Right way / Wrong way: Songs about Bob

This year I heard what has to be one of the best Bob songs ever, and it nearly washed away the memory of one of the worst songs I’ve ever heard—about Bob or anyone else.

Right way

Bob – Drive-By Truckers

Let’s start with the good Bob song, from the Drive-By Truckers’ universally awesome Brighter than Creation’s Dark.  “Bob” sounds like a like a Don Williams classic until you realize the song is subverting country music’s “Simple Man” and rambler tropes by revealing its guileless hero as not-quite-all-there loner who never married and still lives with his mom. Not because he’s gay, you understand. But because he’s a misanthrope who’s just self-aware enough to wonder whether he and sad bastards like him aren’t being incrementally eliminated by cheap cable internet connections and the liberal media. It’s a two-minute microtragedy, and it’s a REALLY GOOD SONG.

Wrong way

Losing My Way – Justin Timberlake

If you want to hear a character study that’s absolutely, hilariously awful, I urge you to check out Justin Timberlake’s “Losing My Way.” I was a huge fan of Timberlake’s Futuresex/Lovesounds, but its worst song (by many, many miles) is this cautionary tale about how drugs can tear apart your life. Here are song’s two verses:

Hi my name is Bob and I work at my job
I make forty-something dollars a day
I used to be the man in my hometown
Until I started to lose my way
It all goes back to when I dropped out at school
Having fun, I was living the life
But now I got a problem with that little white rock
See I can’t put down the pipe

Now you gotta understand I was a family man
I would have done anything for my own
But I couldn’t get a grip on my new found itch
So I ended up all alone
I remember where I was when I got my first buzz
See I thought I was living the life
And the craziest thing is I’ll probably never know
the color of my  daughter’s eyes

I think Justin Timberlake may have violated the first rule of writing, which is write what you know. Love him or hate him, JT is a ridiculously talented musician who was raised in relative wealth and trained as a performer from a very young age. If that’s not bad enough, dude is an amazingly good athlete who’s become a near-scratch golfer in his spare time. My point is this: Timberlake has not wasted one moment of his life in the kind of pointless, soul-crushing squalor faced by the average crack addict. And that’s why “Losing My Way” is a particularly good example why people who don’t do drugs should never, ever urge other people not to do drugs. Like Nancy Reagan before him, such advice is likely to have the opposite effect.

Justin probably should have left the song off the album, instead he tried to salvage it by including it on the album’s weaker half and adding a rote bridge before finishing off with a gospel choir. As I said, I really like Justin Timberlake. But this is very good evidence that I shouldn’t.