days - Soundgarden
• The Boxer - Simon & Garfunkel
• Master Blaster - Stevie Wonder
• Little Wing - Jimi Hendrix
• I'll Be - Edwin McCain
• Old Man - Neil Young
• You Are The Best Thing - Ray LaMontagne

Why these songs?

First & foremost because they're great songs.

But specifically why these great songs and not some other great songs?

Because these ones let us dive into all kinds of thing you oughta know:

• Fast Car -> tuning down a song that was capo'd up
• Little Wing -> tuning up a song that was recorded on a detuned guitar
• Tennessee Whiskey -> 6/8
• I'll Be -> 3/4
• Fell On Black Days -> 6/4
• The Boxer -> cut time
• Hey Ya -> mixed meter
• Master Blaster -> slowing down tricky passages

etc etc etc

This is just the beginning

You'll use these songs to learn the SongOS operating system.

From there, you can use this operating system learn any song that catches your ear.

(It's what I do!)