Song of the Day #3,231: ‘With Or Without You’ – U2 vs. David Bowie

Our next Montauk Madness matchup pairs two legends, one who sadly (and triumphantly) passed away last year and another struggling to remain relevant after spending the better part of four decades as the world’s greatest rock band. David Bowie vs. U2.

Had I faced this decision before Bowie’s passing, I likely would have gone with U2. Apart from the hits, I knew Bowie’s work mostly by reputation. Of course, Bowie’s hits alone put him in contention, but I own almost all of U2’s albums and consider them at worst enjoyable and at best masterpieces (The Joshua Tree remains one of the seminal listening experiences in my life as a music fan).

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Song of the Day #3,230: ‘Hanginaround’ – Counting Crows vs. Morrissey

Entering our third week of Montauk Madness, ten first round mathcups have been posted with 22 to go. I’ll leave all of the polls open for the duration of this round to pick up any stragglers. All of the Round One matchups can be accessed here.

The seeding in this tournament was determined randomly, and it’s fun to see the interesting pairings that result. Today’s battle, for example, is a showdown between depressed whiners Adam Duritz and Morrissey — specifically Counting Crows vs. Morrissey’s work as a solo artist.

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Song of the Day #3,227: ‘Money’ – Pink Floyd vs. Vampire Weekend

Our next Montauk Madness matchup is a battle across the decades, pitting a 70s powerhouse against an innovative indie band from the past decade. I give you Pink Floyd vs. Vampire Weekend!

My high school self would have had no problem with this choice, as I pretty much lived and breathed Pink Floyd in those years (not to mention that Vampire Weekend’s Ezra Koenig was in pre-K).

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Song of the Day #3,226: ‘I Should’ve Known’ – Aimee Mann vs. Ben Folds Five

OK, here’s the first matchup in Round One of Montauk Madness that hit me right in the gut: Aimee Mann vs. Ben Folds Five.

Why hurt me like this, oh musical gods, by pitting two of my all-time favorite artists against each other in what should be the easiest round?

I discovered both of these acts right around the same time, 20 years ago. I know that because I gave their latest CDs (Mann’s I’m With Stupid and BFF’s Whatever and Ever Amen) to my brother-in-law as a birthday present in 1997.

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Song of the Day #3,225: ‘Fields of Gold’ – Sting vs. Sinead O’Connor

Stepping into the ring for the next Montauk Madness battle are a couple of iconic figures from across the pond. Sting (but not The Police) vs. Sinead O’Connor.

Neither of these artists is a slam dunk favorite of mine, but both have put out music I absolutely adore. And both have trailed off later in their careers, making this more of a nostalgia pick.

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