At age 69, Jim Freeman is just hitting his stride.

The quirky and ever-enthusiastic South Whidbey resident and well-known master-of-ceremonies has been entertaining crowds for most of his life.

He’s done everything from introduce acts and keep energies high at events like the Island County Fair to providing filler jokes for the annual Mutt Strut Parade.

Though he’s pleased with where he is at, Freeman is the constant perfectionist — after every show, he evaluates his performance to figure out what aspects worked and which didn’t.

It’s a passion with roots tracing all the way back to when he was a kid. While all the other kids were playing cowboys and Indians, Freeman was hosting imaginary game shows at home.

He replicated the energy and confidence of his idol master-of-ceremonies and used a wire hanger to replicate a microphone. Years later while holding a real microphone in front of a real audience, he still feels at home.

Susan Knickerbocker said Freeman can set the pace for any event he hosts, whether the energy is high or low, and provides them with what they need to have a good time.

He also doesn’t refrain from calling people out from the audience with playful banter.

“He brings people together,” Knickerbocker said. “You kind of want to be picked on by him, it’s fun. You just want to make fun of yourself more more.”

But Freeman wasn’t always the confident character he is now.”

“I was a shy kid, which is kind of hard to imagine now,” Freeman said.

After asking his mother about a particularly embarassing experience as a seventh-grader when he cried after being called on by the teacher, she urged him to reassert himself, not wait to be called upon and volunteer to read in front of the class.

Through countless trials and errors, both Freeman’s mother and father taught him the importance of words and public speaking. His father constantly threw him into speech contests and debate teams.

“Really, it took me about 30 years where I’m comfortable doing what I do, but I still have nerves in a physical way,” Freeman said.

When he was with his friend David Ossman, a movie director and producer from South Whidbey, he tried to figure out the reason for his anxious tendencies before getting on stage.

“He said, ‘Jim, it just means you care,’” Freeman said. “It took away the ‘I’m not good enough’ — which is what I thought it was. It’s because I want to do a good job.

“I took all this anxiety and pushed it into a performing career and it’s worked out OK.”

While teaching youths performing in the Whidbey Children’s Theater, Freeman enjoys helping illeviate nervousness that often plagues performers before going on stage.

Making people leave an event happier than when they arrived is where Freeman feels most fulfilled.

He’s done just that for nearly three decades at the Island County Fair. Years ago, while at the fair with his girlfriend, he found that there was not a master-of-ceremonies leading the event.

“I went to say, ‘Who’s in charge of this fair?’ ”

He later met one of the event’s organizers and had the opportunity to host the event on one condition: He would perform for free the first time. If his performance was satisfactory, they would pay him the next time.

“Well, I did that for 25 years,” Freeman said. “Like my dad said, ‘You gotta give away a little toothpaste before you can sell the toothpaste.’”

Often wearing clothing to match the event, Freeman is a loose cannon on stage.

He’ll keep energies high by calling out what he sees, as well as commenting on current events happening around the world.

From the bustling scene of a densely packed event, Freeman’s world slows down when he’s at home.

Living in a 1928 Milwaukee Road railroad car, the walls and shelves contain memorabilia, films and posters from the past.

He is captivated by the era of cowboys, though an idol of his from each generation is included in some shape or form.

“It’s not much different then what you would have as a high school kid really,” Freeman said. “My heroes are still my heroes.”

Those who have seen Freeman in action attest to his enthusiasm and genuine nature on stage.

“Jim is an extraordinarily huge talent in a small place,” said Drew Kampion, a friend of Freeman’s. “If there’s anybody in the creative side of Whidbey’s culture that is iconic, it’d be Jim Freeman. He is an icon of talent and inspiration and a man who lives in complete synchronicity of his high moral values.

“In fact, this guy is completely off the wall, slightly crazy and more fun than a barrel of drunken monkeys.”