James “Jimmy” Phillips, 66, of Sheffield, the son of Leslie and Florence (Crosler) Phillips, passed away Tuesday afternoon at Baystate Medical Center in Springfield. Jimmy attended Mount Everett High School in Sheffield, Berkshire Community College, Boston College and the University of Massachusetts. He was employed at Berkshire School in Sheffield for 24 years. Recently, he worked at International Auto Parts in Pittsfield.

Jimmy was a long-time member of the Olde Yankee Street Rods. He was a popular DJ at parties, weddings or just gatherings of friends and family. Jimmy and his close friend Ernie Louison started a band when they were in high school. The Will Sage Band stayed together, with various members coming and going, for over 25 years. Jimmy was usually lead singer and a self-taught strum guitarist. At one time they were the oldest formed band in Berkshire County.

Always civic-minded, Jimmy parked cars at the Great Barrington VFW for events like the Sounds of Summer. He loved to hang out at the VFW with his friends and his brother on many evenings. He had a wonderful voice and loved to sing karaoke. There was little he didn’t know about music.

Jimmy owned a classic 1971 Trans Am and a neon green 1948 British Anglia he named Goliath. He was famous for entering his cars in car shows with his brother Steven. Over the years, Jimmy won many awards with his cars. He was a frequent entrant of shows in the Berkshires and further away in Lake George.

Jimmy came from a very large extended family. He leaves his wife, Faith, of over 38 years; a son James and wife Sherri; two granddaughters: Kiara and Kaylynn from Chandler, Arizona; sisters Nanci Race and husband Robert of Sheffield and Margaret Hawkins of Bloomfield, Connecticut; and brothers Leslie and wife Rene of Atlanta, Georgia, Steven and Adam of Sheffield, Michael and wife Mary of Maine, and Timothy of Connecticut. He also leaves several nieces, nephews, great-nieces and great-nephews, all of whom were very close to “Uncle Jimmy”; and numerous cousins. He was predeceased last year by his sister Barbara Phillips of Springfield.

Calling hours are Monday, Feb. 5, from 10 a.m. to noon with a service to follow immediately from noon to 1 p.m. at the BIRCHES-ROY FUNERAL HOME, 33 South St., Great Barrington, MA 01230. Condolences may be made through birchesroyfuneralservices.com.