Obituary of James (Jimmy) Phillips

Jim Phillips

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

Jimmy was a long-time member of The Old 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 twenty-five 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 Gt 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 thirty-eight years, a son, James and his wife Sherri, two granddaughters, Kiara and Kaylynn from Chandler, Arizona, sisters Nanci Race and her husband Robert of Sheffield and Margaret Hawkins of Bloomfield, CT, brothers Leslie and his wife Rene of Atlanta Georgia, Steven and Adam of Sheffield, Michael and his wife Mary of Maine, and Timothy of CT. 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 pre-deceased last year by his sister Barbara Phillips of Springfield, MA.

Calling hours are 10 AM-12 Noon Monday, February 5th with a service to follow immediately from 12 PM-1 PM at the BIRCHES-ROY FUNERAL HOME 33 South Street Great Barrington MA 01230. Condolences may be made through

10 Responses to Obituary of James (Jimmy) Phillips

  1. My sincere condolences and especially to Adam and Timothy, my prayers are with you.

  2. Rest peacefully my friend… You may not be here physically but i know your spirit will be.. Thanks for so many wonderful memories and laughs.. Rock on Toots! You will be deeply missed and always loved.
    My deepest sympathy to your family.🕊🎸❤️

  3. We have lost a very talented man who will be missed by all who knew him.God had plans for Jim and as we all know we are all visitors. My deepest sympathy to all his family.

  4. Holding you close in our prayers during your time of sorrow.
    Extending our deepest sympathies and prayerful assurances.
    GODS peace to you now.
    May Jimmy’s spirit find as much joy in it’s journey as he found in life
    GOD rest your soul my friend Jimmy.

    Nancy and Bill Crawford

  5. Rest in peace Jimmy. Your friends were many. Your music was the best. I was blessed to know you. You are missed but not forgotten.

  6. RIP Jimmy . You will be remembered by so many ,you were one of the kindest people on this earth ! I don’t think I ever saw you without a smile. I’m sure Dave was there to meet you and you are playing up a storm.
    To Jimmy’s family and friends ,Our deepest sympathy .God Bless !
    Tom & Kathy McClurg
    Hillsdale ,NY

  7. My condolences to his family and a life long memory of his contagious smile. God Bless!

    Rose Cronk
    Ashley Falls MA

  8. My condolences to his family and life long memory of his contagious smile.
    God Bless!

    Rose Cronk
    Ashley Falls MA

  9. Faith and Family: Our deepest sympathy on the loss of Jimmy. Our thoughts and prayers are with you. Our community has lost a very talented member. He will be greatly missed by all who knew him God’s peace be with you’

  10. Faith and family,
    I was very sad to learn about Mommy’s passing. My prayers are with you all.
    Chi and Cheryl Ciolina

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