During his senior season in 1998, running back Matt Rupnow ran for 2,112 yards and 25 touchdowns, helping the Cheesemakers go into a deep playoff run.

A co-captain, Rupnow was named the team’s Most Valuable Offensive Player, as well as a unanimous All-Badger Conference pick, All-Region and first-team all-state by the Wisconsin Football Coaches Association. He was named a player in the 1999 Shrine Bowl.

“My fondest memories of prep athletics were the community spirit and the sense of camaraderie — just being with the guys and the families,” Rupnow said.

While his skills had been showcased on the gridiron in high school, football didn’t hold his heart.

Instead, his passion was music. 

“My career path has been a long and winding road,” Rupnow said. “I guess I realized I wanted to be a singer-songwriter when I did a speech in Mr. Trampe’s speech class about Bob Dylan’s ‘Blowin’ In the Wind.’”

After graduation, Rupnow briefly played football at Luther College in Decorah, Iowa, but his path in life led him to plucking his six string for a living.

“I quit music briefly after my first band The Huber Music Co. parted ways,” Rupnow said. “I just could never shake the music bug, but after I moved to Durango, Colorado, in 2007, I started writing again.”

Rupnow had played roles in musical productions in high school, but once he left southern Wisconsin, he was headed into strange waters and away from the familiar faces he grew up with.

Durango, in southwest Colorado, is where Rupnow calls home these days, but he works and plays gigs all throughout the Four Corners region. 

“Durango is very transient and kind of elitist, the sense of community isn’t the same as the Midwest. People are active and nice, but it’s different,” Rupnow said. “I chose the Four Corners after coming out here on a trip around 2003. I loved it for the deserts, the mountains, the ancient Anasazi ruins and just being able to explore the southwest. To say it’s a vast, ever-changing landscape is an understatement.”

The Four Corners region is where Colorado, Arizona, Utah and New Mexico all meet.

“It’s also over four hours to the closest interstate, and it borders the Weminuche Wilderness area that is the biggest wilderness area in the lower 48 (states),” Rupnow said. “You can go 100 miles in the Weminuche in the heart San Juan Mountains and not see a road. It’s an outdoor enthusiast’s paradise.”

He spent about five years touring the country with the band DL Marble, which was based out of Tempe, Arizona. While glad he “went for it,” Rupnow admitted those years “were hard,” especially with his son, Ryder, just being born. Ultimately, he separated from his bandmates.

“Those fellas weren’t the sort of guys I wanted to be around or lend my energy to anymore,” he said. “Now I’m doing my own solo stuff and getting tons of local gigs and my whole life seems to be heading in a better direction.”

Although most of his current work is solo items, Rupnow plays in a band called Red Eyed Djinn. He’s worked a variety of odd jobs over the years to supplement his income, and that has had a hand in leading him to where he is currently at in life at almost 40.

“I’ve done all kinds of odd jobs from building houses to working as a cook, waiter, assistant brewer. I’ve done delivery driving jobs all over the Four Corners area,” Rupnow said. “The most important lesson I’ve learned in life is to try and find your Zen. It’s how you react to things, because bad things are always going to occur.”

Recently he started his own record label, Woodyfink? Productions, in honor of his late friend and MHS graduate Dan Marchant. “The name was his idea,” Rupnow said.

With the label, Rupnow has been hired by two musicians for production work. “I’ve taught myself how to finish the whole process of mixing and mastering during quarantine,” he said. 

He’s released two albums already this year — the first on April 20, and the second June 9. “Now gigs are starting back up.”

Rupnow said his favorite venue to play over the years has been Rocky Point in Mexico.

“I’ve recorded albums in New York City and Los Angeles. I’ve done cross country tours — the longest was a five-week tour from Tempe, Arizona, to Rochester, New York,” Rupnow said.

He’s toured Texas multiple times remembers renting an Air BNB while playing some of the iconic venues in Austin.

He makes it back to Monroe a couple of times each year — “if I’m lucky” — to see his parents, Steve and Cindy Rupnow, with Ryder, now 7, in tow. 

“I love Wisconsin’s natural beauty. It’s just as beautiful in its own way. It’s so green in lush and it’s nice to get out of the drier environment sometimes,” Rupnow said. 

While the path of his career has had more twists and turns in it than a mountain road in the Rockies, he doesn’t plan on changing his tune anytime soon. 

“There has been a steady stream of moments leading me to where I am at now. It took a while for me to get here, but I have more focus and clearer sense of my vision,” Rupnow said.