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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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Song of the Day #3,213: ‘Memphis, Tennessee’ – Chuck Berry

My final Chuck Berry song of the week was released in 1963 and has a different feel than the rockers I’ve featured so far.

‘Memphis, Tennessee’ is a nice showcase for Chuck Berry the storyteller. It’s about a man trying to track down a lost love, Marie, who turns out to be his daughter, taken away by her momma.

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