The first benefit concert took place on President’s Day in 1988 (then referred to as Washington’s Birthday) at the Holiday Inn. Initially, the funds raised were donated to the hospital. After a few years, the organizers decided to redirect the proceeds to the Cortland Youth Bureau, establishing a scholarship fund to help individuals attend BOCES classes.

After some time, a music program at the Youth Bureau lost its funding, prompting the benefit’s organizers to shift their focus toward supporting music education. The proceeds were used for music lessons and the loan of the instruments to the Youth Bureau's music students. The proceeds also helped finance the sound system for the stage in the newly built Youth Center. . From that point on, proceeds were dedicated to sustaining the music program.

IN 1997, Phil Clarke passed away. Recognizing his contributions, Rosie Rosenthal, one of the main organizers and performers, decided to rename the event in his honor. He enlisted Mel Drake as his right-hand man, who helped organize the event for many years. However, after Mel’s wife passed away, Rosie handled most of the organizing alone. Mel later resumed helping, but following his own passing, Rosie continued the event with others stepping in to support.

The benefit was hosted at various venues over the years, including Holiday Inn, Third Rail, The Tavern, Larrabee’s, The Foot of the Hill Pub, The St. Charles Hotel and others. A key contributor was Colleen Kattau, who played nearly every year. Her availability was a deciding factor when scheduling the event.

The event maintained a low-key format, featuring no more than three or four bands per year. Organizers would pass a hat to collect donations, raising anywhere from $500 to $600 most years. The first event was the most successful, as it was held at the Holiday Inn, where the audience was more or less captive, leading to exceptionally high donations.

The COVID-19 pandemic eventually put the benefit on hold, but it is being revived for 2025. Rosie expressed that if someone else had organized it differently, the event might have raised significantly more money. However, he preferred to keep it simple and community-driven.

This cherished tradition now continues as Playing It Forward, a newly renamed event dedicated to celebrating the lives of musicians from the Cortland area who have passed away. Hosted at the Homer Center for the Arts, this year’s event will raise funds to benefit music programs at Cortland, Homer, and St. Mary’s schools ensuring that the next generation of musicians has the support they need.