Country music’s funny man?

For nearly two decades, Brad Paisley’s won praise from critics and country fans for his sharp wit and lighthearted songwriting approach.

He’s known most as a country star—with 11 studio albums, numerous chart-topping hits and three Grammys tucked neatly under his buckle—but a well-established music career hasn’t kept the West Virginia native from exploring other avenues: a book of fishing stories, a self-starring stint on the CMT’s Nashville, lots of celebrity judging and … South Park?

Paisley did sing alongside Cartman in a 2012 episode, and that’s just the tip of his comedy endeavors. He’s hosted shows at the Nashville Comedy Festival, and last year, he released his own Netflix special, Brad Paisley’s Comedy Rodeo, a night of six comics that included Sacramento’s Mike E. Winfield.

“Many of his fans would call him hilarious,” said Winfield, our comedy-and-Paisley expert. “Backstage, he’s a fun guy, and you can tell he’s intrigued by the science of comedy.”

In Comedy Rodeo, Winfield dissects the guitar-slinger’s hit “I’m Gonna Miss Her.” The song centers around Paisley’s choice to spend the day fishing, rather than salvaging his deteriorating relationship with a woman. Winfield explores the same hypothetical in his own relationship, and the consequences (her reaction is less-than-enthusiastic).

From Paisley’s on-set reaction, he seems to have a good sense of humor.

“He loved the bit, and he definitely let me know he wanted it in the special,” Winfield recalls. “It was funny because he thought I made the joke right there on the spot when he first saw it. I just told him I did.”

When it comes to humor in Paisley’s music, look for his more playful tunes; “The Cigar Song” is a compelling fable about a con artist with a penchant for, well, cigars; “Online,” a plucky, upbeat bluegrass tune that pokes fun at fake internet personas; and “I’m Still a Guy,” wherein Paisley conflates plucking your eyebrows and practicing basic skincare with forfeiting your masculinity and “lining up to get neutered.”

Generally speaking, the icon’s vast catalog ranges from delightfully clever to, at times, head-scratchingly heteronormative.

He’s provided plenty of fodder to seasoned satirists, too. When his 2013 song “Accidental Racist” made headlines for its lyrical clunkiness and failed attempt to tackle the nuance of American race relations, shows like Saturday Night Live and The Colbert Report quickly took a whirl at lampooning the Paisley and LL Cool J duet. For reference, Paisley sings about not wanting to be judged for wearing a Confederate flag T-shirt, while LL Cool J raps: “If you don’t judge my gold chains / I’ll forget the iron chains.” The general consensus among comedians and critics alike was that this song should have never been written.

Despite past debacles and split debates on his comedic sensibility, Paisley is most in his element when singing earnestly about the simple pleasures of steering a mud-spattered truck, the hardships of the working class or the soul-crushing despair of a broken relationship.

“There’s a lot of sides to his music,” Winfield explains, “so if you’re a fan of country music, there’s something in there for everyone.