Dana Jester: Artist, Teacher, and a Living Link to Bob Ross
- Hope Blakely
- Oct 1
- 3 min read
I still remember the first time my phone lit up with “Dana Jester.” I was sitting in a movie theater a few weeks before my first workshop with Dana and Steve. I stepped into the hallway, heart racing… and in seconds Dana’s easy laugh and friendly “Hey, what’s up?” made it feel like chatting with an old friend. That’s Dana—approachable, funny, and genuinely kind.
From Red Key to Old Town Arvada
Born in Red Key, Indiana in 1954, Dana later made a home in Arvada, Colorado (2000–2009). Many locals still remember his Jester Art Gallery on Grandview in Old Town (open from around 2001–2004), right across from where the train station now stands. For our community, his presence stitched Arvada into the larger Bob-Ross-family story—one I’m honored to continue today in my own gallery.
A Life Intertwined with Bob Ross
Dana first met Bob Ross around 1982 in Muncie, Indiana, and soon appeared on The Joy of Painting. More than a guest, though, Dana became a close friend—fishing, traveling, and sharing countless behind-the-scenes moments with Bob and Steve.
He even stood beside Bob in New York City’s Times Square (1998) when Bob led a massive outdoor painting event. To this day, Dana keeps Bob’s memory alive by sharing stories, photos, and behind-the-scenes glimpses on social media.
Beyond Landscapes: Dana’s Expansive Skillset
Like Bob, Dana mastered the Bill Alexander wet-on-wet landscape tradition. But he went far beyond it:
Portraits (notably Native American subjects) with remarkable depth and respect
Wildlife paintings where you can feel each whisker or feather
Landscapes filled with atmosphere and mood
Acrylics and oils, both handled with mastery
This breadth is why collectors should take note: Dana knows when to add detail, when to let the canvas breathe, and how to put heart into every stroke.
“Yellow Mountain” in My Collection
The first piece I ever brought home from Dana was Yellow Mountain (purchased in 2019). It’s beautiful on its own, but what makes it priceless are the memories attached: early workshops, friendships, and the beginning of a long, joyful chapter learning from Dana and Steve.
Workshops, Friendship & Community
Since that first class in 2019, I’ve had the joy of learning from Dana and Steve many times. Dana brings more than technique to a room—he brings humor, encouragement, and a cool-uncle wisdom that makes everyone feel welcome. Through those workshops, I’ve met friends who now travel, paint, and grow together.
Glenna Pittman: The Heart Behind the Scenes
If Dana is the spark, Glenna Pittman is the steady glow. She handles registrations, emails, morning coffee, and a hundred unseen details that make every event smooth. She’s not a painter (though she once let us film her dabbling with a brush!), but her warmth and laughter are part of what makes every workshop unforgettable.
For Collectors: Why Dana Matters
Owning a Dana Jester painting means more than acquiring art. It means holding a piece of living history:
Skill + Soul: precision where it matters, restraint where it elevates mood
Versatility: from portraits and wildlife to classic mountain scapes
Legacy: a living, breathing connection to Bob Ross, carried forward in Dana’s own artistry
Where to find him now: The best way to follow Dana and see his available works is through his Instagram: @_jesterart.
📺 Dana Jester on The Joy of Painting
For those who’d like to see Dana in action with Bob Ross, here are the episodes he painted:
Season 5, Episode 3 – Mountain Blossom
Season 17, Episode 13 – Mountain Beauty
Season 27, Episode 10 – Sunlight in the Shadows
Note: These episodes were once available on YouTube, but Bob Ross Inc. has since removed them. Even if they’re harder to find now, the impact—and Dana’s artistry—remain an important part of the show’s history.
✨ Dana Jester is more than an artist. He’s a teacher, a friend, and a bridge between generations of painters. From Old Town Arvada to classrooms across the country, his art and his spirit continue to inspire—and collectors who know, know.
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