Along with her guitar, she galvanized teachers to strike for better education funding, paving her way to the presidency of the Utah Education Association, and eventually, an unsuccessful bid for Congress.
Eskelsen still sings out her views on education, but from a more prominent platform.
In 2003, she defeated a trio of opponents to become secretary-treasurer of the National Education Association, the nation's largest teacher organization. She now lives in Washington, D.C., with her husband, Ruel, and gives motivational talks throughout the United States.
Tuesday, Eskelsen was elected by acclamation to a second three-year term in the NEA's third-highest office. The job is flashier than her first one in education - as a "school lunch lady," but Eskelsen remains unassuming and plain-spoken. She still strums her guitar on occasion, providing back-up for her pithy songs about education issues. Her current favorite tweaks a federal education-reform law for "testing the butts off American kids."
It's called "No Child's Behind Left."
Eskelsen's parents met in Panama when her father was stationed there as a soldier; her mother is Panamanian. She grew up in Texas, Georgia, Washington, Alaska, Colorado and Utah. After marrying at 18, she took a job in the lunchroom of a Head Start program at Fort Carson, Colo., where her soldier husband was stationed.
"I wanted to work around kids, and I wasn't qualified to do anything," Eskelsen said.
The lunchroom job led to a position as a kindergarten aide. After watching Eskelsen work with the children, the classroom teacher encouraged her to become a teacher.
"It was the first time in my life anyone had suggested I might want to go to college," she said. "It was not an expectation for me."
After returning to Salt Lake City, Eskelsen earned an elementary education degree, magna cum laude, at the University of Utah; she and husband Ruel performed as folk singers to pay her way. Later, she received a master's degree from the U. in instructional technology. She taught elementary grades for nine years before being named Utah Teacher of the Year in 1989. In 1990, Eskelsen won the UEA presidency and led feisty battles for education funding during the governorship of Norm Bangerter.
"UEA was able to do good work on a bipartisan level with a very conservative governor who had not been impressed with the things on our agenda," Eskelsen said.
She is proud that class sizes were reduced during her tenure but annoyed that "Utah still has the highest class sizes in the galaxy."
Under her leadership, UEA won fights to provide money for teacher supplies and a lawsuit over state trust lands.
"Those lands have to be managed for the benefit of public schools, to produce income," she said. "We had incredible wins, and we are still seeing the results."
Utah Senate President John Valentine remembers Eskelsen's years on Capitol Hill and her skirmishes with conservative lawmakers.
"I took an immediate liking to her because she was frank and forthright with her opinions, though we didn't always agree," Valentine said.
Valentine still chuckles at the memory of humorous barbs Eskelsen tossed out when lawmakers disagreed with her, and the backlash they sometimes caused.
"Everyone remembers Lily Eskelsen and her guitar," he said.
In 1998, Eskelsen ran as a Democrat for Congress against incumbent Republican Merrill Cook. The Eskelsen campaign's use of unflattering photos, which Cook attributed to a "bad hair day," became a major campaign issue. Eskelsen's loss, by a wide margin, was attributed by some to the rancor of the campaign.
"She is very bright and very articulate," Cook said. "But I think she is too liberal for the Utah electorate. She got trapped into running a bit of a negative campaign, and that backfired. We have a 180-degree difference on the issues, but she is certainly a worthy articulator of her positions."
Eskelsen still keeps an eye on Utah politics and weighs in on hot-button issues, such as debates over private-school vouchers.
"How can we take the meager funding we give public schools and share it with private schools?" she asks. "Who on what planet thinks this is a good idea?"
She's just as voluble on federal education policy, especially where the No Child Left Behind Act is concerned.
"I have a real hard time being polite," she said. "The way they have enacted this law, it's as dumb as dirt. It's the stupidest thing I've ever seen - and I'm holding back."
But not much. Eskelsen's willingness to let her passion show is her special gift, said Pat Rusk, UEA president.
"She has a way of taking complicated issues and presenting them in such a way that we all get it," Rusk said. "She reaches people the way a teacher reaches them. She deals with very important issues, but she always finds some humor in them."