For me, the music of Frank Sinatra is indispensable. Almost twenty years ago, I stopped listening to (new) rock music and started investigating the musical past. It happened because rock was too noisy. I was at a point in my career where I did not want to come home after a long day to loud banging noises and singers with “interesting” voices. I was drawn instead to the class, sass, and extraordinary talent of Ol’ Blue Eyes.

Frank’s music was kept in the section of the music store devoted to “Easy Listening.” To me that meant uncool elevator music and middle-agedness. Little did I know how utterly cool Frank was, is, and always will be. I embraced middle age well before I hit forty. My taste in music changed. I wanted nuance, style, and vocal artistry. I wanted cocktails and jazz and the Great American Songbook.

I didn’t know that much about Sinatra at the time, but I liked his voice. At first I couldn’t tell him from other singers of the period, but I quickly came to recognize and prize his distinctive sound. He changed over the years, of course, morphing from gentle, velvet-toned crooner to confident swinger to whiskey-soaked Chairman of the Board. These days, listening to Frank is like relaxing in a favorite comfy chair, or (if in swinging mode) like dancing with a longtime love.

Here are my Desert Island Sinatra tracks, in chronological order:

I’ve Got A Crush On You. One of the first Sinatra items I bought was a boxed set from the Columbia years, the period when he was still wearing the floppy bow ties his wife sewed for him. My favorite song from that very rich collection is this George and Ira Gershwin classic. It reveals the lush romanticism of The Voice, the erotic quality that turned Sinatra into an idol for the “bobby soxers” of the Forties. Well before the Beatles, he caused screaming fits, fainting and riots among a legion of fans. The song also includes a killer trumpet solo by Bobby Hackett. You’ll recognize his sound from Woody Allen movies.

I’ve got a crush on you, sweetie pie
All the day and night time, hear me sigh
I never had the least notion
That I could fall with so much emotion

The world will pardon my mush
‘Cos I have got a crush, my baby, on you

Pennies From Heaven. Sinatra’s übercool Period commenced when he signed with Capitol Records in 1953. Nelson Riddle’s sophisticated arrangements perfectly complemented Sinatra’s swinging new persona. This was a high point in Frank’s career. At the time, he had just won an Oscar for From Here To Eternity, and he had begun his storied 43-year love affair with Vegas, first at the Desert Inn, and then at the Sands.

A favorite album of mine is Songs For Swingin’ Lovers (1956), which includes “Pennies,” by Arthur Johnston and Johnny Burke. The song was introduced by Bing Crosby in the film of the same name, and immediately became a classic. Frank’s version is more upbeat and less wistful than Bing’s, but its whimsy and charm are undiminished.

Every time it rains, it rains
Pennies from heaven
Don’t you know each cloud contains
Pennies from heaven?
You’ll find your fortune falling all over the town
Make sure that your umbrella is upside down

Ring-A-Ding-Ding was Sinatra’s first album with Reprise (1961), and the title song by Sammy Cahn and Jimmy Van Heusen is a keeper. At first it strikes you as a novelty song, but once its internal rhymes have time to sink in, you’re hooked.

How could that funny face that seemed to be commonplace
Project you right into space? Without any warning
Don’t know if it’s morning, night-time, winter or spring
What’s the difference: Ring-a-ding ding, ring-a-ding ding, ring-a-ding ding

No Desert Island list would be complete without “Fly Me To The Moon,” which manages to be sad and joyful at the same time. It celebrates the mystery and wonder of falling in love, yet the melody itself hints that all joys are ephemeral. The song was composed by Bart Howard in 1954, and originally named “In Other Words.” It was oft-recorded before Sinatra’s 1964 uptempo version with Count Basie, but in my opinion, he OWNS this song.

Fly me to the moon
Let me play among the stars
Let me see what spring is like
On Jupiter and Mars
In other words, hold my hand
In other words, baby, kiss me
Fill my heart with song
And let me sing forever more
You are all I long for
All I worship and adore
In other words, please be true
In other words, I love you

“Luck Be A Lady” is from the immortal musical Guys and Dolls by Frank Loesser. I’ve always loved it for the clever, slightly naughty lyrics, in which gambler Skye Masterson admonishes Lady Luck to mind her manners. The song was introduced on Broadway by Robert Alda, father of Alan, and the cast album is fantastic. Marlon Brando played Skye Masterson in the movie, while Sinatra himself played Nathan Detroit. Thank goodness he also recorded this stunning, knock-it-out-of-the-park version of the song (from the live album Sinatra at the Sands, 1966).

Luck, let a gentleman see
Just how nice a dame you can be
I know the way you’ve treated other guys you’ve been with
Luck, be a lady with me
A lady never leaves her escort
It isn’t fair, it isn’t nice
A lady doesn’t wander all over the room
And blow on some other guy’s dice

“New York, New York” is the tune I love best from his late, baroque period. It showed that Sinatra still had the mojo at the age of 64. It was recorded in 1979, after Liza Minnelli introduced the song in the film New York, New York, directed by Martin Scorsese. You cannot hear this song with indifference. It floods you with all the energy of the City That Never Sleeps.

These little town blues
Are melting away
I’ll make a brand new start of it
In old New York
If I can make it there
I’ll make it anywhere
It’s up to you
New York, New York

2015 is the centenary of Frank Sinatra, who was born in 1915 and died on May 14, 1998. Unequaled as in interpreter of American popular song, he has left us a treasure trove of recordings, enough to study and savor for a lifetime. Which is exactly what I plan to do. Thanks for all of it, Beautiful Man!