Song of the Day #3,956: ‘Strangers in the Night’ – Frank Sinatra

‘Strangers in the Night,’ recorded by Frank Sinatra in 1966 for an album of the same name, reached #1 in both the U.S. and the UK. It won three Grammy awards, including Record of the Year and Best Male Pop Vocal Performance. The album became the most commercially successful in Sinatra’s career.

And yet Ol’ Blue Eyes hated the song. When he was first given the sheet music, he reportedly told his aid “I don’t want to sing this, it’s a piece of shit.”

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Song of the Day #3,662: ‘Sinatra 75: The Best is Yet to Come’ – Frank SInatra

Today is my father’s 75th birthday, a grand milestone for a grand man!

I’m cheating a bit by not featuring an individual song but instead an entire TV special as today’s SOTD. This is the 1990 celebration Sinatra 75: The Best is Yet to Come, a TV special that combined documentary footage with a live performance by the birthday boy himself.

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Song of the Day #3,649: ‘I’ve Got You Under My Skin’ – Frank Sinatra

How about a little Cole Porter to close out your weekend? And not just Cole Porter, but Cole Porter performed by Ol’ Blue Eyes, the Chairman of the Board, the one and only Frank Sinatra.

This version of ‘I’ve Got You Under My Skin,’ the most famous, was orchestrated by Nelson Riddle and is notable for the rousing instrumental crescendo and trombone solo that kick off the song’s second minute.

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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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