Wylie Gustafson was born in 1961, the youngest of five kids (all of whom arrived within a seven-year period) in a close-knit, tight-bonded family. His father, Rib Gustafson, a horse veterinarian and all-around horseman, instilled in his whole brood a love of rodeoing and ranching.
“Conrad, Montana, was my world,” recalls Wylie Gustafson, a 2020 inductee to the Montana Cowboy Hall of Fame. “I grew up in that culture. And there is so much to do in this part of the country. Summer time, it was a little bit of everything, including our annual pilgrimage into the Bob Marshall (Wilderness) for six days on horseback, where we would go in for days without seeing another soul. We’d fish and goof off. Those are some of the most poignant memories I have growing up.”
In 1971, the Gustafsons purchased ranch property on the Two Medicine River, a tributary of the Marias River, and Wylie and his siblings found it to be the premiere location to wholly experience the outdoors, especially summer. Rib fly-fished way before it became cool. Fly-rod and a few baloney and bread sandwiches in tow, Rib and the kids would ride on horseback through the herds of livestock and settle in at the river. The clan would spend summer afternoons and evenings sprawled under the immensity of Big Sky blue and white.
There was another aspect of life to which Rib and his wife Patricia exposed the children: the oral, communal, and familial bonding provided by music. On weekends the Gustafson pack would huddle around the television and watch the Lawrence Welk show. When it concluded, Rib would promptly turn off the set, grab a Martin D-18 and croon a bunch of traditional cowboy and folk songs.
“Dad had a sense of humor, so he’d sing funny songs and offbeat folk songs. That’s where it started. Sundays in church, Mom would play the piano, and she would sing along with dad. It was our way of celebrating and spending family time. We were four brothers and one sister, and we’d dance and sing ‘Skip to My Lou’ with our sister. Rib had a unique taste in music, quirky old folk songs he loved to sing. I’ve never heard anyone else sing these songs but him.”
Such impressions weren’t lost on the Gustafson boys, specifically Wylie and Erik (aka Erik “Fingers” Ray), who formed a band in high school called the T-Birds, covering loads of Muddy Waters and Johnny Winters tunes, as well as the music of the day such as ZZ Top and the Rolling Stones and Beatles.
Recalls Wylie: “We decided that we’d go to college and go be a pop or rock band, and we figured that we could make money on the weekends doing it.”
After adding another member, Wylie and Erik played just about every weekend at various clubs in Missoula, even winning the “Battle of the Bands” at The Wilma two years in a row.
In the spring of 1981, the boys picked up an agent, who told them that if they (the foursome had reorganized as “The Time”) dropped out of college, there would be enough engagements to keep them busy full-time.
“Our first two weeks we were sent to the Winter Circle in Cut Bank,” says Gustafson. “The manager was an older lady who didn’t take any crap from bands, and I think our agent wanted to see if we could last two weeks there. If we could last two weeks there, we could most likely last a long time. From then on, we went six nights a week, four hours a night. Throughout the 1980s, I think we only had about three or four weeks off a year.”
In 1986 Wylie moved to Los Angeles to pursue a record deal and take the next leap; there was a band and a publicity stunt on every corner, so he reached back into his humble classic country roots and expended more time songwriting.
A quirky thought perhaps provided Wylie with his musical breakthrough while he lived in Los Angeles in the 1990s. Back in the days when Rib had taught him the brass tacks of horseback riding, the old man would yodel. Rib would yodel on the summit of the ski hill. He would yodel when he was at his happiest. As a kid, Wylie would yodel to mimic his father or to just be quirky or even to show off for his buddies. But one night at a club in one of the largest cities in the world, a country kid from north-central Montana yodeled once again. This time, he did it to capture the attention of a murmuring, distracted audience. It worked.
“LA people can be indifferent and burned out on so many bands, so I yodeled a song,” recalls Gustafson. “By gosh, they sat down their drinks and they actually listened. I realized the power of yodeling. Right afterwards, I met an old-timer who had a section of vinyl records of yodeling, and he pointed me towards it. From then on, I approached it as a serious art form – especially the fancy cowboy-style of yodeling.”
Wylie yodeled commercially for companies such as Mitsubishi, Miller Lite, Taco Bell, and Porsche, and by the time that a fledgling company named Yahoo! contacted him, he had already been rolling his vocal cords in such a manner for five years.
The session with Yahoo! in 1996 was over in perhaps 15 minutes and in about as many takes. It seemed like any other gig until the moment Wylie heard his bellowing voice during a Super Bowl commercial three years later.
“It was kind of a shock for me,” recalls Gustafson. “It started off as a regional commercial and it became Yahoo’s audio logo and part of their email. They were pushing these ads out there worldwide. It was quirky enough and it worked with their ad campaign and their image, and the timing was just right.”
Public appearances yodeling at fairs and festivals followed, and Wylie even emceed an amateur yodeling contest that Yahoo! brought to eight cities nationwide as part of its promotional branding campaign.
“I’ve spent all of my life trying to write that three-minute classic country radio song,” chuckles Gustafson, “and it’s funny how life will make a fool out of you sometimes. Fame came not with the three-minute song, but with the three note song.”
After a successful run with Rounder Records, Wylie returned to Conrad in 2009, where he spent quality time with his aging parents. (Patricia died in 2012; Rib in 2014).
“Conrad has basically been reduced by half in population. The classrooms are now with 40 kids in them, and when we were in school, we had 80 classmates. The population has dwindled but the community still does all right.”
Wylie says that having such a rural base has left him with fewer gigs and corporate events, but that he is willing to compromise and sacrifice to help raise his three children in the same place where he fashioned his own character.
“I love the smallness of Conrad, the community, and the people,” says Gustafson. “It feels like home to me. I’ve traveled the world. But I really believe that Conrad has everything that I need.”
His Montana engagements take place in the teeniest of settings; yet these events often guarantee the most earnest connections.
“Two Dot hires us for its fire department fundraisers. We end up in these little communities, like at the Stanford Stampede (population currently less than 400; his mother, Patricia, grew up in Stanford). Ranch families come because we speak to them. We want the music to resonate with ranching and farming communities.”
—Brian D’Ambrosio
Check out what Wylie's up to at his official website at Wyliewebsite.com.