"The worst job I ever had was ironing cowboy shirts.…

“Howdy pressing” is a pun for “how depressing.”

“There’s nothing sadder than a cowboy saying hello to his ironing. Howdy pressing” was posted on X/Twitter by Tom Fox on May 29, 2013. “The worst job I ever had was working in a factory making cowboy records. Howdy pressing” was posted on X/Twitter by Matt Ward on October 29, 2013. “Worst job I had was ironing cowboy shirts. Howdy pressing” was posted on X/Twitter by 🌋SouthernMrsOwen🌋 on December 13, 2016. “The worst job I ever had was ironing cowboy shirts. Howdy pressing” was posted on Facebook by Home Groan Puns - David Mulberry on October 15, 2025.

“I quit my job crushing cans. It was soda pressing,” “My job testing fizzy drinks is really getting to me. It’s soda grading” and “I used to work in a shoe-recycling shop. It was sole-destroying” are similar puns about work.

X/Twitter
Tom Fox
@TomFoxTom
There’s nothing sadder than a cowboy saying hello to his ironing. Howdy pressing.
3:58 PM · May 29, 2013

X/Twitter
Matt Ward
@hotsnax
The worst job I ever had was working in a factory making cowboy records. Howdy pressing.
11:58 AM · Oct 29, 2013

X/Twitter
Dr Faustus
@PUNderbeard
The worst job I’ve had was ironing cowboy clothes…howdy pressing…
2:57 PM · Oct 29, 2013

X/Twitter
⑦ANDO⑦
@anderspoon
“@sickipediabot: The worst job I ever had was working in a factory making cowboy records.
Howdy pressing. (via Matt Ward)”
@MattWardUK ???
3:11 PM · Oct 29, 2013

X/Twitter
Short Bloke Josh!
@ShortBlokeJosh
I once had a job making cowboy badges…
Howdy Pressing
6:12 PM · Oct 31, 2013

X/Twitter
Sarah Tagiteu
@sarah_Isla92
“@Martin1Williams: Most boring job I ever had was in a Texas factory making cowboy records. Howdy pressing. ” #badsundayjokes
8:35 AM · Nov 24, 2013

X/Twitter
Mark Haggan
@markhaggan
Worst job I’ve had was ironing shirts for cowboys. Howdy pressing.
Ironing jokes… http://bit.ly/IroningJokes
@hi_robb
3:00 PM · Aug 28, 2015

X/Twitter
🌋SouthernMrsOwen🌋
@SouthernMrsOwen
Worst job I had was ironing cowboy shirts. Howdy pressing.
2:23 PM · Dec 13, 2016

X/Twitter
Sandra Velázquez
@SandyVelazqz87
RT dadtellsjokes: Worst job i had was ironing cowboy shirts.
howdy-pressing.
6:22 PM · Aug 25, 2017

X/Twitter
Puns AndOneliners
@punsandoneliner
Worst job I had was ironing cowboy shirts. Howdy pressing.
http://markhaggan.com/randomness/ironing-jokes/
#Ironing #Joke #Humour #IroningJoke http://markhaggan.com/randomness/ironing-jokes/
11:00 AM · May 21, 2018

X/Twitter
mariana Z
@mariana057
The first job I ever had was ironing cowboy clothes.
Howdy pressing…
11:20 AM · Jul 28, 2021

Reddit—Dadjokes
Firegoat1—April 11, 2022
Worst job ever
A guy walks into a bar and orders a beer. “So what’s the worst job you’ve ever had?” the bartender asks him. “I guess that would be when I worked for a dry cleaners down in Texas. All I did all day long was iron a bunch of starched-up western shirts and jeans for cowboys,” the guy says. “Howdy pressing.”

Facebook
Home Groan Puns
David Mulberry ·
October 15, 2025 at 10:55 AM ·
The worst job I ever had was ironing cowboy shirts.
Howdy pressing.
😂😂

X/Twitter
LaffGaff
@LaffGaff
The worst job I ever had was ironing cowboy shirts.
Howdy pressing.
#funny #jokes #dadjokes #dadjokesdaily
https://laffgaff.com/funny-joke-of-the-day/cowboy-shirts-joke/
10:02 AM · Oct 18, 2025