On Friday, March 20, 2020, news that famed singer, Kenny Rogers passed away hit the news outlets. He passed away of natural causes at his home in Georgia. As a fan, I had to find a Youtube video of him singing, The Gambler, to refresh my memories again. As a writer for an automotive website, I also had to stop and wonder what kind of cars Kenny Rogers owned, or if he was even an auto enthusiast at all.

After a little research, I was able to narrow down some information from his life that involved his car-related interests. I hope you enjoy this little recap of those interests. Some of the information I found was enlightening, even to me. 

1956 Ford Fairlane

The first vehicle Kenny Rogers bought was a 1956 Ford Fairlane. As it turns out, he was a part-owner. His dad was the one purchasing the car but came up short on funds. So, Kenny offered to help with the part-time job he had at the time. His dad agreed, and they split up the driving schedule. Unfortunately for Kenny, his dad scheduled all of Kenny’s time while he was also supposed to be in school. 

1959 Chevy

Since the first purchase didn’t go as expected for him, Kenny bought his second vehicle on his own. It was a 1959 Chevy. He used it to get from one musical performance to another until it got repossessed.

Cadillac

He still managed to get from gig to gig and eventually worked his way up to a Cadillac. In an interview from 2013 with Yvonne Marton of wheels.ca, Rogers explains that he thought the Cadillac brand carried enough influence with music and venue managers that they would pay him more for the gigs. So, he purchased them thinking Cadillacs mean success. People pay more for success, or at least for the air of success. 

Harley Davidson

Harley Davidson motorcycles were also an interest of his. He loved them. However, In an interview with cmt.com in 2004, Rogers explained that he had an awakening experience when riding one that turned him off of motorcycles as a whole. He explained that he enjoyed the motorcycles but realized that his enjoyment of speed and lack of maintenance was going to get him in trouble. The day after the realization, he got rid of it.

Racing In Movies

Racing was also an interest of Rogers. In 1982 he was in Six Pack, a comedy-drama about a race car driver named Brewster Baker having to work with orphans on his pit crew. Rogers was the lead in the movie, as he expanded his skills from singing to acting as well.

Racing Chassis

Not all of his interest in racing had to do with the movie, though. He also became a sponsor of Sprint car team through the 1980s and 1990s. Eventually, his enjoyment of the sport would lead him to establish a company called The Gambler Chassis Company. It produced a chassis aptly named, “The Gambler”, after his hit song. That chassis and its variants would go on to perform well in the United States and Australia. 

Varied Tastes In Cars

Kenny Rogers would go on to own many vehicles in his lifetime. As it turns out, he did become a little bit of an auto enthusiast. His tastes varied from a 1980 Stutz IV Porte, an Excalibur, a Delorean, a Bentley, to a Rolls Royce would be all be among his collection. But, he said as he got older, he began caring less about how people viewed him.

“I drive a Lexus sedan, because stature to me is not dictated by the car you drive, anymore. At one time, I thought it was. I think you get into that rut.”

Kenny Rogers was 81. Rest In Peace.