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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