My Way, by Frank Sinatra
I can't listen to the song My Way by Frank Sinatra with a straight face unless I've had a few drinks. It's one of those songs you really shouldn't listen to without a martini in hand. When I hear the song on the radio in the afternoon instead of over a bar karaoke machine manned by a guy propped with a bar stool, I can't help but look around with a nervous smile. It's kind of like watching reruns of Saved by the Bell or Fresh Prince--I'm embarrassed for the people around me. And it's not just the outrageous content of the song. Even after a couple light brown whiskey and Cokes, I still cringe when Sinatra rhymes "my way" with "shy way." I think the only guy besides Frank Sinatra who could seriously sing My Way is William Shatner, but only because he's insane.