Morgan Wallen Jokingly Reveals ‘The Story Behind My Haircut’ in New Ryl Tea Advert with Caleb Pressley

In a hilarious new clip shared across his socials, Morgan Wallen links up with Barstool Sports comedian, Caleb Pressley, for a mock haircut in promotion of Morgan's Ryl Tea company.

Morgan Wallen kicks off the visuals by wandering into a barber shop, before the receptionist warns him they only have one chair free - and Caleb Pressley will be the one cutting his hair. Morgan is (understandably) hesitant at first, joking, “Last time you shaved all my hair off”, with Caleb responding, “And everyone loved it”.

Morgan shoots back, “Everyone hated it”, referencing the widespread shock from fans when he unveiled his new hairstyle during his Columbus, Ohio tour-stop last year.

One of the many laugh-out-loud moments then arrives when Caleb reassures Morgan, “Trust me, I've gotten better - I just did Kenny Chesney's” - with Kenny famously being bald.

As the skit progresses, Caleb discusses Morgan's The Ryl Company, which he launched in 2023, with the Barstool Sports personality presenting his own version of the drink for the ‘Last Night’ hitmaker to try. He dryly offers his verdict, “That's not as good as mine”, with Caleb then amusingly revealing it's just one of Morgan's that he's scribbled on with a sharpie, drawing a chuckle from the Sneedville native.

“I grew up like probably any other Southern boy, drinking my Mamaw's sweet tea”, Morgan Wallen explains, when delving into the inspiration behind The Ryl Company, before Caleb Pressley blithely cuts him off, “What's a Mamaw? A really old grandma?”

The two are no strangers to being in front of the camera together, with Morgan Wallen appearing on Caleb Pressley's Sundae Conversation video series a couple of times while promoting both his Dangerous and One Thing At A Time albums.

The video was posted shortly before Morgan performed a new unreleased song, ‘Lies, Lies, Lies’, during an intimate writers’ round with HARDY and ERNEST in Nashville.

For more on Morgan Wallen, see below: