Celebrate the life of Jim Freeman, Whidbey Island’s ‘Conductor of Fun’

Published 1:30 am Thursday, June 15, 2023

Jim Freeman stands inside the 1928 Milwaukee Road railroad car, moved to the island by ferry from Kirkland in 1979, on Apr. 20, 2016 in Freeland. “I’ve got 625 square feet, counting everything,” he said. Freeman, 74, known as the Conductor of Fun, died June 19, 2022. (Andy Bronson / The Herald)
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Jim Freeman stands inside the 1928 Milwaukee Road railroad car, moved to the island by ferry from Kirkland in 1979, on Apr. 20, 2016 in Freeland. “I’ve got 625 square feet, counting everything,” he said. Freeman, 74, known as the Conductor of Fun, died June 19, 2022. (Andy Bronson / The Herald)
Pedaling his legs as he holds onto hand rails, Whidbey Island celebrity Jim Freeman at his home, a railroad caboose in Freeland, in 2016. Freeman, known as the Conductor of Fun, died June 19, 2022. (Andy Bronson / The Herald)
Jim Freeman, known as the Conductor of Fun, stands inside the 1928 Milwaukee Road railroad car he called home in Freeland in 2016. He died June 19, 2022, at age 74. (Andy Bronson / Herald file)

FREELAND — Jim Freeman celebrated life with wit, charm and humor.

On Saturday, there will be more laughter, but also tears for the Conductor of Fun.

Freeman died last June 19, a week before his 75th birthday.

A public celebration of life is 2 p.m. at South Whidbey Assembly of God, 5373 Maxwelton Road, in Langley.

“The service will feature remembrances of Jim by family and friends,” his brother Lewis Freeman said.

It will be followed by a reception.

After his death, social media blew up in tributes to the man who gave his all to making Whidbey Island a fun and functional place to live and play.

“Our community is a better place because of Jim Freeman,” it says on the South Whidbey Schools Foundation website. The page has photos and videos in honor of “Jim’s comedic genius, community spirit, kindness and generosity.”

Freeman lived in a 1928 red caboose parked in the woods of Freeland. The Loose Caboose, he called it.

After serving in the Marine Corps, he earned a law degree and did lawyer work.

“A college buddy said Willie Nelson’s manager was looking for a fan club president. I said, ‘Hook me up with him.’ That was 1975. I realized I wanted to be in the entertainment business, not the courtroom,” he told The Daily Herald in a 2016 story.

He traded law for Willie.

“I worked with Willie as his PR guy when not many knew him. After smoking pot on top of the White House, he didn’t need me anymore. Bye-bye, Willie. We parted ways and everything was cool,” he said.

Freeman did commercials, improv and acting gigs in Los Angeles, but he yearned for more.

He found it on Whidbey, where he led parades, festivals and fundraisers, wearing mismatched plaid, waving pompoms and lighting up the island with laughter.

Andrea Brown: 425-339-3443; abrown@heraldnet.com; Twitter: @reporterbrown.