Song of the Day #3,367: ‘One for My Baby (and One More for the Road)’ – Frank Sinatra

After trotting out the songs that make us happy yesterday, you might have predicted that today’s installment of the 30 Day Music Challenge would call for ‘A Song That Makes You Sad.’

As a self-professed lover of melancholy music, I have no shortage of songs to choose from today. Many of my favorite artists (think Aimee Mann and Belle & Sebastian) are known for writing sad songs. But I decided to reach back to a classic from well before my time.

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Song of the Day #3,265: ‘She’s Got a Way’ – Billy Joel vs. Frank Sinatra

OK, now it gets interesting! Welcome to Round Two of Montauk Madness. The 32 artists who survived Round One now advance to face each other in a battle to reach the Sweet Sixteen.

Both Billy Joel and Frank Sinatra cleared Round One without breaking a sweat. Joel received 95% of the vote in a matchup against Michael Penn, while Sinatra picked up 86% against my beloved Tift Merritt.

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Song of the Day #2,938: ‘I Get a Kick Out of You’ – Frank Sinatra

sinatraLast week I defended Bob Dylan’s foray into the music of Frank Sinatra, but today’s random iTunes selection serves as a nice reminder that nobody sings a Sinatra song like Sinatra.

‘I Get a Kick Out of You’ is a Cole Porter tune originally written for the Broadway music Anything Goes. That was in the mid 1930s. Sinatra recorded two studio versions of the song, one in 1953 and one in 1962 (the latter is the version below). Funny that this song was already an oldie when Frank sang it for the first time.

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Song of the Day #2,817: ‘Lady Day’ – Frank Sinatra

watertown_sinatraMy second favorite album of 1970 is Frank Sinatra’s little-known but no less classic concept album Watertown.

The album tells the tale of a man picking up the pieces after being left by his wife. He raises his two children, earns the sympathy of his neighbors, and quietly tries to win her back. The record ends with him waiting in the rain at a train station, the wife having gone back on her promise to return.

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Song of the Day #2,706: ‘Have Yourself a Merry Little Christmas’ – Frank Sinatra


I’m taking a little Christmas break this week while I prepare the countdown of my favorite 2015 songs.

To get everybody in the holiday spirit, I’ll post five renditions of my favorite Christmas song, ‘Have Yourself a Merry Little Christmas,’ starting with Old Blue Eyes.

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Song of the Day #2,487: ‘You’re Getting To Be a Habit’ – Frank Sinatra

sinatra_swingin_loversI’ve written quite a bit about my love of the melancholy Frank Sinatra — Only the Lonely, In the Wee Small Hours and all that good stuff.

But it’s hard to deny the appeal of Sinatra’s flip side, the uptempo, jazzy style epitomized on 1956’s Songs For Swingin’ Lovers. This album was the unlikely successor to In the Wee Small Hours of the Morning, making for one of the best one-two punches in music history.

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Song of the Day #2,431: ‘In the Wee Small Hours of the Morning’ – Frank Sinatra

wee_small_hoursWell here’s a lovely treat on a Random iTunes Weekend — the title track from Frank Sinatra’s sad-sack concept album, In the Wee Small Hours of the Morning.

I love the swinging Frank Sinatra of ‘Fly Me to the Moon’ and ‘Come Fly With Me’ but my true affection for Ol’ Blue Eyes lies with the depressing records.

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