27: Dodge Ram 1500
In the last decade, the Dodge Ram has become one of the best-selling pickup trucks of all time. Part of that is because the truck has a timeless design and many standard features for the price (via Autolist).
But older versions of this truck are problematic and expensive to repair. The transmission is the most common failure in the Dodge Ram pickup. This repair will generally set you back around $2400 for a full replacement.