20: Dodge Dakota Sport Convertible
The Dodge Dakota was a revolutionary little truck. It was the first midsize truck sold and was the first midsize truck with a full-size V8 engine. For the pickup truck buyer who didn’t need a full size, this was a godsend. The Dakota Sport Convertible was a very rare model released during the early ’90s. The truck featured a full convertible top, which at the time was unheard of for a pickup truck.
The truck didn’t sell well for obvious reasons, as most don’t need a convertible pickup. But funny enough, almost 30 years later the Jeep Gladiator used a similar design. It would appear that the world just wasn’t ready for the Dakota Convertible. You can still find these rare little trucks at the auction and various car shows.