Day 23: A Song that You Listen to When You’re Sad

Sadness is such a consistently powerful fuel for musical creativity that it leads one to wonder: how successful can a musician be before (s)he starts to suck?  Take, for example, someone who once was one of the saddest, most shockingly talented songwriters in recent memory: Ryan Adams.

After a short stint with the awesomely-named Patty Duke Syndrome, Ryan set off with the band Whiskeytown.  Together, the band wrote beautifully depressing music that dripped with emotion and authenticity (and more than a few drips of whiskey, no doubt).  A classic couplet from the song I’ve put below:

Could go out tonight, but I’m not sure what for.  Call a friend or two, I don’t know many more.

Sit & Listen To The Rain, Whiskeytown

With their initial records, Whiskeytown enjoyed some success.  But, thankfully, not nearly enough to overcome their profound sad bastard-ness.  Ryan set off on his own and made the must-own album entitled (appropriately enough) “Heartbreaker.”  Paired with Emmylou Harris on backing vocals, here’s one of the best tracks on the record: “Oh My Sweet Carolina.”  This track plays out one of Adams’ most powerful skills: the ability to tell a pretty powerfully-moving story in few mere minutes; a story told in a way that you feel there.  You may have only been below the Mason-Dixon to visit Disney, but this song will take you to San Antonio.