While The Naples Players were staging their first production in 1953, Peg & Charlie Pleasance were at a community theater in Cleveland on their very first date. Charlie saw Peg at a raucous party and immediately offered to drive her home. She turned him down, but before leaving, Peg accepted Charlie’s invitation to see Mister Roberts.

“But Mister Roberts was sold out,” longtime friend Becky Troop recalls. “So they ended up seeing Arsenic and Old Lace. Charlie had to get tickets to Mister Roberts for Peg to go out with him a second time. And they were married within the year.”

Peg operated IBM equipment at Standard Oil and Charlie pursued electrical engineering by revolutionizing telephone technology with a superior answering number identifier system. The couple had three daughters, Barbara, Penny, and Mary Jane, and encouraged them to appreciate the arts.

A trip to the theater is one of daughter Penny’s most treasured memories. “I wanted to see One Flew Over the Cuckoo’s Nest—but it was a freezing Chicago winter night,” she remembered. “Despite the cold, he took me anyway, because that’s the kind of father he was.”

Daughter Barbara remembers her father’s affinity for French culture. “He was an avid Francophile. He loved French food, music, and literature,” she said.

Their mother Peg loved to host parties and entertain guests. “She loved history, especially reading about Henry VIII and Franklin D. Roosevelt,” Barbara said.

Peg & Charlie brought their love for theater, technology, and the humanities to The Naples Players when they retired to Southwest Florida in 1987. Starting out at the Kon Tiki Theater, Peg worked as an usher while Charlie’s engineering talent led him to the scene shop as a builder.

But when The Naples Players sought a new home at the Sugden Community Theater, Peg & Charlie’s roles expanded. Charlie served on the Players’ Board of Directors and Peg became president of The Naples Players Theatre Guild—the theatre’s fundraising committee.

Some of their most notable work came in 2000 at the “Shakespeare Loves Naples” gala—a fundraiser that took nearly a year to organize—as organizers and participants. The interactive event had attendees pleading with queen Peg for salt and good fortune from court jester Charlie.

“Peg & Charlie were examples of kindness and good cheer,” friend Becky Troop said. “Because of that, their decades of leadership, and thousands of volunteer hours, the membership awarded them our highest honor, the Life Member Award.”

“They loved the theater,” daughter Penny said. “We had a Naples Players poster framed. When my parents moved to skilled nursing, we brought it with us and it hung over their bed. It meant the world to them.”

Peg & Charlie put The Naples Players into their estate plans. As members of the theater’s Legacy Society, Peg & Charlie realized the impact legacy giving would have in furthering the Naples Players’ mission. After taking their final bow, Peg & Charlie’s legacy gift offered them one last encore.