Remembering Frank Sinatra at 100, and why "New York, New York" doesn't make my Sinatra Top 5

So today is the 100th birthday of Francis Albert Sinatra, my favorite singer of all time. He was a great vocalist, and a pretty good actor, too (check out The Manchurian Candidate to see one example of what I'm talking about.)  Part of me wishes I were alive in the era of Sinatra's prime. You know, back when they called women "dames." Heck, I would have made a great sassy dame back in the day! (Squawker Jon just chimed in to say that I am a sassy dame right now! He wouldn't say "great," though. Heh.)

Anyhow, what I like about Sinatra, besides his voice, is that he hit rock bottom, and then had arguably the greatest comeback in show business history. Such an epic comeback, only a horse's head in a bed would seem to explain it. Although that Godfather story didn't really happen, we don't know how much Sinatra's, um, connections, played in him getting the Oscar-winning role as Maggio in From Here to Eternity. Heck of the movie, by the way – watching it will put what you thought your parents' or grandparents' generation was about in a whole new light! (For one thing, Donna Reed, George Bailey's wife Mary in It's a Wonderful Life, is a prostitute in this film. But I digress.)

Anyhow, Sinatra didn't live a golden life. He had emotional scars. He had lots of downs, and romantic misery, and the like. He spent sleepless nights longing over lost loves, most notably Ava Gardner. All of this gave an edge to his singing, and is much of the reason his legend endures.

The way Sinatra didn't just sing but live his songs is part of the reason I still listen to him so often. I dig Sinatra's musing amid misery. Sorry, but I just can't relate to people who have lived perfect, easy lives. Give me the Sinatras or A-Rods of the world over the Jeters of the world any day. I want to read and learn about the people who've made mistakes, and lived to tell the tale. Speaking of which, I just started reading Ben Bradlee Jr.'s biography of Ted Williams, a very flawed (well, he was a Boston Red Sox!) but interesting individual. Good book so far!

I also have to admit finding it amusing to read recently about how Sinatra detested "My Way," finding its egomaniacal lyrics way too much. As the Wall Street Journal explained his thinking, "It would have seemed like the tackiest thing imaginable to stand in the middle of Madison Square Garden and shout out to the world how great he was." Somebody ought to have reminded team player Jeter about that, when he had that infamous Nike "My Way" commercial as part of his endless retirement tour!

Anyhow, I am such a Sinatra fan, I even liked one of the songs Frank's kids did. His daughter Nancy's "These Boots Are Made for Walking" is my top go-to karaoke song, because her lack of vocal range matches mine. Plus she's good friends with Morrissey, one of my heroes.

So, in honor of Frank Sinatra's b-day, I'm going to list my five favorite Sinatra songs, in reverse order, from 5 to 1. And no, "New York, New York" does not make this current list. It's a little overplayed at this point for me! Sorry.

5. "The Lady Is a Tramp": I still don't know what the heck the lyrics in this song mean. Why is the lady a tramp because she doesn't show up late to the theater, and because she won't dish the dirt with the rest of the girls? Even if it's meant facetiously, it still doesn't make much sense to me. Nonetheless, I still love this song!

4. "It Had to Be You": One of my favorite movies of all time is When Harry Met Sally. And Sinatra's version of this song highlights the most pivotal scene in the film. One of the movie scenes where I can recite every word of dialogue, for whatever that's worth! Harry Connick, Jr. also sings the song in the film, which is an okay song. But Sinatra's version kills.

3. "Luck Be a Lady Tonight": Longtime Subway Squawkers readers may know that Guys and Dolls is one of my favorite musicals ever. I know all the songs by heart. I am also a big believer in "yeah, chemistry," as Marlon Brando's Sky Masterson puts it in the film. But as sexy as Brando was in that role, he couldn't sing a lick. Sinatra, who plays Nathan Detroit in the film, was peeved he didn't get the part, which has the best songs, with "Luck Be a Lady Tonight." Looking back on it, Sinatra sang the heck out that song on his own, years later. But Brando sold it with his looks and charisma. Click the links and see for yourself.

2. "The Way You Look Tonight": Some of the best lyrics of any Sinatra song. Phrases like "keep that breathless charm" and "that laugh that wrinkles your nose, it touches my foolish heart" are so memorable. What woman wouldn't want a man to sing this song about her? A classic. Even the instrumental part of this song is terrific.

1. "I've Got You Under My Skin":  Many people consider this Sinatra's greatest song. So do I. The great Nelson Riddle worked with Sinatra on the arrangement of this song, but the instrumental crescendo in the middle of "I've Got You Under My Skin" was Sinatra's idea.  Someday, I will dance with someone to that part of the song; it's just so perfect! I also loved this Vanity Fair description of Sinatra regarding this song, which talks about his "terrible impatience—with the incompetence and stupidity that were so rife in the world, with things he needed to happen instantaneously, and so rarely did. The realization that he was like nobody else, and therefore destined to be alone. His terrors: of aloneness itself; of sleep, the cousin to death. And always, always, the vast and ravening appetites." That sums up Sinatra in a nutshell.

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Honorable mention: "That's Life," "Fly Me to the Moon," "Summer Wind," "I'll Be Seeing You," "All or Nothing at All," and "It Was a Very Good Year." In closing, check out Sinatra, with Count Basie, performing "Fly Me to the Moon" to some prisoners. Good stuff!


Do you have a favorite Frank Sinatra song? Tell us about it!