A wonderful 1980s Book-of-the-Month Club music collection, Songs of New York

In my not-so-humble opinion, what separates a truly iconic city from many other fine places is that the great 20th century lyricists and composers wrote songs and music about them. They are the stuff of the Great American Songbook (and that of London and Paris, too).

Here are some of my favorite songs about New York, San Francisco, Chicago, London, and Paris. Sinatra versions predominate; he knew how to croon tunes about great cities.

Click, listen, watch, and enjoy.

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When I decided to go to law school at NYU in New York City in 1982, I did so sight unseen. I didn’t have much money, so I evaluated law schools by studying their catalogs and consulting write-ups about them in published guidebooks. (This was pre-Internet, of course!) I finally saved up enough cash to visit New York for the first time, during the summer before starting law school. I came back knowing that I had made the right decision. Sinatra’s “New York, New York” quickly became my personal anthem, and it still gives me goosebumps to listen to it.

“Take Me Back to Manhattan” is a Cole Porter number often included in productions of Anything Goes. This version was performed by Judy Kaye for a 1980s collection, Songs of New York (pictured above).

True, “Rhapsody in Blue” is a musical composition, not a song. But as this video set to George Gershwin’s masterpiece will attest, it is a perfect ode to New York City. I can listen to it over and again.

The “Lullaby of Broadway” was written in 1935 and is now part of stage versions of 42nd Street. This is a great video of the 1980s Broadway production, starring Jerry Orbach (later of Law & Order) in the lead role, which I saw in 1984.

When I opted for law school in New York, it marked one of my early forks in the road. Before deciding to go east, I had looked very, very hard at schools in California and, especially, in the Bay Area. On occasion, but without regrets, I’ll wonder what if. “I Left My Heart in San Francisco” by Tony Bennett gets me nostalgic for a city I’ve only visited.

I grew up in northwest Indiana, right across the state border near Chicago. I took Chicago for granted back then, but today I appreciate it as a big, brawny, quintessential American city. “Chicago (That Toddlin’ Town)” is my favorite song about the Windy City, and no one does it better than Sinatra.

“My Kind of Town” is Sinatra’s other tribute to Chicago, and it’s a great song too.

“A Foggy Day (in London Town)” is part of the George and Ira Gershwin songbook, and it sounds especially fine with Ella Fitzgerald and Louis Armstrong doing the honors.

“A Nightingale Sang in Berkeley Square” is a wonderfully evocative song about London during the Second World War era, here performed by the incomparable Vera Lynn. It’s one of my favorites, one that I sing often in my weekly voice class and at open mic nights.

“I Love Paris” is another Cole Porter standard from the early 50s, just years after the end of the war. Sinatra captures the city’s beauty in this rendition.

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What? No song about Boston, the city in which I’ve lived for over 20 years? Sadly, no. Boston has its attractions, but there’s no classic standard to mark it. I’ll have more to say about that in a future post.