Hear that lonesome whippoorwill,
He sounds too blue to fly.
The midnight train is whining low,
I’m so lonesome I could cry.
I’ve never seen a night so long,
When time goes crawling by.
The moon just went behind the clouds,
To hide its face and cry.
Did you ever see a robin weep,
When leaves began to die?
That means he’s lost the will to live,
I’m so lonesome I could cry
The silence of a falling star
Lights up a purple sky.
And as I wonder where you are,
I’m so lonesome I could cry. 
Hank Williams wrote this in his mid-20’s. He died at 29 of a heartattack, after years of alcohol- and drug-abuse.
What did he catch in this song about deep sadness?
He depicted a deeply accurate insight: real depression completely colors our experience of living. At those times, everything else we perceive — every sight, sound, odor, etc. — only intensifies the sadness. Even our experience of trees, birds and nature, conjures up only the saddest of thoughts and associations.
If we tell a depressed person, “Get up and do something,” we may be asking them to experience sadness intensified from what they’re already feeling.
As rabbis, we’re often called upon to understand the feelings of our congregants, or of other people we’re counseling. Sometimes — as with deep depression — it might not be something we’ve experienced ourselves. G-d willing, you won’t ever feel it.
But more useful and important than “understanding” those feelings in a detached, intellectual way, is for us to understand — empathetically — what it feels like to feel those feelings.
Song lyrics — especially, but not only popular songs (“Pop” here including Country & Western or any other type) — can give us a glimpse into those experiences. Beyond style and wit, the best songs have a truth to tell us about those times in a person’s life. The truest ones are the ones that last, too.
The best performances of those songs capture the truths of those moments (they’re usually longer than “moments”), too. A performer strives to invoke a feeling that’s so true, so real, that we forget it’s a “performance,” and participate in the feeling itself — even if that same performer also wrote the song.
Even if we’re not rabbis or professional counselors, there’s always a need to put ourselves in the place of those we live and work with. Empathy is a skill that begins with asking ourselves, “How would I feel in his/her place? How would I feel if it were happening to me?”
It’s easy to talk about treating all people with dignity and respect; far harder to carry through with it in all our dealings with others. We need to. Especially in Jewish organizational life.
So, let’s “enjoy” the songs, but let’s take them seriously, too.
They can help us to better empathize with those who need us.
 words and music by Hank Williams