I’m surprised it’s taken me so long to get to Frank Sinatra when delving into my mother’s record collection. Talking about her taste in music and leaving out Ol’ Blue Eyes is like a history of art that doesn’t mention Michelangelo. He was the untouchable King as far as my parents were concerned (“Come Fly With Me” was played at my Dad’s funeral, that song won’t sound the same ever again) and my sister and I were indoctrinated at an early age with a love of all things Frank. I probably knew all the words to “I’ve Got You Under My Skin” when I was still in nappies and just seeing the sleeve of “Songs For Swingin’ Lovers” sends me on a Proustian rush into the past.

Sinatra was something of an anachronism by the late 1960s, a hero to the older “square” generation who spent most of the decade trying to stay relevant which led to horrors like his cover of “Mrs. Robinson” (count yourself lucky if you haven’t heard that.) But one very smart move he made in 1967 was to jump on the bandwagon for all things Brazilian and Bossa and make an album with Antonio Carlos Jobim. The combo of Sinatra’s elegant phrasing with Jobim’s gentle, sun-kissed songs resulted in what I think is the coolest record ever made (in the truest sense of the word), immaculate and poised right down to it’s cufflinks. The greatest thing about Sinatra’s singing was how he never rushed a song, even uptempo ones. Try and sing along to one of his records and you’ll soon find yourself overtaking him as he hangs back, savouring every syllable of the lyrics. With Jobim he slows down to a mellow and languid crawl, his voice barely above a whisper. But I can’t describe the record any better than how the sleeve notes did:

“It had begun like the World Soft Championships. The songs, mostly by Antonio Carlos Jobim. Tender melodies. Tender like a two-day, lobster-red Rio sunburn, so tender they’d scream agony if handled rough. Slap one of his fragile songs on the back with a couple of trumpets? Like washing crystal in a cement mixer.
Seemed like the whole idea was to out-hush each other. Decibels treated like daggers. The arranger tiptoeing about, eliminating some percussion here, ticks there, ridding every song of clicks, bings, bips, all things sharp. Doing it with fervor matched by Her Majesty’s Silkworms.”

As I’ve mentioned before my mother was a big fan of all the Latin-flavoured adult pop around at the time so Sinatra making a record with Jobim was a match made in heaven for her and this got heavy play on our old mono Bush record player. Aside from lovely Jobim tunes like “How Insensitive” the album has a few Bossa-fied versions of old standards like Cole Porter’s “I Concentrate On You” which drips with the sleek ambience of a jet set lounge. When those flutes play you can almost hear the lights dimming and the clink of ice cubes dropping into heavy glasses of Jack Daniel’s.

Download: How Insensitive – Frank Sinatra & Antonio Carlos Jobim (mp3)
Download: I Concentrate On You – Frank Sinatra & Antonio Carlos Jobim (mp3)
Buy: “Francis Albert Sinatra & Antonio Carlos Jobim” (album)

Bonus feature: This clip of Sinatra singing “The Girl From Ipanema” with Jobim is just too wonderful for words. Watch and learn kids, this is what cool really looks like.