Frank Sinatra. The Greatest Singer. Ever.

Sinatra. The Greatest Singer. Ever.

Francis Albert Sinatra. The Chairman of the Board. Ol’ Blue Eyes. Frank.


King of Cool

King of Cool

Whatever you call him, Sinatra was arguably the greatest pop vocalist to ever put their voice to tape.
His breath control, vibrato, phrasing and coloring are elements of a high standard that others should strive to attain to be a true “singer’s singer”

Growing up with the late ‘70s and early ‘80s edition of Sinatra, I was exposed to the caricature of the “Ring-a-Ding-Ding,” whiskey-toting, cigarette puffing crooner. Joe Piscopo’s impression of Sinatra on Saturday Night Live didn’t help matters as far as wanting to explore more of his music – he seemed like a doofy senior citizen to me. “My Way”, “New York, New York”, “Come Fly With Me” and “Send In The Clowns” were all I really knew before I started my first college semester studying broadcasting. We got to choose some of our own records (yes, we played real vinyl records on the radio back then) and one of the guys in my class brought in “Only The Lonely” and loved to play “One For My Baby” and at that point, I was hooked. I tracked through that album a couple times in those first few weeks of school.


“Frank Sinatra Sings for Only the Lonely” – 1958

”Buy Only The Lonely”

At that time, I was a much bigger Nat ‘King’ Cole fan than a Frank fan – but Nat never quite had that angst or revelation of raw emotion that Sinatra had. Sinatra all but created the “concept” album by having songs tied together in a specific theme beginning with his earliest work with Capitol in the early 1950’s.
Frank had an independence to him an “edge” of sorts. And at 20 – I thought that “edge” mixed with the Vegas classiness was about the coolest thing since Jack Kerouac.

I was lucky enough to see Frank Sinatra perform live at the Met Center in Minneapolis in January of 1992. There was a crazy blizzard that night and I had purchased tickets for my mom as a Christmas gift and I’ll be damned if we were gonna miss that show due to some snow. Traffic was at a stand-still but we got into the arena just in the nick of time as we saw the house lights go down as we neared the doorway to our seating section. We had seats about 20 rows from the stage and I could see the monitors with the lyrics in case the 75 year old singer had a memory lapse. Needless to say, the performance was phenomenal and he sounded really strong but age was setting in for sure. I even got a Sinatra tour shirt as a memento from that show – sadly the XL was cut to a slim Large and I’ve never even attempted to put it on. Hopefully, someday that will happen.

My buddy and writer/author David Haight and I were HUGE Sinatra fans coming out of college in our early ’20s and he became even more obsessed with Sinatra’s catalog and history than I ever thought of being and when I need to know more about a Sinatra song or album, I turn to him for the answer or recommendation of what to explore next. I’m like a cat with a shiny object and get distracted by other music and rarely dig as deep as he does on a band or artist he connects with on a passionate level.

We were really into Frank’s melancholy albums he recorded for Capitol Records –“Frank Sinatra Sings for Only The Lonely”, “Where Are You?”, ”No One Cares” and “In The Wee Small Hours.”

Where Are You

“Where Are You?” 1957

”Buy Where Are You?”

In The Wee Small Hours - 1955

“In The Wee Small Hours” – 1955

”Buy In The Wee Small Hours”

My favorite of all of them was “In The Wee Small Hours” – I just loved his versions of jazz-pop standards “Mood Indigo” and “What Is This Thing Called Love” and the beautiful “When Your Lover Has Gone” (of which Sinatra reportedly broke down crying after the master take overcome with emotion) and the title track “In The Wee Small Hours”

I love this album so much that I have a tattoo of the album cover on my left arm.

That's "Sweat Equity," kids.

That’s “Sweat Equity,” kids.

One summer, David and I were entertaining a couple ladies that we met through my record store and we partied up at his Dad’s cabin on Lake Ida, just north of Alexandria, MN. We each favored a different girl and it seemed it was likewise with them and while David and his girl went for a walk down the dirt roads around the point, I got to spend that time attempting to seduce a girl I had a crush on for a few months, who I found out had also went on a date with one of my co-workers.   The booze had been flowing like a faucet most of the day with both girls passing out and napping in the early afternoon and “Hallie” was getting all worked up that Martin (my co-worker) wasn’t answering her calls (and she was calling him almost immediately after the other two left the cabin) – at that point I knew she was into him and not me, so I decided to get absolutely shit-hammered, which was an acceptable response at that time and in hindsight seems really sad and emo-boy.
I put on the Afghan Whigs’ notoriously sexist “Gentlemen” album for a few tracks to get that rage out then sadness overtook me and my sensitive ass put Sinatra’s “No One Cares” album on the stereo and when David and “Kara” came back from their walk, I had managed to line up about 7 beers and a pissy attitude. As the song “I Don’t Stand a Ghost of a Chance” came on – I loudly stated – “D’ja hear the song, Dave? You know what this song is called?” “It’s called I don’t stand a ghost of a chance with you. Pretty goddamn fitting” – we still get a good laugh out of that moment after all these years.

No One Cares

“No One Cares” – 1959

”Buy No One Cares”

On May 14th, 1998 I received a phone call at the record store and David was on the other end of the line crying and maybe a little intoxicated and said “He’s gone. Frank died.” My heart sank. I didn’t get weepy but I just felt like a huge light went out that day – and it did. About an hour later I got a call from the store owner saying someone from cable access would be coming to interview me at the store about Sinatra’s passing, legacy and my silly tattoo.

My favorite Sinatra song was one I really only “got” about 8 years ago while I was going through one of the worst periods of my adult life. It was a cool, rainy summer evening and I hadn’t been working in months and couldn’t land a job and I felt like ten kinds of sack-whooped ass damn near every day.

I immediately connected with the opening string parts – it felt so happy and “Spring-like” and then Frank took over and just laid it down to street level. His baritone sweeping from the edges of bass to tenor, the phrasing, vibrato and, ultimately, that biting emotion only he could project. There were no other pop standards singers that could ever touch him.

That song is a jazz standard called “When the World Was Young” otherwise known as “(Ah the Apple Tree) When the World Was Young” – with English lyrics written by the great Johnny Mercer on the French song “Le Chevalier de Paris” written by M. Philippe Girard.  It’s off Frank’s final contract album for Capitol, reuniting him with his old Columbia Records orchestral arranger, Axel Stordahl.

"Point Of No Return" - 1962

“Point Of No Return” – 1962

”Buy Point Of No Return”

There are a handful of solid takes on this song but only Frank’s brings you closest to the teller of the story and makes you feel his words.

The harps melting into the other strings, bird-like flute runs, the low bass lending a shadow of sadness.

The recordings are so well-engineered that you can close your eyes and it’s damn near like having the Chairman in the room right next to you. The best kind of ghost if you ask me.

So here it is. Enjoy.
Explore the albums I mentioned and dig deeper than a greatest hits compilation.
You’ll thank me later.



Jason is a freelance photographer, writer and admitted Frank-O-Phile.