Fedora? No (My) Way

Frank Sinatra always seemed old to me.

When I was growing up, the Rat Pack already seemed impossibly old and out of touch. And my friends and I puzzled over why people would ever pay attention to them.

Growing up, there was only one kid in school who listened to Frank Sinatra (and he would regularly wear a fedora, suspenders, and powder-blue boat shoes instead of scuffed-up jeans and sneakers). The school bullies thought his retro act was so weird that they left him alone (perhaps for fear of catching the virus that caused worship of Nelson Riddle).

So while most of our contemporaries needed a backbeat and electric guitars, my fedora-wearing friend was content with a big band and old Sinatra albums. And only the old albums. If you made the mistake of mentioning "My Way," he'd scoff and dismiss it as crap.

It was a feeling Sinatra shared. And yet that song fueled his live act for nearly 30 years (and stoked demand for that live-act in the post-Beatles era).

Sure, Sinatra was too much of a showman and too musical to ever completely destroy a song. But still I can't help wondering if Sinatra, when he was doing this...


...would have been happier doing something more like this:


And more importantly, what would Sid Vicious have looked like in a fedora, suspenders, and powder-blue boat shoes?