I kept ruling out Miles Davis because you said it wasn't blues. Then I remembered Miles is jazz Miles Davis - Kind of Blue So What Freddie Freeloader All Blues Blue In Green Flamenco sketches Great Clues! Great album!
Another clue. Concentrate on picture 2. What's a word for someone who never pays for anything that goes well with the first name of that person? Edit: Never mind! You got it!
I have one that I was going to abandon because I thought it was too hard, but I have the pics if you're up for a challenge. Everyone's invited.
I've seen picture 5 before, I'm sure, but I only now realized, wait, that's not how mirrors work! Is it a song with "Mama" in the title? (It's not Genesis, anyway.)
Bob Seger, "Beautiful Loser" almost works: title track for the fired teacher (were you giving me a clue earlier?), "Black (K)night", "Travelin' Man", and "Momma" for the last one. Can't see a song for the 4th photo. Oh wait, "Katmandu" = Cat + man + Dew! Now that is tricky!