Today I embark on one of the most ambitious projects I’ve attempted during the almost nine years I’ve been posting a Song of the Day.

I was inspired by my favorite podcast, Filmspotting, which (inspired by March Madness) has run a Filmspotting Madness competition each year to determine the best [fill in the blank].

The first year they had actors face off in a bracketed competition, with Michael Fassbender taking the crown. Last year it was directors, and the Coen Brothers emerged victorious. This year they had 64 films battle it out, with The Godfather emerging as the one to rule them all.

I plan to do the same with musical artists. Specifically, 64 artists who mean something to me. Welcome to Montauk Madness!

I don’t have the audience of Filmspotting, so I can’t expect thousands of people to vote on my matchups. But I will provide polls so readers can chime in and I hope I get enough votes to make the results meaningful. If not, they’ll just reflect my own opinions and there’s nothing wrong with that.

I started with a list of 85 artists I enjoy more than a little bit, avoiding anybody with just an album or two under their belt. I narrowed that down to the 64 you’ll read about over the next several weeks. They have been paired off randomly to come up with the head-to-head matchups.

The first matchup in Round One is Michael Penn vs. Billy Joel. An easy one. While I’m a big fan of Penn’s first two albums, and found a lot to like in his next three, he certainly can’t stack up against the piano man.

Register your vote in this round below, and I’ll reveal the winner at the end of Round One.