For some reason, at the very least when set amongst the album in my top 20, this album feels the most out of place. It is definitely the most emo album to make the list for sure and, in addition, it’s pretty straight forward country/Americana. Nope, no experimentation here. But there is just something about the emotional heft inhabiting the songs on Heartbreaker that accomplish exactly what the title suggests. The saddest album I’ve probably ever heard and an unfortunate fuel to my adolescent high school depressions. Now that I think of it, I probably wouldn't have been depressed at all if it wasn't for this album. Still, the album is perfect from front to back and one of the most beautiful records that I have ever heard.