At the 2019 NBA Draft, Texas Longhorns prospect Jaxson Hayes rocked a suit-and-hair-matching Sideshow Bob necklace, eventually getting selected 8th overall by the New Orleans Pelicans.

Jaxson Hayes Sideshow Bob Necklace

As a result, we felt compelled to create a list of the most hilarious Simpsons t-shirts found anywhere on the internet. So here we go with our top 10 funniest t-shirts in Springfield (or anywhere else), featuring America’s favorite yellow animated family: THE SIMPSONS!


#10 – Don’t Touch Willie’s Thermostat

SMARCH LEGENDS – Curse lousy Smarch weather in this hysterical t-shirt made by…us! It’s our number 10 funniest Simpsons t-shirt ever, and it’s available here.

Smarch Legends by


#9 – I Stick by My Story! I Be from Jamaica!

SAMSON SIMPSON – The best weed movie of all time - Half Baked - meets the best tv series of all time - The Simpsons! Mash em’ up and what you get is this beauty, available here by BigBadTees.

Samson Simpson by


#8 – When I Grow Up, I’m Going to Bovine University!

RALPH WIGGUM POLO T-SHIRT – The only thing funnier than this tee design is the name of the company that sells it: OLDSHIRTYBASTARD. Any fellow t-shirt purveyor whose name is a play on a member of the Wu Tang Clan is ok by us. Available here

Ralph Wiggum Polo T-Shirt by OldShirtyBastard

#7 – Wud You Say Chief?

BAKE ‘EM AWAY TOYS – Show everyone YOU’RE the chief with this hilarious Simpsons quote t-shirt, made famous by none other than Police Chief Clancy Wiggum. Available here from BigBadTees.

Bake 'Em Away Toys by


#6 – When Bart Simpson Watches Too Much Narcos

ESCOBART T-SHIRT – brings you this hysterical Bart Simpson / Pablo Escobar mash-up t-shirt. It’s Narcos meets The Simpsons in this hilariously funny t-shirt, available here

Pablo Escobart by

#5 – You Told Our Agent This Place Holds Thirty Thousand People!

WE WANT CHILI WILLY – We had thirty thousand people here last night! It’s Red Hot Chili Peppers vs. Moe’s Tavern in this awesome Simpsons RHCP mash-up tee, perfect for your next rock concert! Grab one here.

We Want Chili Willy by


#4 – Mono = 1. Rail = Rail.

MONORAIL MONOPOLY – Pay homage to the greatest Simpsons episode of all time: Marge vs. the Monorail. Also pay tribute to the greatest board game ever: Monopoly. Grab this awesomely hilarious mash-up t-shirt right here, made by the brain trust at BigBadTees.

Monorail Monopoly by


#3 – North Haverbrook…Where the Monorail is King!

MONORAIL IS KING – We’re doing it. We’re going back-to-back Simpsons monorail t-shirts! The episode was so damn good, we made TWO t-shirts paying tribute to it! Available here, and made by the BigBadTees team.

North Haverbrook by


#2 – At Closer inspection, They Are Loafers.

McBAIN – Rainier Wolfcastle just might be the greatest Simpsons character of all time. Our number 2 funniest ever Simpsons t-shirt can be found here.

McBain by


#1 – From Now on You’ll be…Mr. Thompson at Terror Lake.

THE THOMPSONS – We’ve reached the top. This is it. The funniest Simpsons T-shirt on the entire internet. It’s the perfect tee for going into witness protection. And it’s available right here.

The Thompsons by


So that’s that. We’ve paid tribute to not only one of the greatest animated shows of all time, but maybe just the greatest SHOW of all time: The Simpsons.

And just for reading along, we're offering you this special discount code, good for 10% off your entire order! Simply use code SIMPSONS10 at checkout to claim your discount.

We hoped you like our picks. To the show that’s been on for 30 years, here’s to hoping for 30 more!


Bye for now.




  • Brooks Scott on

    McBain should be number 1

    - Simpsons Fan

  • RalphyBoy on

    I sleep in a drawer

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