The Many Odd Jobs Of Willie Nelson

Willie Nelson country music

I’m a firm believer that our early jobs shape our worldview much more than we give it credit for.

The experience of seeing stores from the other side of the cash register, pouring instead of ordering beers, picking orders and packing boxes, and whatever other random thing you did for cash while young sticks with you long into your life, and I believe for the better. It’s easiest to see this when you go out to eat with someone who never worked in a restaurant and they treat the server like a servant…

While we may look at the end result of celebrities and assume they’ve always been in the higher echelons of society (and let’s be honest, there’s more than a few nepo-babies out there riding the wave of good fortune), there’s a solid chance that the names we now hold in high regard at one point or another were themselves working some strange job to pay the bills.

In the country music world, I’m sure I can pick an artist out of a hat and find a ton of surprising things they’ve done, but one who really seems to have done a little bit of everything is Willie Nelson.

The proud Texan moved around a bit when he was a kid, and while he always had dreams of making it in music, he was far from an overnight success and struggled his way up the ladder until he just so happened to run into Patsy Cline’s husband at Tootsies one night and the rest, as they say, is history.

But before Shotgun Willie released Red Headed Stranger and became the living country music legend that he is, he was just a no-namer floating around trying to rub a few pennies together.

In no particular order, here’s some of the odd jobs Willie Nelson took over the years to support himself while making music.

Bible Salesman

If the words “Willie Nelson” and “Bible” ring a bell, it may because he was known to shoot a few copies of the Good Book while on tour. You can read all about that story here.

Cotton Picker

During hot Arkansas summers of the early 1930’s, the Nelson family would bolster the family income by heading out to the fields and picking cotton. While he was forced to do it a bit, Willie hated it and soon took jobs performing in local honky tonks to earn his share for the family.

Door to Door Vacuum Salesman

Imagine opening your front door to a suave (and probably stoned) Willie Nelson with a brand new Hoover in hand… I’d have bought one for sure and if my wife was home alone when he came knocking, well I may have come home to an empty house with a note saying she ran off with him.

Saddle Maker

Can’t be a cowboy without a horse and you can’t ride a horse without a saddle. Shoutout to Willie for keeping the gunslingers seated.


The most unacclaimed, but important, role in a restaurant. Most of the time it’s some underpaid and overworked high school kid, but someone’s got to make sure the glasses, plates, and silverware are clean and available.

Autohouse Partsman

Need a new head gasket, fan belt, control arm, or U-joint? Willie had you covered after dropping out of Baylor University in 1956.

Nightclub Bouncer

Willie may not be the biggest man on the planet, but don’t let his 5’6″ height fool you. He has 5 different blackbelts, including in taekwondo and GongKwon Yusul, so you probably won’t even know what hit you before you’re getting dragged out the back after causing trouble at one of Willie’s bars…

Disc Jockey

While it may be odd to think of today, back in the day it was actually somewhat common for aspiring artists to start working with a radio station in hopes of being discovered. Willie took his first disc jockey job in Pleasanton, Texas with almost no experience but wound up working for numerous stations in the Lone Star State and Pacific Northwest.

Sunday School Teacher

Country star by night, man of God by day.

While he was DJing in Fort Worth, Nelson found another way to earn money by teaching Sunday School to the local children. Religion was a large part of his childhood and the first songs he learned to play were Gospel songs, so while it may not jive with his “outlaw” persona, it makes a lot of sense in the context of his early life.

Tree Trimmer

Willie was actually a tree trimmer at two different points in his life. The first was in high school and the second was after dropping out of Baylor. I’m sure there’s a joke here about “trees” and “being high”, but I’ll let you come up with one on your own…

Relief Phone Operator

Of all his odd jobs, this is probably the one that drove him to the green stuff. Hours on end answering phone calls, making connections, potentially answering questions from the unhinged public, no wonder he wanted something to knock off the edge…

Pawn Shop Employee

The sheer number of characters one can meet working at a pawn shop had to lead to more than a few ideas for songs, but I can’t see Willie being a hardliner on price, which may be why he didn’t stick with it for that long.

Sales Manager for Encyclopedia Americana

Looks like Willie did such a good job selling vacuums and bibles that the first general encyclopedia to be published in North America wanted him leading a sales team. Not going to lie, I miss going to someone’s house and them having an encyclopedia set on the shelf. Sure, the internet is way better, but flipping one of those bad boys open and learning about some random piece of history was a truly great experience.

Guitar Instructor

Like DJing, this one makes sense. Why not teach people a few chords for extra cash, how hard can it be?

Okay, I play guitar a bit myself and absolutely hate when someone asks me to teach them, so kudos to him for being willing to do it.

A beer bottle on a dock



A beer bottle on a dock