Frank Sinatra. Nat King Cole. Bing Crosby. Dean Martin.
If you have absolutely no clue who these people are, I may shed a tear. These four men are some of the most famous crooners, a kind of singing that soared to popularity in the late 50’s and early 60’s. In the sixties, these men came to popularity across all media. They sang well, dressed well, they were handsome and charming (if not fiendishly so). Many of them were known not only for their singing, but for their acting, live performances and general showmanship. In fact, the Damon-Pitt-Clooney hit, Ocean’s 11, is a remake of the 1960 film of the same name that stars both Frank Sinatra and Dean Martin.
I was born in 1999, years and years and years after these gentlemen (although calling Sinatra a gentleman may be a bit of a misnomer) were in their prime. This music is decidedly not from my era. I ought to listen to Kanye or AJR or Taylor Swift. It’s not that I don’t connect with contemporary music, but the old songs that these suave crooners deliver with such ease just connect with me. Sometimes I feel like I belong in their time, in a world of fedoras, pinstripe suits and guys and dolls.
That longing, the connection I have with this old music isn’t something that was always appreciated. I was singing Fly me to the Moon in front of my hallway mirror when I was eight, but as I got older it felt like a part of myself that I should question. If I played Unforgettable on a speaker in high school, the aux cable would very quickly be confiscated by another teenager deeming my taste in music to be strange.
It feels like an overplayed trope that I didn’t quite fit in in high school but when I went to university I finally found my people. My university friends still don’t like my old school playlists. But I do. I blast Strangers in the Night in my car as I drive my old Mazda from Stellenbosch to Cape Town because I love the way it makes me feel. People must think I’m mad. To me, though, I’m driving my 1960’s Cadillac North to New York City to see Sinatra live in concert. Care to join me?