Ben channeling Bob Ross before he attempts to paint.
(Photo by Straight8)

Un-Happy Little Trees – Skillset’s Ben Tirpak vs. Bob Ross

First off, who doesn’t love Bob Ross? In a world of anger, hate and scumbag politics, his TV shows are a beacon of chill for those who are suffering from high blood pressure and Trump Derangement Syndrome. Bob’s iconic perm-fro (which he actually hated, but he was so broke he couldn’t afford proper haircuts) became his calling card, along with his soothing one-liners and mesmerizing voice. 

Happy Accidents With Bob Ross

One thing is for certain—Mr. Ross never effed up a painting. Nope, they were all just “happy accidents.” Screw up that tree trunk? No problem, he would just make it a rock. Sneeze all over the canvas? Easy day … he would just add some snow and call it a magical winter wonderland. Damn, this guy was good. 

Ben and I have collectively watched over 100 episodes of The Joy of Painting throughout the years, but we never took the leap into putting paint on canvas. Well, that was about to change. We had to find out for ourselves how difficult it is to make a landscape masterpiece in under 30 minutes. We felt the need … for happy trees. 

Ben showing his Bob Ross inspired painting.

Paint By Number

The first step was to figure out which type of landscape we wanted to paint. We needed something on the lower end of the ability spectrum, since Ben and I have the artistic talent of tree sloths. We finally agreed on “Shades of Grey” (Season 2, Episode 4, if you want to follow along)—some clouds, a few mountains, a lake and an old cabin. How hard could it be?

The next step was buying the supplies. When I heard the Bob Ross empire was worth a whopping 15 million dollars, I rolled my eyes in disbelief. But then, after purchasing all the required materials, my skepticism turned to anguish when my final credit card bill read $161.72. The pressure was on to create a work of art that would fetch that dollar amount at the local art walk. The cards were starting to stack against us, but we are always up for a challenge. 

Tv Time

As Ben started following Bob Ross’ step-by-step tutorial, we immediately realized one thing: This wasn’t going to get done in 30 minutes. With the amount of “How in the hell did he do that?” and “For the love of god, would you please rewind?” coming out of our amateur Picasso’s mouth, I could sense we were in for a full day’s work. 

Another obstacle we encountered was the difficulty of the “wet-on-wet” style of painting. Bob might have mastered this process, but for the beginner, it’s a bitch. Just want a clean hillside of snow? Hope you like some mud, sky and whatever other colors that are on your palette mixed in. Getting a single color swipe on your board is nearly impossible and, ultimately, highly frustrating. 

Mastering Mistakes

Another mistake we made was not properly prepping our work area. Adequate ventilation and a floor (and walls) you don’t mind getting dirty are a must. Unfortunately, we didn’t have either. Our studio was soon peppered with paint splatter from beating our brushes against the easel, and, after fifteen minutes of inhaling paint thinner, Ben and I were both high as shit. We were finally starting to see those happy trees ole Bobby was talking about. 

Ben's final product.  We think he did a great job!

Finally, after three and a half hours, our first masterpiece was completed. Sure, it looked like it was painted by a psychopath with methamphetamine-induced spasticity, but it was ours, and we were damn proud. A lot of life lessons were learned this day. Will we continue down our path of oil-based mental therapy? I highly doubt it. But we do have a newfound respect for this PBS superstar. 

5 Quick Facts About “Bust ’Em Up Bobby”

  • He spent more than 20 years in the United States Air Force and achieved the rank of master sergeant. Despite his calm demeanor, rumor has it he was a total hard-ass in the service, earning him the nickname “Bust ’Em Up Bobby.” 
  • Bob actually painted his pictures three times—one prior to taping to be used as an off-screen guide, one during the taping of the show and one after the program to be photographed for his portfolio. 
  • Personal lessons from Bob Ross would cost you $375 an hour.
  • Bob was missing a finger. We were hoping we would find out it was bitten off in a bar fight, but the unfortunate truth is that he lost it in a woodworking accident. 
  • He would film an entire thirteen-episode season in two days, and he completed more than 30,000 paintings in his lifetime. 

He’s not just a part-time painter, Ben’s also the co-host of our podcast Skillset Live!  Get in on the conversation on our social media pages or pick up a back issue at

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