The Jeep Grand Cherokee made its debut in 1991. The models available were the entry level, Laredo and the Limited. All Grand Cherokees were equipped with airbags on the side for the driver and anti-lock brakes on all tires. A 4.0-Liter engine with six cylinders and 190 Horsepower powered the Grand Cherokee. Later that year a 5.2-Liter V8 engine with 200 horsepower was introduced for the Grand Wagoneer, which was a version of the Grand Cherokee. Unfortunately that model lasted just one year. In 1994, the entry level model was renamed the SE and all Grand Cherokee models with an automatic gear system had a V8 engine. In 1995, the Grand Cherokee was only available in SE and Limited versions. The vehicle got disc brakes for all the tires. In 1996, side airbags for the passengers were added. In addition, buttons for the music system and horn were added on the steering wheel. In 1998, a 5.9 version of the Limited was introduced.

In 1999, the second generation Jeep Grand Cherokee made its debut. The new vehicle was longer and taller than the 1998 Jeep Grand Cherokee. The entry-level engine was a six cylinder 195 Horsepower 4.0 Liter engine, while the other engines were a 4.7-liter V8 with 230 horsepower. Both the engines came with an automatic transmission or four-gear manual transmission. The Jeep Grand Cherokee had the option of three-wheel or four-wheel drive. The Selec-Trac could change from two-wheel drive to four-wheel drive, while the Quadra-Trac would always be on four-wheel drive. The Quadra-Drive could direct all the engines power to any one tire at any moment. In 2000, all the two- wheel drive vehicles were replaced with a V8 engine, and the Selec-Trac four-wheel drive became available with a V8. In 2001, an additional gear was added to the Grand Cherokee Model with the V8 engine. The Limited came with 17-inch tires, while the other models came with a garage door opener system that operated with any garage. Two new models were introduced in 2002; the Port which was equipped with leather seats, heated mirrors and the special edition which had a CD player that could store 10 CDs at a time. Also introduced was the Overland model that was powered by a 260-horse power V8 engine. In 2003, the Laredo came with improved front seats.

The third generation of the Jeep Grand Cherokee was launched in 2005. The new model was longer and taller than the 2004 model. The new vehicle came in Laredo and Limited models that seated five passengers. The Laredo had a 3.7-Liter V6 engine while the Limited had a 5.7 Liter Hemi V8. All Grand Cherokee models were now equipped with anti-lock brakes, 17-inch tires, a system to assist the vehicle from skidding, and a warning system while the driver is in reverse to warn of any obstacles. In 2006, the Overland and SRT8 models were added to the lineup.