Song of the Day #3,268: ‘Brand New Day’ – Sting vs. Paul Simon

Sting and Paul Simon lived in the same New York apartment building in the 80s, and collaborated on a concert tour in 2014. Now they come together again for a Montauk Madness Round Two death match.

Much to my chagrin, Sting defeated Sinead O’Connor in Round One rather easily, earning 70% of the vote. Paul Simon, surprisingly, had an even easier time dispatching Elton John, with 73%. Continue reading

Song of the Day #3,267: ‘Gone For Good’ – The Shins vs. Lucinda Williams

None of the Round Two Montauk Madness matchups have been laughers so far, but this is the first one I’ve found truly difficult.

Lucinda Williams advanced easily over Garbage, picking up 91% of the votes, while The Shins won in more of a squeaker, besting Coldplay with 55%. I voted for both of them in those battles. But who should I vote for here? Continue reading

Song of the Day #3,266: ‘Solsbury Hill’ – Peter Gabriel vs. Van Morrison

Our next Round Two contestants are around the same age and have each been recording for five decades, making for a nice heavyweight matchup.

Peter Gabriel defeated Josh Rouse in Round One, picking up 67% of the vote. Van Morrison has an even easier time, dispatching Barenaked Ladies with 91%. Continue reading

Song of the Day #3,265: ‘She’s Got a Way’ – Billy Joel vs. Frank Sinatra

OK, now it gets interesting! Welcome to Round Two of Montauk Madness. The 32 artists who survived Round One now advance to face each other in a battle to reach the Sweet Sixteen.

Both Billy Joel and Frank Sinatra cleared Round One without breaking a sweat. Joel received 95% of the vote in a matchup against Michael Penn, while Sinatra picked up 86% against my beloved Tift Merritt.

How will they fare against each other? Continue reading

Song of the Day #3,259: ‘Vicar in a Tutu’ – The Smiths vs. Ben Folds

At long last, here we are at the final matchup of Round One of Montauk Madness! Thirty-two battles to determine which 32 artists will advance to fight again.

Both of today’s contenders have shown up already in Round One in other incarnations: The Smiths’ frontman Morrissey showed up as a solo act, while Ben Folds showed up in the form of his band, Ben Folds Five.

Continue reading