Vermont's beloved musician, Jon Gailmor, left this world with a smile, just as he sang about in his iconic song, 'I'm Gonna Die with a Smile If It Kills Me'. This poignant story, penned by Aaron Calvin, was first published on News & Citizen on December 11, 2025, and captures Gailmor's unique journey and impact on Vermont's music scene.
Gailmor's philosophy of life, as expressed in the song, was one of embracing life's pleasures and accepting its end. This sentiment was evident in his April 2020 video, where he sang the same song during the peak of the Covid-19 pandemic. Gailmor's lockdown project, which began with an original song about the virus on March 25, 2020, and ended with Steve Winwood's 'Back in the High Life Again' on May 9, 2021, showcased his resilience and creativity. He even appended a note to the video, stating, 'My philosophy of life since August 5, 1948.'
Born in Manhattan and raised in Philadelphia, Gailmor's early life was shaped by the turbulent post-war era. His father, William, a former Orthodox rabbi, left the synagogue to become a leftist journalist and speechwriter for Henry Wallace, a key figure in Gailmor's early years. Gailmor's own political views became increasingly pessimistic as the 1960s turned into the 1970s, leading him to settle in Vermont, where he found a new purpose.
Vermont embraced Gailmor, allowing his career as a children's entertainer, teacher, and troubadour to flourish. He performed with the Vermont Symphony Orchestra and even opened for Pete Seeger and Arlo Guthrie, earning the nickname 'Vermont's John Denver.' Gailmor's songwriting approach, influenced by the populist folk music tradition, focused on honesty and genuine feelings, as he wrote in his 2006 essay, 'honest writing unearths threads that connect us all, and that songs that were remembered came 'from the gut.''
Gailmor's dedication to community was evident in his role as town moderator in Elmore, where he facilitated Town Meeting Day for decades. He also wrote a song about the event, 'A Town Meeting Tune,' from his 1994 album 'Checking In,' celebrating the annual enactment of small-scale democracy. Gailmor's love for Vermont and its people was a driving force behind his music and community involvement.
Despite his success, Gailmor remained grounded, focusing on his family, including his wife, Cathy Murphy, who died in 2022. He continued to perform, teach, and contribute to the community, leaving a lasting impact on Vermont's music scene and political life. Gailmor's legacy is a testament to his passion, creativity, and deep connection to Vermont, as he sang about leaving this world with a smile, fulfilled and content.
