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.

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Song of the Day #3,258: ‘Chantaje’ – Shakira vs. The Beatles

I can’t pretend there’s any suspense in the penultimate Round One matchup in Montauk Madness. As much as I enjoy Shakira’s work, especially in her native Spanish, she ain’t putting up a fight against The Beatles.

Of course there is no shame in losing to the Fab Four. And this blog post led me to the discovery that Shakira just released a new album, El Dorado, which I promptly downloaded. So it’s really a win for her.

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Song of the Day #3,255: ‘Twilight’ – Elliott Smith vs. Lyle Lovett

Today’s Montauk Madness first round matchup is one of the hardest to date. The beautiful melancholy of Elliott Smith against the wry virtuosity of Lyle Lovett. One man whose career was cut tragically short by suicide and another who seems to have stopped recording new music altogether after a brilliant decade-long run from 1986-1996.

What exactly happened to Lovett after the ’96 release of The Road to Ensenada, his best album? He released seven albums over the next 20 years, almost all of them covers albums.

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Song of the Day #3,254: ‘My Hometown’ – Bruce Springsteen vs. John Mellencamp

At first blush, today’s Montauk Madness matchup has a student vs. master dynamic. Early in his career, John Cougar was viewed as a poor man’s Bruce Springsteen.

But John Mellencamp has carved out quite the career in the four decades since his debut. In fact, he’s released five more albums than Springsteen in three fewer years, and spanned a variety of styles along the way.

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Song of the Day #3,253: ‘Without a Fight’ – Brad Paisley vs. Lana Del Rey

Brad Paisley vs. Lana Del Rey seems like an entirely left-field matchup in Montauk Madness, but given Paisley’s track record of collaboration, I would not be at all shocked if these two paired up on his next album.

Paisley was the first true country artist I loved, a journey I chronicled in this blog entry after the release of American Saturday Night. That album and the few that preceded it are all classics of the genre.

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Song of the Day #3,252: ‘The Ocean’ – Dar Williams vs. Fiona Apple

Just yesterday I was discussing the tough road female artists have had in Round One of Montauk Madness, thanks to the luck of the draw in the matchups. Here’s another example, where two very talented women have to face off against each other (the first such battle, unless you count Lucinda Williams taking on the Shirley Manson-led Garbage).

Dar Williams is a relatively obscure artist who has quietly released almost a dozen albums of literate folk pop. She is a master lyricist and knows her way around a melody, and she’s responsible for one of my very favorite songs, ‘When I Was a Boy.’

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Song of the Day #3,251: ‘Louisiana 1927’ – Randy Newman vs. Adele

Women have faced an uphill battle in this first round of Montauk Madness, going up against the likes of Frnak Sinatra, Bob Dylan, Tom Petty, David Byrne, Elvis Costello and Ben Folds Five. Here’s another example, as the talented and mega-successful Adele faces off against one of our greatest songwriters, Randy Newman.

I feel bad for Adele, who I like both as an artist and a personality, but this is an easy call for me. Newman is a unique and special talent who deserves to go far in this contest.

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