Tournament of Singer-songwriter Heavyweights

Back when I was really passionate about music, before I settled down to just passionate, I'd always considered Leonard Cohen and Dr. John to be among the best at what they do—write and make music, singer-songwriters. They were in the category of the best of the best, right below Dylan and Tom Waits, next to Van Morrison, Paul Simon, Lou Reed, Lyle Lovett, Eric Clapton, Joni Mitchell, Tom Petty, Bruce Springsteen, and Neil Young. 

This list was for the living and iconic; Brian Wilson, Jim Morrison, Chuck Berry, and Buddy Holly have been dead, and so have Roy Orbison and Bo Diddley; the Stones and Beatles don't fit into this category. I have never been able to distinguish a true top between Dylan and Waits, and still can't. They are very different and very original. I always separated Cohen and Dr. John from the others because they are out of the limelight somewhat, more offbeat, more unique, with Lou Reed clinging to them because of that factor. So my favorite singers were kind of tiered that way. 

I decided to pit Leonard Cohen against Dr. John, to determine a true Number Two, with Dylan and Waits as 1a and 1b. I thought it would be a grueling battle, Dr. John carrying with him the essence of New Orleans, voodoo, and that skull and piano, Cohen with his poetry, his way with words, his literary awards and sexual innuendos. The battle wasn't even close. Cohen won easily.

The way it worked: Each got five songs. I would collect five from each, those that best represented their work. After each had five, I'd make a top ten list, and whoever seemed to dominate the list would win. I thought it would be very close. It wasn't. So I started thinking about Lou Reed versus Dr. John; that was closer, but Dr. John won. So he is three, with Reed and Van Morrison fighting for the fifth spot. Paul Simon, Eric Clapton, Lyle Lovett, and Joni Mitchell round out the top ten in that order, Tom Petty, Bruce Springsteen and Neil Young were left on the outside looking in; I know they are devastated.