Famous Country Singers from Wisconsin

Posted by: Pat Watters
Updated: March 31, 2020

I started singing and playing country music publicly in 1997. I played bars, private parties, weddings, nursing homes… any damn place I could play country music in the great state of Wisconsin, I did. In January 2004, after graduating from University of Wisconsin-Eau Claire, I moved to St. Louis, MO where my girlfriend (now wife) was going to graduate school. And that’s the first time I heard this…

“Wait… where are you from? You’re from Wisconsin and you play country music?”

That’s when I realized. Outside the upper Midwest, people have no idea what life is like up here. I don’t know what they expect. But my Wisconsin is small towns, dairy farms, and tiny bars. That’s country.

Anyways, this got me to thinking. Wisconsin has contributed to country music more than people know. Several of the most prolific country music singers in the history of country music came from Wisconsin. So I decided to create this article highlighting just a few of the most famous country singers from Wisconsin. 


What? Joe Diffie is from Wisconsin? This country singer was a true fixture of the 90s. With hits like “John Deere Green” and “Bigger than the Beatles,” “Prop Me Up Beside the Jukebox” and “Third Rock from the Sun,” Joe and his signature hairstyle kicked butt and took names in the 90s and he was one of my heroes.
But from 6th grade to 11th grade, Joe was a student in Whitehall, WI. Now considered a legend of country music, Diffie is a fixture. While not Wisconsin-born, Diffie’s formative years were spent right here in the dairy state. 

Joe continued to tour the nation delivering stone cold country music to audiences far and wide. In fact,  The Pat Watters Band got to open for him at Camp Douglas Armed Forces Day in 2017. Some people say "never meet your heroes." But he couldn't have been nicer. And he delivered an amazing performance that night as well.


Pee Wee King was born in Abrams, WI, just north of Green Bay. Pee Wee, much like Pat,  comes from a Polka background. His father was a professional polka musician. In the 1930s,

Pee Wee toured and made movies with Mr. Gene Autry. In 1937, he was inducted into the Grand Ol’ Opry. In 1946, while front man of the Golden West Cowboys,  Pee Wee King cowrote “The Tennessee Waltz” with Redd Stewart.

King was a bit of a renegade too. The Opry told him that he couldn’t perform with the drummer and trumpet player he used in his live show. He refused to compromise. He was among the first to introduce drums to the Opry. And later was instrumental in introducing horns, accordion, and the pedal steel guitar the the Opry. His band was also among the first to make on-stage dancing and Nudie suits a part of country music. Forward, Pee Wee King. A true Wisconsin country music singer. 


It’s a shame that when you drive through Spencer, WI, there isn’t a sign that says “Home of Dave Dudley.” You might not know Dave’s name. But you definitely know the HUGE song that Dave wrote. It’s been covered many times. But Dave did it best. I will give you a hint…

“Well I pulled out of Pittsburgh, headed for the eastern seaboard…”

Dave wrote and popularized the country truckin’ song “6 Days on the Road.” The song was covered by a number of artists. Most famously, Sawyer Brown had a big radio hit with it in 1997. 

This dude has the potential and opportunity to be the most impactful country singer to come from the great state of Wisconsin ever. Josh is currently a Show Dog-Universal artist who has charted such hits as “Way Out Here,” “Cold Beer With Your Name On It,” “Beer on the Table,” and “Wanted Me Gone.” 

This Wisconsin county music singer from Cedarburg has the goods. Great singing voice, hell of a songwriter, and a really nice guy.  

Download a FREE Song from The Pat Watters Band

Thanks for checking out our blog! The Pat Watters Band is the 2015 WAMI Country Artist of the Year and a 6-time Wisconsin Area Music Industry People’s Choice Award winning band. Check out our music for free! You can download our breakout song, “I’m Your Buddy,” for FREE.

Check out the video here: