1. “One For My Baby” (click title to listen)
From Sinatra Sings For Only the Lonely (Capitol, 1959)

I can’t remember if I bought the Only the Lonely album in my junior or senior year of high school, but I’m absolutely certain it was high school, because I’d read an article in a British magazine about how it was one of the greatest breakup albums of all time.

Being a melodramatic teenager who expunged the sorrows of unrequited love in front of a stereo system, I thought, “That’d be a good album to have just in case.” You can’t really listen to that album when you’re in a happy mood—it’s unbelievably heavy and it really saps you as a listener.

There are a few cuts on it I can take if I’m in a good mood, but as a whole, it’s best left to when you’re really in the dumps and you feel that you’re heart was created not for the purpose of pumping life through your body, but instead more of a toy for women to kick around at will.

I listened to this album A LOT my freshman year at Marquette, so you can imagine how much fun I was to be around in those days.

But as heartbreaking as it is, I can listen to “One For My Baby” any time. It’s kind of become a cliched song, and were it not for Green Day writing that “Good Riddance” song, it’d probably be more of a go-to for TV series finales. All the different versions that have been recorded and performed down the years are useless, ersatz takes on this.

This is the sound of absolute emotional devastation, but it’s delivered in such a way that it can comfort you when you’re sad and even reassure you if you’re happy.

By the way, it also just happens to have the greatest piano track ever laid down on record. It’s Frank’s show, but Bill Miller deserves a hell of a lot of credit for setting the stage for Frank’s best performance.

I remember my senior year of college, my roommate went through a pretty messy breakup with his long time girlfriend, and he spent a couple weeks listening to Maroon 5’s Songs About Jane. About two weeks into his retreat into a bruised psyche, he decided to talk music with me and told me of that idiotic album. “Man, you really listen to sad songs in a different way when you’ve been through what I’ve been through. This album’s really amazing. I feel like it’s about me.”

As he was one of my best friends, and I was acutely aware of the devastation and emotional turmoil he was fighting his way through, I started cursing him out for even suggesting that Maroon 5 could help anyone in any facet of life and moved toward my CD tower to find Only the Lonely.

I was going to give it to him as a way to wise up. But then I thought that if he’s dumb enough to elevate Maroon 5 to such a therapeutic level, he didn’t deserve to listen to Only the Lonely. So I told him to man up and get the f*ck out of my room. I’ll keep this one for myself, thanks.

Rookie.

This post was authored by Paul Snyder.