Robert Osborne never imagined he’d spend nearly four decades behind a grill, but now, as the longtime owner of the Big Dipper, he can’t imagine doing anything else.
Opened by his father George Osborne in 1954, the Big Dipper remains one of Owensboro’s most beloved roadside staples, offering old-fashioned hamburgers, pigs in a blanket, and ice cream — all served from a modest building along West Parrish Avenue.
“This business helped my dad put five kids through college and buy a farm,” Osborne said in an interview from London, where he was vacationing while his son helped run the restaurant back home. “From day one, it was good.”
Osborne recounted a pivotal summer in 1981 when a storm severely damaged the building just as Parrish Avenue was being widened and a McDonald’s was going up nearby. At the time, he was a junior at the University of Kentucky and home for the summer.
“My dad was close to retiring — he was more interested in farming — but I helped him rebuild the roof, put up a new sign, and people kept driving by asking when we’d reopen,” Osborne said. “That’s when I fell in love with the business.”
He returned to college and later took a job in Denver, but the pull of the Dipper — and a call from his dad saying, “This business is unreal” — brought him home.
It’s been a family effort ever since. Osborne’s wife Terry handles the payroll and bookkeeping, and he still spends time behind the grill, even while looking for ways to modernize without losing the charm.
“You’re always tweaking things — if I can find a way to save my employees one step in a process, I’ve done my job for the day,” he said.
One of the biggest changes in recent years came with the addition of credit card processing, something Osborne resisted for years. That changed when Independence Bank offered to help set up a system with more affordable fees.
“I was shocked how well it’s gone,” he said. “We hear it all the time — people saying they didn’t stop because they didn’t have cash. It’s made a huge difference.”
Though Osborne remains firmly planted at the Dipper, he’s also eyeing the future. He’s acquired additional property around the restaurant and is envisioning updates to the front facade, while trying to preserve the restaurant’s nostalgic feel.
“There’s been some development around us, and we’re thinking about how to adapt,” he said. “But change is tricky — our customers don’t want us changing too much.”
Even after 37 years, Osborne said he’s in no rush to hand over the reins, although he’s begun mentoring a new generation of employees.
“I’ve had people work for me for 20 to 25 years, and we had one lady who worked for the family for nearly 50 years — she came to our Christmas party at 92,” he said. “You can’t buy that kind of dedication.”
When asked if his father ever imagined the Dipper becoming what it is today, Osborne answered simply, “No.” George Osborne only planned to sell soft serve, and even considered a Dairy Queen franchise before deciding to go independent.
“That changed everything,” Osborne said. “He could do it his way — no franchise fees, no rules. Just good food and hard work.”
As for retirement?
“I keep saying I’m going to, but I don’t know if I can,” Osborne said. “I’ve been blessed. This place, the people, it’s still an inspiration.”
