Ask Ty...December 9 [The Best Descriptive Songs Question]

It must be Tuesday Wednesday, Middlespace Cadets, because I'm answering your questions

Q: Dear Ty,
What five songs best describe you?

- Grayman
Ty: Good question and an even better observation, Grayman. You're a lucky fella because I immediately deleted that email when it first arrived because I declared it a silly question; too contrived and theoretical. But I later fished it out of the wastebasket because there was something intriguing about it, as an exercise; the process to determine such findings. Besides I'm all about the contrived and the theoretical. So, I apologize for being so reactive, Grayman. My bad, H. Sometimes I'm an asshole.

What are the five songs that best describe me, huh? Not my favorite songs. Or most cool or obscure songs. Not best engineered or performed songs. I mean just five songs...that's nearly impossible. But I can try. I've done lists of most influential artists (with a sampling of songs) in the past and that exercise resulted in like 80 artists split across four decades:
Part I
Part II <-- just go here
Part III
But Five Songs that "best describes me" is something entirely. So, Grayman, I accepted your challenge.

It took me several days to take this first step and I have narrowed it to 20. I don't think I can winnow any farther. But I came up with twenty songs that I believe "best describe me." Some are selected for the words in the title (but are great songs nonetheless), some are picked for words in the lyrics, and others are definitely in for THE SONG itself and my relationship with that song. How's that?

Here are the 20 - 5 per personality (and I do not need to know if a link doesn't work - no guarantees on that):
  1. Adventures In Failure > MC 900 Ft. Jesus > Welcome To My Dream
  2. American Gangster > Jay-Z > American Gangster
  3. Character Zero > Phish > Billy Breathes
  4. Chris Michaels > The Fiery Furnaces > Blueberry Boat
  5. Coma > Guns N' Roses > Use Your Illusion I
  6. The Day I Tried To Live > Soundgarden > Superunknown
  7. Do You Wanna Get Heavy? > The Jon Spencer Blues Explosion > Acme
  8. Exaggerated Joy > Busdriver & Radioinactive > The Weather
  9. Free Radicals > The Flaming Lips > At War With the Mystics
  10. I Got the Blues > The Rolling Stones > Sticky Fingers
  11. I'm Slowly Turning Into You > The White Stripes > Icky Thump
  12. If You Have To Ask > Red Hot Chili Peppers > Blood Sugar Sex Magik
  13. Many Shades of Black > The Raconteurs > Consolers of the Lonely
  14. Paper Planes > M.I.A. > Kala
  15. Roses Are Free > Ween > Chocolate And Cheese
  16. Strange Apparition > Beck > The Information
  17. Thank You For Talkin' To Me Africa > Sly Stone > There's A Riot Goin' On
  18. Voices Inside My Head > The Police > Zenyatta Mondatta
  19. We Who See the Deep > The Black Crowes > Warpaint
  20. You See Me Crying > Aerosmith > Toys In The Attic
How 'bout you guys pick what best describes me. Why I gotta do all the hard work anymore? These were selected from the 5,000+ songs on my computer. I can't pick five, Grayman. I am a failure!

The end. Just a guess,