A fan of T. Texas Tyler, Phillips adopted the stage name U. Utah Phillips.
Phillips met folk singer Rosalie Sorrels in the early 1950s, and remained a close friend of hers. It was Sorrels who started playing the songs that Phillips wrote, and through her his music began to spread. After leaving Utah in the late 1960s, he went to Saratoga Springs, New York, where he was befriended by the folk community at the Caffé Lena coffee house, where he became a staple performer throughout that decade.
Phillips was a proud member of the Industrial Workers of the World (IWW or Wobblies). His view of unions and politics were shaped by his parents, especially his Mom who was a labor organizer for the CIO. But Phillips was more of an Christian anarchist and a pacifist, so found the modern-day Wobblies to be the perfect fit for him, an iconoclast and artist. In recent years, perhaps no single person did more to spread the Wobbly gospel than Phillips, whose countless concerts were, in effect, organizing meetings for the cause of labor, unions, anarchism, pacifism, and the Wobblies. He was a tremendous interpreter of classic Wobbly tunes including "Hallelujah, I'm a Bum," "Preacher and the Slave," and "Bread and Roses."
An avid railfan, Phillips recorded several albums of music related to the railroads, especially the era of steam locomotives. His first recorded album, Good Though!, is an example, and contains such songs as "Daddy, What's a Train?" and "Queen of the Rails" as well as what may be his most famous composition, "Moose Turd Pie" wherein he tells a tall tale of his work as a gandy dancer repairing track in the Southwestern United States desert.
In 1991 Phillips recorded, in one take, an album of song, poetry and short stories entitled I've Got To Know, inspired by his anger at the first Gulf War. The album includes "Enola Gay," his first composition written about the United States' atomic attack on Hiroshima and Nagasaki.
Phillips was a mentor to Kate Wolf. He recorded songs and stories with Rosalie Sorrels on a CD called The Long Memory (1996), originally a college project from 1992 'cold-drill Magazine' Boise State University. Ani DiFranco recorded two CDs, The Past Didn't Go Anywhere (1996) and Fellow Workers (1999), with him. He was nominated for a Grammy Award for his work with Ani DiFranco. His "Green Rolling Hills" was made into a country hit by Emmylou Harris, and "The Goodnight-Loving Trail" became a classic as well, being recorded by Ian Tyson, Tom Waits, and others.
Phillips was a member of various socio-political organizations and groups throughout his life. A strong supporter of labor struggles, he was a member of the Industrial Workers of the World (IWW), the International Union of Mine, Mill, and Smelter Workers (Mine Mill), and the Travelling Musician's Union AFM Local 1000. In solidarity with the poor, he was also an honorary member of Dignity Village, a homeless community. A pacifist, he was a member of Veterans for Peace and the Peace Center of Nevada County.
In his personal life, Phillips enjoyed varied hobbies. These included Egyptology; amateur chemistry; linguistics; history (Asian, African, Mormon and world); futhark; debate; poetry; and gardening. He also enjoyed culinary hobbies, such as pickling and cooking.
He married Joanna Robinson on July 31, 1989, in Nevada City.
Phillips became an elder statesman for the folk music community, and a keeper of stories and songs that might otherwise have passed into obscurity. He was also a member of the great Traveling Nation, the community of hobos and railroad bums that populates the Midwest United States along the rail lines, and was an important keeper of their history and culture. He also became an honorary member of numerous folk societies in the U.S.A. and Canada.
When Kate Wolf grew ill and was forced to cancel concerts, she asked Phillips to fill in. Suffering from an ailment which makes it more difficult to play guitar, Phillips hesitated, citing his declining guitar ability. "Nobody ever came just to hear you play," she said. Phillips told this story as a way of explaining how his style over the years became increasingly based on storytelling instead of just songs. He was a gifted storyteller and monologist, and his concerts generally had an even mix of spoken word and sung content. He attributed much of his success to his personality. "It is better to be likeable than talented," he often said, self-deprecatingly.
Until it lost its funding, Phillips hosted his own weekly radio show, Loafer's Glory: The Hobo Jungle of the Mind.
Phillips lived in Nevada City, California for 21 years where he worked on the start-up of the Hospitality House, a homeless shelter, and the Peace and Justice Center. "It's my town. Nevada City is a primary seed-bed for community organizing."
In August 2007, Phillips announced that he would undergo catheter ablation to address his heart problems. Later that autumn, Phillips announced that due to health problems he could no longer tour. By January 2008, he decided against a heart transplant.
Phillips died May 23 in Nevada City, California, from complications of heart disease, at the age of 73. He was survived by his wife, sons, Duncan and Brendan, and a daughter, Morrigan. Following a private service, a public memorial was held on June 1, in Pioneer Park, in Nevada City. His service was officiated by Meghan Cefalu, a Unitarian Universalist pastor. The night he died local newspapers reported an unusual thunder storm. Those close to him remarked that he rode out of town on a bolt of lightning.