Jeep Grand Cherokee Overland
Price: $40,135
Jeep's mid-size SUV is also its all-around off-road champ. It has been 4 Wheel & Off Road magazine's best 4x4 of the year for nine of the last 24 years. This Grand Cherokee debuted in 2004 for the 2005 model year. For the first time, Jeep emphasized on-road performance in equal parts to the brand's cornerstone, off-road prowess.