The Creative Journey of Renowned Artist Herman Cherry

Having recently been inducted into the Hamptons Fine Art Fair’s ‘Hall of Fame’ this past July, we’re reminded not only of the of Herman Cherry’s influence on the art world at large, but more specifically his importance to the cultural fabric of the East End. From contributions to the Federal Art Project via the WPA in the 1930s, to chairing National Arts Conferences in Woodstock, NY in the late 1940s, fundraising for and participation in CORE in the 1960s, and political fundraising projects for the McGovern campaign in 1972, Herman’s charitable nature and high moral fiber are remembered fondly by all who knew him.  

Most notably to some, Cherry was a prominent player of the Artists & Writers Softball Game. Having been a veteran of the first game, Cherry’s involvement is a testament to his dedication to both the arts and community in East Hampton.

This beloved Hamptons tradition dating back over 70 years, brings together creative minds for a day of friendly competition and philanthropy. The game has always served as a fundraiser for local charities, supporting causes that are close to the hearts of participating members of the community.

Cherry’s role in the Artists & Writers game extends beyond having only been a player. He had been instrumental in organizing and promoting the event, ensuring its success year after year. His enthusiasm and commitment, and the inspirations it’s given others is what’s made it a cornerstone of the East Hampton summer calendar.

In “Hamptons Bohemia: Two Centuries of Artists and Writers on the Beach”, Helen Harrison and Constance Ayers Denne recount one of the most memorable moments of Cherry’s involvement in the game as when he pitched the last painted grapefruit to George Plimpton in 1972. According to sources, Plimpton, a very prim and proper man, was rather displeased at being covered in juice and pulp after making contact with the phony ball. The idea of the painted grapefruit had been conceived by Louis Schanker, Willem de Kooning, and Franz Kline as a way to get back at Philip Pavia who “took the game seriously – far too seriously”. This was the final appearance of the grapefruit, which had become emblematic of the game’s humorous and spontaneous spirit.

As East Hampton continues to celebrate its artistic and literary heritage, Herman Cherry stands out as a pivotal, yet unsung, figure whose legacy will be remembered for years to come. His work and community involvement, along with of all the other past and present players of the Artists & Writers Softball Game, have left indelible marks on the East End, embodying the spirit of creativity and philanthropy.