Keller Williams takes an unapologetic, “self-indulgent” approach to performing. 

Through that ethos, he brings the absolute best experience to his audiences with an “if I have fun, they have fun” attitude.

“It’s something that I can’t fake,” he explained. “I take having fun very seriously.” 

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Williams will bring the fun to the base area of Howelsen Hill on Sunday with two sets of music starting at 7 p.m. Steamboat-based Little Moon Travelers will open for Williams at 5:30 p.m.

Williams is no stranger to Steamboat Springs, as he was a resident from 1995 until 1997. During that time, he wrote three songs about the area, including “Sleeping Giant,” “Running on Fumes” and “221 Inches.” 

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“I have a huge love and passion for Steamboat Springs,” said Williams.

He added that he loves the Steamboat free concerts, as it allows for a “super positive vibe.” 

Williams’ music career started in youth and church choir. He built his performance foundation by taking drama and theater classes in high school. At 16, he joined his first band, playing the bass and guitar before transitioning to playing solo and adding electronic loops with a “dance groove” to his performances in college.

The year was 1999 and it was the beginning of Williams’ professional music career. He began touring and has not looked back. He has since averaged 110 shows a year, relying almost solely on “ticket-based pay,” to be able to continue to share his love of music with his growing fanbase. 

Following Tom Petty’s death, Williams began performing with the Hillbenders in what would come to be known as PettyGrass. 

“Both of us, at different times before Tom Petty’s death, had done bluegrass versions of Tom Petty,” explained Williams. “They hit me up to do this Pettygrass thing after he died and that just kept going.” 

He noted that he did not even own a Petty recording. Instead, he listened to songs on the radio, learning the chords and adding his own unique take to what he was listening to. 

Williams had at the time already launched a project of his own, called GratefulGrass, which he enlisted the Hillbenders to become part of.

Bluegrass, according to Williams, melds well with the music of Tom Petty and the Grateful Dead since both exemplify “American songwriting.”

“I think bluegrass was the original dance music,” Williams said.

Williams’ takes on both Petty and the Dead are not always exact renditions of the work of the originals. He often uses the same vocal tempo while double-timing the tempo of the instrumentals. The result is a bluegrass-infused rendition of the original song. 

“There’s only so much you can do to make it your own,” said Williams. “As far as the Grateful Dead goes, that is more of a lifetime soundtrack. It’s pretty much just playing straight to the heart.”

For Williams, the connection with the Grateful Dead is visceral. He still remembers his first Dead show, which he attended in 1987 as a 16-year-old. Between 1989 and 1991, he attended 10 shows every summer before focusing on developing his own music career. Those shows would form the foundation of Williams combining the  “tricks of the trade” of the Dead with his own music. Part of that included moving around extensively to perform on a small budget in a different town every night.

“I incorporated all that I learned in the Grateful Dead world … and put it toward my own life and my own travels,” said Williams. “I have to entertain myself first before I can even hope that anyone is being entertained. It’s something that I can’t fake.” 

Jeremy Campbell, of The Little Moon Travelers, is looking forward to opening for Williams, calling him a “big influence” on his style of playing. As a youth, Campbell recorded Williams’ songs whenever he could and learned his rhythmic style of performing. As a fan of the Grateful Dead, Campbell is looking forward to hearing the way that Williams makes those songs “his own.”

“The music is in me,” said Williams. “I don’t really have a choice whether to play it or not. It has to be played. I love it and can’t do anything else.”

For more information on the Steamboat Free Summer Concerts, visit KeepinItFree.com.