A native of the Four Corners region, Kyle Rightley is no stranger to crossroads. A trained classical musician with a jazzman’s flare for improvisation and a folk singer’s love of storytelling, Kyle stands at a unique junction. Currently residing in Madison, Wisconsin, he has built a career as a singer/songwriter, multi-instrumentalist, educator, and all-around musical chameleon.

His third acoustic solo release, Making Home, won the 2018 Madison Area Music Association Award (MAMA) for Country/Bluegrass Album of the Year. John Noyd of Maximum Ink said the album “casually conjures rolling, green pastures and lonely, late-night interstates.” The lyrics draw upon personal experiences, nature, and current issues, “all rooted in traditional Americana that resembles political forebears like Joan Baez or Willie Nelson” (Isthmus).

Though his primary instruments are guitar and low brass, Kyle can also be heard playing keyboards, concert bells, mandolin, ukulele, percussion, electric bass, and just about anything he can get his hands on. He won MAMA awards for trombone player of the year and euphonium player of the year in 2021 and 2020 respectively. In addition to his solo exploits, Kyle is a member of award-winning groups The Big Payback, Driveway Thriftdwellers, The Civil Engineers, Five Points Jazz Collective, Don’t Mess With Cupid, and other area ensembles. He also contributes regularly as a songwriter to the Warrior Songs compilation albums. His 2021 song “Seawolf 7-6,” from the album Warrior Songs, Vol. 3, was featured on CNN’s The Human Factor. 2016’s Warrior Songs, Vol. 1 contained Kyle’s song “Brothers.” Rick Tvedt of Local Sounds Magazine praised the song for its “dark subject matter” and “powerful production,” calling it “one of the album’s strongest.”

Rightley’s bands have won multiple awards across a variety of genres. Driveway Thriftdwellers won the MAMA Country/Bluegrass Album and Song of the Year awards in 2019. The Civil Engineers’ second album, #, was named the 2018 Pop/R&B Album of the Year by the same association. In 2017, The Big Payback, Driveway Thriftdwellers, and Beefus won MAMAs for Jazz Album of the Year, Country/Bluegrass Album of the Year, and Rock Album of the Year, respectively. Kyle penned the song “Running with the Fire,” which won the 2017 MAMA award for Rock Song of the Year and was called a “rise-up anthem” by Isthmus. The year also saw Driveway Thriftdwellers win the Wisconsin Area Music Industry (WAMI) award for Country Artist of the Year, and their album Cutover Country was chosen as one of the “10 best Milwaukee albums of 2016” by the Milwaukee Journal Sentinel.

Kyle’s earliest musical memories involve annoying his parents by singing Neil Young songs way too loud while pounding on the stairs. “I would also draw album covers and make up song titles to go on the back jacket” recalls the musician with a smile. “Sometimes it feels I fell into being a singer/songwriter by accident, and sometimes it feels like I planned it all along.”