The Jeep Cherokee was Jeep’s bread-and-butter SUV for decades, running between 1974 and 2023. The vehicle started off as a body-on-frame design, and transitioned into a unibody type with the introduction of the second generation in 1984. This particular 1999 Jeep Cherokee is a fine second-generation variant that’s undergone an extensive built to turn it into what you see here. As if a standard Cherokee wasn’t potent enough, this one’s got everything turned up to eleven. It comes with just 500 miles since the build and the owner reportedly has receipts too.
Wearing a straight shade of gray, this 1999 Jeep Cherokee’s radical appearance is the result of the mods that it wears. You’ve got a set of Dirty Life beadlock 17-inch wheels with Hercules TSI off-road tires. Then, there’s a roof rack with a built-in LED light bar. Moving on, we spot a front bumper with a 9500 synthetic rope winch, a Rock Hard 4x4 rear bumper with tire and extra gas can carrier, Rusty’s side panels, Rock Cover steel fender flares, and 5x7 LED headlamps. Meanwhile, the whole thing benefits from a Rusty’s Off-Road 6.5” long travel 3-link lift kit. There’s also a set of LED rock lights for added visibility when you’re deep in the trails and it’s becoming dark. There’s even a complete powder-coated roll cage for added safety. The interior of this 1999 Jeep Cherokee is reportedly new, and includes Corbeau bucket seats, as well as a touchscreen infotainment system with Bluetooth. Naturally, you’ve got all the conveniences that a standard second-gen Cherokee came with, including cup holders, storage compartments, air conditioning, map lights, and more. You’ve also got plenty of trunk space, even with the presence of two amplifiers and speakers back there.
Bearing a new 350ci V8, this 1999 Jeep Cherokee is ready to rumble at your beck and call. It’s got a rebuilt automatic transmission sending power to the rear wheels, with on-demand four-wheel drive. There’s an upgraded 9-inch Electrical Max Performance cooling fan, front and rear lockers with a 4.56 gear ratio and Currie differentials, a Tom Woods 1310 series CV driveshaft, and more.
1999 Jeep Cherokee Sport
5.7L V8
Automatic Transmission
RWD w/ 4x4
Gray Exterior
Gray Interior
New 5.7L V8 Engine
Rebuilt Automatic Transmission
Aluminum Radiator
Upgraded 9” Electrical Max Performance Cooling Fan
Complete Powder Coated Roll Cage
Rock Hard 4x4 Rear Bumper with Tire & Extra Gas Tank Carrier
Rusty’s Off Road 6.5” Long Travel 3 Link lift kit
Rusty’s Side Panels
Rock Cover Steel Fender Flares
Tom Woods 1310 Series CV Driveshaft Front and Rear Elocker
4.56 Gear Ratio
Currie Differentials, Front Bummer with 9500 Synthetic Rope
Winch 5x7 LED Headlights
LED Rock Light Kit Roof Rack with LED
Built in Light Bar
Dirty Life Bead Lock 17” Wheels
35x12.50R17 Hercules TSI Off-Road Tires
Front & Rear Elocker
4.56 Gear Ratio
New Interior
Corbeau Front Bucket seats
New Bluetooth Sound System
LED Touch Screen Console
Custom Paint Job
Receipts Available Reported by Current Owner
500 Miles on Build
The Jeep Cherokee was Jeep’s bread-and-butter SUV for decades, running between 1974 and 2023. The vehicle started off as a body-on-frame design, and transitioned into a unibody type with the introduction of the second generation in 1984. This particular 1999 Jeep Cherokee is a fine second-generation variant that’s undergone an extensive built to turn it into what you see here. As if a standard Cherokee wasn’t potent enough, this one’s got everything turned up to eleven. It comes with just 500 miles since the build and the owner reportedly has receipts too.
The Jeep Cherokee turns 50 and in that time, each generation has satisfied the wants and needs of their custodians. Present today is a lovely example of what is the Jeep Cherokee’s most popular model and takes shape with this 1999 Jeep Cherokee Sport. This 90s icon features a complete restoration and has reportedly run 1000 miles since its glow up.
The Jeep Cherokee is an epic line-up of SUVs from Jeep. The latest generation bowed out this year amidst some calls over the use of the Cherokee nameplate. Controversy aside, the Cherokee started life as a full-sizer, moving into the compact category with the second generation, where it has remained ever since. This 2001 Jeep Cherokee XJ Sport comes from the second generation, known as the XJ. The XJ ran from 1984 to 2002 and was produced outside the United States as well. Up for grabs is a nice 2001 Jeep Cherokee XJ Sport with just 59,633 reportedly original miles.
The Jeep CJ or Civilian Jeep was born out of a corporate need to survive. Willys-Overland used to supply the US Military with Jeeps for World War II. In 1944, they realized that with the War due to end, their lucrative orders would also dry up. So, they turned their attention to an America that was soon due to experience an agricultural and industrial boom, and decided to adapt the military Jeep into the CJ. This proved tougher said than done, because military Jeeps had lifespans of months or even weeks. They were throw-away items. A civilian Jeep, on the other hand, would also experience harsh use but be expected to last for years and even decades. Nevertheless, they did it, and the Jeep CJ was made from 1945 until 1986 across several iterations. Then, the successor gained a name that we know to this day; Wrangler. So, why not celebrate that glorious legacy and buy this 1978 Jeep CJ-5 that’s up for sale in Florida? With a 258ci straight six, a custom paint job, Bilstein performance shocks and more goodies, this is an off-road buddy that will never let you down.
A fun-loving off-roader for those who truly enjoy exploring the great outdoors, Jeep’s Wrangler can directly trace its lineage to the Jeep CJ line-up from 1948 onwards. In fact, it’s not hard to see the family resemblance between the Jeep CJ and the latest JL-Series Wrangler. Case in point, we have a nicely modified 2018 Jeep Wrangler Unlimited Sport for sale from Slidell, Louisiana for sale today. With a mere 55,850 miles, this four-wheel drive off-road beast could be yours if you desire a machine that can keep up with your thirst to explore the unexplored, the desire to traverse the wilderness, the will to create new paths.
The Civilian Jeep, or Willys Jeep CJ is what eventually became the Wrangler that we know and love to this day. Conceived in 1948 as a civilian variant to the popular military Jeep, the CJ ran until 1986. The CJ-7 variant was one of the latest at the time, made between 1976 and 1986. That’s what we have here today, a 1985 Jeep CJ-7 for sale from Burnsville, Minnesota. This Jeep packs around 91,747 miles on the clock and has received a 327ci V8 engine upgrade, with a Holley 4-barrel carburetor. It’s also got the Heavy-Duty Suspension Package, making it fantastic for someone who is seeking a fun but tough and capable off-road machine for weekend forays into the wilderness.
The Land Rover Defender is an off-road champion with a fine legacy that dates back to 1948 and the Land Rover Series. It’s rare that you find a model that’s endured for decades without much change in terms of exterior appearance, albeit with hundreds of refinements under the skin, and within the interior. That’s what the Defender – the classic one, that is – is all about. This 1996 Land Rover Defender 90 is a fine example of that statement, and you can get it from Sturbridge, Massachusetts if you wish. With just over 10,000 miles on the clock, this off-road beast packs the formidable 300Tdi powertrain, a manual transmission and a custom interior with air con and Bluetooth!
The Chevrolet Silverado’s corporate cousin is the GMC Sierra. It’s a smart move by General Motors to broaden their line-up across their various brands by sharing synergies. In fact, the Silverado and Sierra have been like this since 1999, when the Silverado became a separate nameplate. Hence, the first generation Silverado/Sierra was made between 1999 and 2007. In fact, variants like this 2002 GMC Sierra 2500 SLT were only made up to 2004, as the heavy-duty line. This particular truck has done a light 64,000 miles and is up for sale in Orange, California. It’s got a 6.6-liter Duramax diesel under the hood, a 62-gallon fuel tank, and is four-wheel drive. That makes it ideal for someone who wants a sturdy truck that can venture off-road when needed.
The RAM Pickup was originally known as the Dodge RAM, before Chrysler Corporation (now Stellantis) spun RAM off into a separate, pickup truck-only brand. The half-ton variant in RAM’s range has been the RAM 1500, which remains to this day. However, if you want a RAM 1500 that can really knock your socks off, try a TRX variant like this 2022 RAM 1500 TRX Crew Cab 4x4 Ignition Edition. With its 6.2-liter supercharged V8 banging out over 1,100 horsepower at the crank thanks to several modifications, this super-truck is definitely something to behold. We’re told that it’s got a vertical door conversion, the TRX Level 2 Equipment Group, and being an Ignition Edition, is one of just 875 produced.
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