If there’s one thing Kenny Wallace knows how to do, it’s tell a good story. The NASCAR veteran and fan-favorite personality recently had listeners in stitches on his “Herm & Schrader” podcast when he recounted a side-splitting tale about his older brother, Rusty Wallace. The story took a detour down memory lane to a time before Rusty was the NASCAR legend we know today — a time when he was just trying to balance a regular job with his dreams of racing.

Kenny set the stage for this epic story by reminiscing about the days when he and Rusty, alongside NASCAR crew chief Paul Andrews, worked at their Uncle Gary’s janitorial supply business, “Okay Vacuum & Janitorial.” What followed was a story of frustration, determination, and an accidental mishap that turned out to be a blessing in disguise.

The infamous 55-gallon drum mishap for Rusty Wallace

Kenny Wallace kicked off the story by explaining the tough choice Rusty and Paul faced in their early days. Every Friday night, the Wallace brothers would head to the Ozark Empire Fairgrounds in Springfield, Missouri, to race. But here’s the kicker: they still had to punch the clock at Uncle Gary’s business before they could hit the dirt track.

“Every Friday night, we’d run Springfield, Missouri, Ozark Empire Fairgrounds,” Kenny shared with his co-host, Ken Schrader, on the podcast. “Uncle Gary says, ‘You boys need to decide if you’re going to be race car drivers or work here!” This ultimatum came down to a tough decision. Were they going to keep chasing their racing dreams, or stick to their day job? The Wallace brothers were itching to hit the track. As Kenny put it, “They’re like, ‘Oh boy, we have to leave at like 3-3:30 to make it.’ That’s for the first heat.” But Uncle Gary wasn’t about to make it easy on them. In a hilarious twist, he decided to put Rusty to the test one fateful Friday.

As the story goes, Uncle Gary gave Rusty Wallace what seemed like a simple, but time-consuming task: deliver a 55-gallon drum of chemical supplies across state lines to Illinois. The only catch? The clock was ticking, and Rusty had a race to get to. You can almost hear the frustration in Rusty’s voice as Kenny describes the scene. “He hands Rusty this sheet of paper and goes, ‘I need you to deliver this 55-gallon drum of chemical to Illinois,’” Kenny recounted with a chuckle. “Rusty is pissed.” Rusty, eager to get the job done and hit the road, loaded up the box truck — a clunky vehicle with a back held together by chains instead of a roll-down door. Kenny painted a vivid picture of Rusty’s mood: “He’s so mad. He starts gear banging, WOMP WOMP WOMP, goes across all these railroad tracks, backs that baby up. Beep beep beep.”

But as Murphy’s Law would have it, things didn’t go as planned. When Rusty Wallace arrived at his destination, ready to hand over the goods, there was just one problem. The guy waiting for the delivery looked at Rusty and asked, “What 55 gallons?!” The realization hit Rusty like a ton of bricks. “Rusty says, ‘Oh no, I know right where it’s at!’” Kenny laughed, recalling the story. That 55-gallon drum had bounced right out of the truck bed somewhere near the river on his way to Illinois. By the time Rusty made it back to the shop, Uncle Gary had had enough. Rusty’s days at “Okay Vacuum & Janitorial” were over.

Kenny’s conclusion? It was the best thing that could have happened to Rusty. “So Gary fired him. It was the best thing to have happened!” he said, clearly amused by how it all played out. While it may have been a tough blow, Uncle Gary turned out to be a pivotal moment for Rusty Wallace. No longer tethered to the family business, Rusty focused entirely on his passion for racing. And as history shows, that gamble paid off big time.

How Rusty’s carrier panned out

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Rusty Wallace went on to become one of the most successful drivers in NASCAR history, clinching the 1989 Cup Series Championship, earning 55 Cup Series wins, and eventually being inducted into the NASCAR Hall of Fame in 2013. Who knew that losing a job over a spilled drum of chemicals could lead to such a legendary racing career?

Rusty himself has often spoken about the early struggles of making it in the racing world, emphasizing the importance of perseverance and passion. And it’s stories like these, shared by his younger brother Kenny, that offer a glimpse into the gritty, behind-the-scenes moments that shaped NASCAR legends. As Kenny Wallace’s storytelling reminds us, sometimes life’s funniest mishaps lead to the greatest successes.

What followed was an incredibly successful career. Wallace won the Rookie of the Year title in 1984 and never looked back. Concluding a career that spans over 40 years, Rusty Wallace put an ever-lasting mark on the world of NASCAR. His success with Roger Penske‘s team will always be one that remains in the hearts and minds of fans. It even spawned a 16-year streak where Wallace won at least one race every single year.

Eventually, after calling it quits from the grueling life of stock car racing, Rusty Wallace continued ownership of his team. He even fielded his son Steve Wallace in one car. However, RWR shut down at the end of 2013. At the moment, Wallace continues his love for racing as an analyst.