Song of the Day #3,245: ‘Hell Yes’ – Beck vs. John Mayer

Our next Montauk Madness matchup pits somebody it’s very cool to like against somebody it’s very uncool to like. Beck, meet John Mayer.

I’m a big fan of both of these guys, so I’ll try to keep the hipness factor out of my vote. I realize that appreciating John Mayer is not great for my street cred, but I think anybody who dismisses his musical chops or his songwriting ability is mistaken. Sure, the guy can be a smug prick and some of his songs veer too close to maudlin, but so many more are spot-on.

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Song of the Day #3,244: ‘Warm Blood’ – Carly Rae Jepsen vs. Elvis Costello

The latest Montauk Madness Round One matchup features a prime contender for the whole title (Elvis Costello) vs. a newcomer with only a couple of albums under her belt (Carly Rae Jepsen). Not exactly a fair fight.

But Jepsen is a talent, no question. She might not be Rocky Balboa taking Apollo Creed to 15 rounds and losing by judge’s decision, but Costello is definitely in the other corner having taken a solid shot to the eye, nodding her way and saying “You have great things ahead of you, kid.”

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Song of the Day #3,243: ‘Tennessee Whiskey’ – Chris Stapleton

I last featured this song about a year and a half ago, when I posted a live Country Music Awards performance by Chris Stapleton and Justin Timberlake. That performance was my introduction to Chris Stapleton… and lot of other people’s, too.

That performance vaulted the country blue singer-songwriter into the national spotlight and helped push his debut album, Traveller, to Billboard’s #1 spot and eventual double-platinum status. Not bad for three minutes’ work.

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Song of the Day #3,242: ‘When I Look at the World’ – U2

One interesting aspect of U2, one of the most popular rock acts of all time, is that they’re essentially a Christian rock band.

Most Christian rock bands explicitly market themselves as such, rather than seeking a wider audience. Presumably, they see their music as a form of proselytizing. U2 doesn’t do that. But so many of their songs are about a relationship with God that they certainly could have gone down that path.

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Song of the Day #3,241: ‘Tempted’ – Squeeze vs. Prince

David Bowie made his Round One appearance and, at least by my vote, bested his first Montauk Madness opponent. Now it’s time for another musical legend who died in 2016 to try his luck, as Prince faces off against the British New Wave band Squeeze.

This is a more difficult decision than it might seem. While I acknowledge Prince’s unique genius and his contribution to rock and R&B music, I don’t own many of his albums. But neither do I own many Squeeze albums.

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Song of the Day #3,240: ‘Leaves That Are Green’ – Simon & Garfunkel vs. Rufus Wainwright

Earlier in the first round of Montauk Madness, I voted for Paul Simon over Elton John. Now Simon shows up again, paired with Art Garfunkel, to take on Rufus Wainwright.

Simon & Garfunkel were one of my first musical loves. I owned all of their albums on vinyl more than a decade after they broke up and was delighted by every poetic turn of phrase, every gorgeous harmony.

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Song of the Day #3,239: ‘The Cowboy Mambo (Hey Lookit Me Now)’ – David Byrne vs. Taylor Swift

Today’s Montauk Madness matchup is similar to yesterday’s, in that it pits a modern-day juggernaut against an established artist likely past his prime.

Apart from Adele, nobody has the four-quadrant appeal of Taylor Swift. She parlayed country stardom into pop superstardom and is now pretty a much a genre unto herself. David Byrne is an indie rock, New Wave and world music pioneer who has influenced scores of modern musicians. Note: For the purposes of this face-off, we are considering only Byrne’s solo work, and not Talking Heads.

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