31: 1993 Jeep Grand Wagoneer – $16,500
The Grand Wagoneer was for a long time one of the only family-friendly SUVs that you could get. When the ’90s rolled around, the platform was quite dated and it was time for a redesign. The final product was the Grand Cherokee, but for a year, there was a Grand Cherokee with the Grand Wagoneer name on it (via Trinity Auto).
The finished product was a handsome vehicle to look at that was capable of off-road. But there is no way that a Jeep product from this era should justify the high price tags drivers are currently seeing. The Wagoneer continues to rise in price, and there is no method to the madness.