Robert “Bob” Cunningham

WINSLOW – Robert “Bob” Cunningham, 89, joined his high school sweetheart, Sylvia, in death on May 13, 2026, after a brief illness.

Bob was born on Feb. 20, 1937, to Robert F. Cunningham Sr. and Merease M (Albert) Cunningham and lived most of his life in Winslow.

Bob was best known for his nearly 60 years of barbering at his shop on Clinton Ave. He joined the Navy right after graduating from high school in 1955. He served on the Navy destroyer USS Gatling, where he started his barbering career. When Bob was home on leave, he contacted the widow of a Waterville barber and purchased her husband’s equipment for $25. And opened his shop in 1964. Haircuts for children were 75-cents and adults were $1. Later on, he expanded his business by also becoming a hairdresser and serving on the State boards, traveling and giving exams to cosmetology students.

It’s been said that Bob never knew a stranger. He knew all his customers and their families and extended families and their life histories. Bob loved to work. As a kid he mowed lawns and shoveled snow for 25-cents. He delivered newspapers, He started sweeping floors at Dexter’s Drug Store and worked there throughout his high school years. He often spoke fondly of Mr. Dexter who became like a second father to him. Some of the other jobs Bob had included selling real estate and delivery driver for Nissen’s Bakery.

Bob’s friends and family knew him as a “picker’. He loved buying and selling secondhand treasures, often buying out local yard sales at the end of the sale. Bobby knew how to stretch a dollar. He made sure to pass this skill on to his grandchildren. It’s not surprising that each great grandchild received a piggy bank from their beloved Pepre’ along with a $5 bill and Instructions to save.

Bob and Sylvia enjoyed many summers with their daughters at their camp on China Lake. After retirement, Bob could be found visiting with his friends at Fortin’s Furniture and Kim’s Garage. He enjoyed bringing them snacks while chatting and reading their newspapers.

Bob will be sadly missed by his daughter, Lisa Landry, his son-in-law, Gary Violette, his grandson, Kaleb Violette (DeEtte), granddaughter, Kristi Violette (partner, Todd) and five great grandchildren, many cousins, and dear friend Jason Fitch and his wife, Love.

He was predeceased by his loving wife of 65 years, Sylvia (Loubier) Cunningham, a daughter, Lynne (Cunningham)Violette, son-in-law, Russell Landry and grandsons, Joshua Violette and Levi Violette.

Per Bob’s wishes, there will be no funeral. Special thanks to the kind people who cared for him at Togus VA Medical Center Hospice.

Arrangements are under the direction and care of Gallant Funeral Home, 10 Elm Street, Waterville. An online guestbook may be signed; condolences and memories shared at http://www.gallantfh.com.

In lieu of flowers, donations may be made to: Winslow Community Cupboard, C/O Kristi Letourneau, 26 Lithgow St., Winslow, ME. 04901.