I was pleasantly surprised by this album. As the oldest album on the list, it holds up incredibly well. The writing, instrumentals and vocals are all borderline perfect. It’s also a very sad and melancholy record, being mostly inspired by a particularly nasty breakup with his wife Ava Gardner.

The music itself is without a doubt my favorite part of this album. The strings, horns, and and occasional bells all work together to create a truly sublime score that sounds straight out of the most well-orchestrated classic Disney film you can imagine. Listening to this album is like having silk, milk and honey injected directly into your eardrums. …Actually, that sounds horrifying. Never mind, bad example.

This was a difficult and emotional album for Sinatra to make, and it shows. The lyrics are sad, the vocals are soulful and the album as a whole just gives off an incredible sorrowful vibe. Most of the songs are about loneliness, isolation and often unrequited love, which makes sense, as the album was mainly inspired by his recent separation with his wife, Ava. The emotions in this album are real and strong, and it’s easy to tell.

So overall, this was a very good album. The combination of absolutely incredible instrumentation, lyrics and vocal performances make this a truly unforgettable album A true masterpiece that you should absolutely listen to.

Next Up: Tragic Songs of Life by the Louvin Brothers (1956)