Trim: GLS four-door
Original MSRP: $16,910
KBB private party value: $6,200
Retained value 36.7% The Wrangler hasn't changed a whole lot during its existence, but the 2003 is a particularly sweet prize for lacking the square headlights that plagued Wranglers during the '80s but pre-dating the stretched-out "unlimited" Wranglers that came later that decade. Still, 2003 was a year of big changes for the Wrangler, which came in its high-end Rubicon form for the first time. The soft and hard tops fit differently, the metal side mirrors were swapped out for plastic, the audio sound bar along the roll bar was replaced with smaller sound pods, the seats looked and felt different and the transmission switched from a three-speed automatic to a four-speed automatic with overdrive that could be activated and deactivated with the flip of a switch. The biggest change in the base model, though, was the 2.4-liter Power Tech engine that replaced the old 2.5-liter version with the Jeep since its days at American Motors. It still has the boxy look, the 4x4 capability and off-road chops of its predecessors, though, which is all most fans look for and the biggest reason they still pay big money for it today.