Post-Millennial Classic: “Outfit” by Drive-By Truckers, One of the First Examples of Jason Isbell’s Songwriting Brilliance

Before he was known as one of the most acclaimed singer/songwriters of the modern era, Jason Isbell plied his trade as a guitarist with Drive-By Truckers. He wasn’t with that standout band long before the full range of his talents started to shine through on stunning songs like “Outfit.”

The song tackles a father-son relationship with honesty and insight rarely achieved in a four-minute song. And “Outfit” was one of the first indications that Isbell was bound to become a star in his own right, instead of just a supporting player.

Isbell’s Spotlight Turn

Coming off their highly acclaimed 2000 concept album Southern Rock Opera, Drive-By Truckers needed an extra guitarist for the tour to support the record. Enter Jason Isbell, an Alabama native who had been a fan of the band and had known some of the principals for years, including lead singer and songwriter Patterson Hood.

When Isbell came aboard, he was just 22 years old, but he had already been writing songs for quite some time. He joined the Truckers in the studio for their follow-up album to Southern Rock Opera, and he submitted a few songs for the band’s approval. Hood liked one (“Decoration Day”) so much that he made it the title track, and built another concept up around it.

But Isbell wasn’t done there. He also turned in “Outfit,” which allowed him to look back at his relationship with his father. The two are separated by only 19 years in age, but that didn’t stop his father from giving some worldly advice, as Isbell explained in an interview with Men’s Health:

“When I went on the road, he was very concerned. I had lived a little bit of a sheltered life in a very small town—not even a town, we lived in the country. And I think he was a little concerned about some of the things I’d be exposed to.”

Folks who knew little about Isbell were floored when they heard the accomplished songwriting he brought to the table for this already established band. He would continue to do so for the next two Truckers albums before stepping out on his own. His impeccable track record since then proves the level of writing he reached on “Outfit” was far from a fluke.

What is the Meaning of “Outfit”?

In Shakespeare’s Hamlet, Polonius gives a speech to his son Laertes upon his imminent departure from home. (That whole Neither a borrower nor a lender be and To thine ownself be true shtick, remember?) Consider “Outfit” in a a similar light, albeit with the setting moved from Denmark to Alabama, and the stakes changed from palace intrigue to rock-star excess.

He starts by wishing his son something better than what he has for himself, warning him what not to do to avoid a similar fate: Keep dropping the hammer and grinding the gears. The narrator knows his son harbors big dreams, which is why he breaks from his normally stoic nature: And I learned not to say much of nothing, so I figured you already know / But in case you don’t or maybe you forgot, I’ll lay out it real nice and slow.

His main fears are that his son will get a bit too highfalutin, a notion illuminated by the iconic first line of the chorus: Don’t call what you’re wearing an outfit, don’t ever say your car is broke. There’s also the fear this kid might forget his roots once he gets out on the road: Don’t sing with a fake British accent, don’t act like your family’s a joke.

Isbell also references John Lennon’s famously infamous line from the ’60s: Don’t tell ’em you’re bigger than Jesus, don’t give it away. In other words, if you grab that brass ring, hold on to it. It’s safe to say that simply the act of writing “Outfit” for Drive-By Truckers shows Jason Isbell heard his dad’s advice loud and clear.

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