Esteban – Bachelor Uncle of the Week

Look at this fucking goofball.

Editor’s note: I have done zero research for this article. Everything I say is 100% made up and probably definitely true.

Sometimes Bachelor Uncle’s have a lack of self awareness. Some people find it easy to be confident when they don’t look at themselves critically. Esteban is a giant goofball weirdo who turned a stupid hat and glasses into a long and illustrious career.

Best known for selling garbage guitars for “OK” prices to attention starved grandmas on QVC, Esteban has built an entire empire. For this, he must be commended. But his whole vibe just screams eccentric weirdo.

Meet Esteban. Middle Manager.

In 1975 Stephen was just a middle manager at the corporate headquarters of Gymboree. He was trying to figure out how to get Christina in receivables to notice him. He heard that women love guys who play guitar so he started researching.

Research was not easy before the days of the internet, so Esteban had to go to libraries and talk to real people. On the back of an old Jack Kirby comic book was an advertisement touting the opportunity to learn classical guitar with the wisened teacher Segovia. So he signed up.

Segovia couldn’t care less about this dumpy dude and just kept calling him by the wrong name. Probably hoping he’d move on. And that is how Stephen became Esteban – the Lady Killer.

This woman is not real. She is a hologram cast out of the spells that Esteban casts with his 80 dollar guitars.

On his way back from Europe, he was struck by a car and lost the use of one of his arms and an eye. Knowing that Christina would never take him like this, he squirreled himself away and began the epic task of reinventing himself. Using his classical guitar skills gifted to him by the Master, he nursed himself back to health.

He donned a Zorro hat and dark sunglasses to hide the scars of his accident and slowly the legend grew. Tales were told of a flamenco shirted weirdo who wore sunglasses all the time and could make women appear out of thin air.

Eventually word reached the hallowed halls of the QVC corporation and they knew they needed to sign Esteban to a deal.

If you touch the guitar like this, your sadness becomes a balloon you can pop.

So Esteban is a real life super hero who does very little with his power. But all things considered, his guitars aren’t the worst you can buy. They’re surprisingly playable (after getting a professional set-up) and his packages are thoughtfully put together. They come with the guitar, a strap, picks, a case, and many DVDs full of hours of Esteban teaching you how to play the guitar.

He’s definitely not ripping people off. He’s just being weird. For decades. On TV. For everyone to see. And I love it. I love seeing him, fully committed to this strange guitar hero character, teaching everyone about how easy guitar is.

It’s not. But he thinks it is. And his guitars get stupider and stupider every year. They started out as just basic acoustic and classical guitars. Now every single one is a “limited edition” that is individually numbered. But each series is “limited” to 25,000 units, so there are more guitars than there are buyers.


Last decade someone introduced Esteban to a bedazzler and his guitars have never been the same. They’re covered in little gems and jewels. Weird custom paint jobs. Partnerships with Chevy and Cadillac to produce weird Camaro and Eldorado guitar models (Cadillac hasn’t made an Eldorado since 2002, but, Esteban put out a Cadillac Eldorado guitar in 2007).

This blog really focuses on people and things I find unique, interesting and strange. It likes to focus on characters and people that I find compelling. Esteban is a compelling character. Without his “schtick” he’s just another aging boomer guitarist at open mic night. But a puffy shirt, hat and glasses turn him into a millionaire known all over the world.

Esteban needs to get a better fontologist.

And he’s smart too. He doesn’t market to guitar players or other musicians. They’d see through his ruse. No he markets to old ladies and out-of-touch lesbian aunts. He markets to weird dudes in Iowa who love Boomer Rock. He offers the promise of a fantastic life where you are the center of attention and you wow the world with your talent and personality. He sells the fantasy that if a creepy 60 year old, overly tan grifter can become a sexual icon, then you can too.

Esteban is hope.

And for that reason, He’s the Bachelor Uncle of the Week. Let’s get that weekend, baby!

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