The 1999 Jeep Grand Cherokee represents the second generation of Jeep's midsize SUV. All trims come with a four-speed automatic transmission, with either a 4.0-liter inline six producing 195 horsepower or a 4.7-liter V8 producing 235 horsepower. Four-wheel drive is optional, enhancing the SUV's off-road capabilities. The Grand Cherokee's infotainment options were relatively limited for the time, including AM/FM radio and a CD player, but notably, it added side airbags as an option for the first time in this model year. This durable and capable off-road SUV helped solidify Jeep's reputation for making rugged, go-anywhere vehicles.