Song of the Day #3,220: ‘Prove My Love’ – Lucinda Williams vs. Garbage

Closing out this first week of Montauk Madness, we have the fifth matchup from Round One, pitting Lucinda Williams against Garbage. Folk rock vs. industrial rock. Organic vs. electronic.

As much as I like Garbage, particularly their first three albums, this is another easy pick. Ideally, the first round should be easy, though peeking ahead I see a couple of hair-pullers on the horizon.

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Song of the Day #3,219: ‘New Young’ – Josh Rouse vs. Peter Gabriel

I haven’t had a difficult choice to make through the first few matchups in Round One of Montauk Madness, and that won’t change today.

Peter Gabriel faces off against Josh Rouse. An art rock pioneer against a prolific but low-profile indie singer-songwriter. While I love Gabriel’s So — a bona fide classic — and enjoy tracks from his other solo records, he hasn’t consistently impressed me the way Rouse has.

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Song of the Day #3,218: ‘These Dreams of You’ – Van Morrison vs. Barenaked Ladies

The random nature of the matchups in Montauk Madness serves up some interesting pairings. This is probably the first time Barenaked Ladies and Van Morrison have been mentioned in the same breath.

Initially, I went with Barenaked Ladies here, my rationale being that I own and enjoy nine of their albums vs. only one by Morrison.

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Song of the Day #3,217: ‘I Know Him Too’ – Tift Merritt vs. Frank Sinatra

Our next match-up in Round One of Montauk Madness pits the legendary Frank Sinatra against the tragically under-appreciated singer-songwriter Tift Merritt. A no-brainer, right? I agree… Tift Merritt advances.

Sinatra acolytes (like my parents) will scoff at this choice, I’m sure. But as much as I love Sinatra’s voice, and his interpretation of classic songs on such albums as Only the Lonely, Songs For Swingin’ Lovers, In the Wee Small Hours and Watertown, I find it hard to vote for a non-songwriter over an excellent and prolific one.

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Song of the Day #3,216: ‘She’s Always a Woman’ – Billy Joel vs. Michael Penn

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].

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Song of the Day #3,215: ‘Gangway’ – Guster

Here’s a nice song from Guster’s 2015 album Evermotion. Guster is a band that just doesn’t seem to record bad music, even if I don’t fall in love with everything they do.

When this track popped up as today’s Random iTunes Selection, I didn’t know it. I haven’t listened to Evermotion much and this is a deeper cut. But I knew it would be a perfectly enjoyable song, with pleasant vocals and an easy groove. Because that describes every Guster song.

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Song of the Day #3,214: ‘Vultures’ – John Mayer

John Mayer has a knack for making me like genres I don’t usually dig.

Take ‘Vultures,’ a song from Mayer’s excellent 2006 album (Continuum), which sounds like a lost Steely Dan track.

I hate Steely Dan. OK, that’s a bit strong, but I definitely don’t like them. And yet I love ‘Vultures,’ and the rest of Continuum, which has the same general vibe.

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