Hi Scott,
Great list! Many of my favorites appear on your list. Dianna Krall does a great job with "Boulevard of Broken Dreams", but I prefer Billy Eckstein's rendition because of his very rich voice and big band.
Your point that most people's favorites were formed during their teen and early adult years is certainly true in my case. I grew up in the 30s and 40s, became a young adult in 1950, so my taste in music is still the music that was written and played during that period. Country music has always been a favorite. Hank Williams Sr. is my all-time favorite country singer/writer. I played a barely acceptable country guitar in my teen years. My brother and our friends and I used to sit around singing Cold, Cold Heart, the Lovesick Blues and all of Hank's great songs. What wonderful memories!
If I have some time to spare next week I will try to come up with my list of favorites. Take care.
Best Wishes,
Chuck