Jim Freeman stands inside the 1928 Milwaukee Road railroad car, moved to the island by ferry from Kirkland in 1979. He’s got 625 square feet of living space.

Meet Jim Freeman, Whidbey’s Conductor of Fun

WHIDBEY ISLAND — A portrait of Roy Rogers lords over the bed.

A plastic Disney cartoon party banner serves as the bathroom door.

Twinkling holiday lights stream across the ceiling.

On a small TV, a music video with Marvin Gaye crooning “How Sweet It Is” echoes through the metal chambers of the caboose.

What’s up with that?

This red train car parked in the woods of Freeland is the home of Jim Freeman, 68, who calls himself the Conductor of Fun. He pretty much lives up to the name in his Loose Caboose.

“It’s the only caboose on Whidbey that has a guy living in it,” Freeman said. “It’s a man-caboose.”

Tall and lean, with long wispy gray hair, white tennis shoes and a flip phone, he’s one of those characters you’d expect to find on Whidbey Island. Think Jim Varney, the comedian best known for his role as the rubber-faced Ernest P. Worrell.

Freeman’s voice resonates with confidence and quirk. His mannerisms ooze charm. No wonder he’s the perennial emcee at poetry slams, festivals and fundraisers. He cranks out a witty column for the Whidbey Weekly. Mukilteo Coffee Roasters named a coffee blend after him.

“He’s an original, a total original on this island,” said retired teacher Jean Shaw, his co-host for fundraisers. “We’ve done all these talent shows together. We had the school board dress up in black garage bags and go down the aisle doing ‘The Grapevine.’ They weren’t just talent shows.”

Freeman hails from L.A. No surprise there.

He moved to Whidbey 33 years ago, and a year later settled into the caboose that’s 10 feet wide and 36 feet long.

“It’s probably like living in a motorhome,” he said.

The 1928 Milwaukee Road railroad car was moved to the island by ferry from Kirkland in 1979. The previous owner added a kitchen nook. That’s where Freeman keeps his frozen White Castle cheeseburgers, Darigold chocolate milk and Gates Extra Hot Bar-B-Q sauce, shipped from Kansas City.

Freeman added on an office nook.

“I’ve got 625 square feet, counting everything,” he said.

Space enough for such creature comforts as an arcade pinball machine that works, no nickels needed.

“There’s electricity and a wood stove,” Freeman said. “It’s either too hot or too cold. There’s no insulation.”

When it rains, it pours noise.

“When the wind hits right, it’s like you’re on the road,” he said.

“When I had my basset hound here, when he would walk inside the perfect movement of his legs would get it to vibrate.”

Dearly departed dog Norton is now buried in the 6-acre yard. That’s one reason why Freeman isn’t going anywhere and, hopefully, neither is the Loose Caboose.

It’s held in place by a little piece of metal lodged under the wheels.

“It ain’t going anywhere,” he said. “If it ends up on Newman Road there’s 44,000 pounds of steel that’s going to be blocking the road.”

The caboose is hidden in the trees, but people find him anyway.

“There’s only two of these (cabooses) ever made and I got one of them,” Freeman said. “One day I hear a car come up the driveway. The guy gets out and he starts taking pictures. He said, ‘I’ve been looking for this train for 20 years. I’m writing a book.’ The guy was an FBI agent and his hobby was trains. I had no idea this was that important.”

How Freeman ended up here is a long story. Here’s the condensed version:

“I got out of the Marine Corps, went to law school, got a job traveling with a law fraternity. When I started practicing I realized this is not fun, there’s no happiness, there’s not a lot of honesty,” he said.

There were some memorable moments: “I once had lunch with Judge John Sirica during the Watergate trial,” he said.

Still, he craved excitement.

“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 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 got the show biz bug.

“I started doing TV commercials, and I had an ad running up here in Seattle for a bartending academy in Renton. I was the guy who’d throw all the stuff off the desk, saying, ‘You want to be your own boss? Want to have your own hours?’”

Freeman also did radio, improv and got bit parts in films, but he yearned for more.

“I was in L.A. at a bar on a Friday wondering, what am I going to do with my life? A guy was staring at me. I said, ‘Want to buy me a drink, want to kiss me, what’s the big deal here?’ He said, ‘I’ve seen you somewhere … You’re the bartending guy!’ He said he was from Seattle. I said, ‘If I could live anywhere in the area but not in Seattle, where would you go?’ He said ‘Whidbey Island.’”

Freeman moved to a Whidbey beach house in 1983 and commuted to L.A. for gigs. A year later, the caboose became available.

He gradually weaned himself from California and settled into island life full time.

“It was divinely ordained, this entire program,” he said.

Sorry, ladies. He’s taken.

He and his girlfriend have been dating for decades.

It’s another long Freeman tale.

“We are not married officially, although we did get married once in L.A., at a carnival, for only a dollar,” he said.

Over the years he divided his time between an island farmhouse they rented and his caboose. Now she’s in Vegas helping out with her first grandchild and he’s sleeping under the watchful eye of Roy Rogers.

The Conductor of Fun plans to keep it as his man-caboose until it’s time for him to go the train crossing in the sky. Not anytime soon, though.

“My grandpa told me. ‘Don’t ever quit working, Jimmy. It will kill you,’” he said.

“I’ve got two poetry slams and a jazz festival next week, a video to shoot. I feel like I’m still moving in, 33 years later.”

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

Jim Freeman points to the original color of his caboose.

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