'I think Florida was always his love': Happy little memories of Bob Ross' Florida roots

If you've ever found yourself wolfing down breakfast in a well-worn Orlando Waffle House booth, there's a decent chance you and Bob Ross have dined in the same space.

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The beloved TV show painter was a man of simple pleasures – like fluffy white clouds and waffles.

“He loved waffles and breakfast for dinner. Nine times out of 10, if there are Waffle Houses in Orlando, he’s probably been in them one time or another,” said Joan Kowalski, president of Bob Ross Inc.

Kowalski, whose parents discovered Ross in the late '70s, said the painter's legacy is woven in with Florida landscape. It's where he was born, where he died and where his painting career got its start.

“I think Florida was always his love, where he most liked to live,” Kowalski said.

Channel 9 traced Ross’ story across the Sunshine State from his start as an art instructor to his rise as a permed PBS show host, and to where his memory still lives on today.

From sun to snow to TV screens

In the late 1970s, Annette Kowalski drove more than 800 miles to take a painting class from a man she’d never heard of: Bob Ross.

She didn’t particularly care who taught the class, she just wanted to learn how to paint like her favorite famous painter on PBS – Bill Alexander.

From 1974 to 1982, Alexander used a paint brush on canvas and his thick, German accent to teach public television viewers the magic of landscape oil painting.

Ross was one of a few instructors certified to teach Alexander’s technique, and his Florida classes were the closest ones to Annette Kowalski’s home in Virginia.

Her daughter, Joan Kowalski, said it took less than a week for her mom to realize the magic happening in front of her as Ross taught her class step-by-step how to turn blank canvas into dreamy pastel mountain scenes.

“She and my dad took him to dinner one night and said, ‘We think you should do more with what you’re doing in the classroom because it’s so magnetic and wonderful,’” Kowalski said.

The rest is history.

Ross and the Kowalskis formed Bob Ross Inc. – headquartered today just outside of Washington, D.C. – and pitched a Bob Ross painting show. “The Joy of Painting” was born.

The show would run on PBS for 11 years, showcasing tutorials from Ross on a simple, black set. The last episode aired 25 years ago Friday -– but continues to attract a cult following of viewers online and on Netflix.

“The things that he says still apply today. He was sort of meticulous in that way he was careful to keep everything timeless so it could live on,” Kowalski said. “It was pretty calculated on his part. He thought of it going on for years and years. And he sure did nail it.”

His career as a professional TV show painter was a sharp contrast from his previous career in the U.S. Air Force, but Kowalski said his talents for the two blended together on screen.

The awe-inspiring landscapes he witnessed while stationed in Alaska served as the inspiration of many of his works, and Kowalski said his military discipline showed when it came to filming.

Kowalski said Ross would travel from his home in Orlando to Muncie, Indiana, to film the show, taping an entire 13-episode season in less than a week, averaging three or four episodes a day.

“He was fast and organized and had everything all planned out so he could get back to Orlando,” Kowalski said.

Happy little memories

More than two decades since his death in 1994, Central Florida continues to offer small odes to its famous former resident, the largest of which is in New Smyrna Beach, where artists are learning step by step how to paint like Ross every day.

Tucked inside an unassuming Publix-anchored strip mall, the Bob Ross Art Workshop & Gallery has taught emerging artists to prefect their happy little trees since 1992.

“That’s the heart and the hub of our teacher training,” Kowalski said.

She said the workshop certifies 100 people a year to go off across the country and teach Ross’ ways to the masses – the same way Ross’ got his start teaching the art of Bill Alexander.

After moving back and forth between the New Smyrna Beach area and Orlando, Ross spent his final days in the City Beautiful.

He is buried just outside Orlando at Woodlawn Memorial Park in Gotha. Fans from across the globe make the pilgrimage to the park to pay their respects to the painter.

His headstone features an engraved photo – his legendary permed locks on full display – with a simple inscription: “Bob Ross, television artist.”

Fans are known to leave trinkets -– and even works of art alongside the grassy gravesite. This month, that included a landscape painting of a sunset, two small squirrel statues, an American flag and a Bob Ross bobblehead collectible.

A dozen miles away, another memorial of Ross emerged earlier this year.

His likeness is larger than life and turning heads in traffic.

Stroke by stroke, muralist Jonas Never brought Ross into focus on the Fairbanks Avenue-facing side of Floyd's 99 Barbershop in Winter Park.

The portrait of Ross stands more than 7 feet tall, a wide smile tucked within his burly beard and a paint brush in hand. Around the corner from Ross, Never painted another famous neighbor – former Winter Park resident Fred Rogers.

“You can’t be that mad stuck in crappy traffic if Mister Rogers and Bob Ross are staring at you,” Never said with a laugh as he put the finishing touches on Ross this March.

Sarah Sleeth, the owner of Floyd’s, said she and her staff brainstormed which local famous figures to memorialize on their walls. Fred Rogers was an obvious choice, but the Orlando-area native said she was surprised when someone suggested Ross.

“I didn’t even know he was from here,” she said.

Unlike on the internet, where Ross has emerged as a meme-worthy icon, his Central Florida legacy has stayed somewhat under the radar.

Kowalski said Ross would love to know that new generations are still falling in love with his soft-spoken simplicity.

“He did want to reach outside of the painting world and become a household name; sort of a role model,” Kowalski said. “He wanted to become a personality that people would be drawn to … and I think he would be incredibly pleased that he’s become a part of so many lives.”

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