The Jeep Grand Cherokee, introduced in 1993, quickly became a hallmark of American SUVs. Slotting into the midsize category, it bridged rugged off-road capability with the comfort and luxury expected from a family SUV. Over the years, it evolved through various generations, adopting advanced safety features, premium interiors, and powerful engines…all while maintaining its adventurous spirit. Among its model years, some stand out for superior reliability and owner satisfaction. Here are seven of the best Jeep Grand Cherokee years and why they’re worth considering.

1998 Jeep Grand Cherokee

The 1998 model closed out the first generation of Grand Cherokee with a bang. One of its highlights was the introduction of the 5.9L V8 engine in the Limited trim, which delivered a then-impressive 245 horsepower and 345 lb-ft of torque. This engine was praised for its smooth power delivery and robust towing capacity of up to 6,500 pounds. At the time, it was dubbed one of the fastest SUVs on the market.

Its Quadra-Trac all-wheel-drive system provided excellent grip in challenging conditions, and many owners loved its simplicity and reliability. The 1998 model also had fewer electrical issues compared to earlier years of the same generation. Additionally, it maintained its rugged charm with a solid rear axle and durable suspension, making it an excellent choice for off-road enthusiasts.

2004 Jeep Grand Cherokee

The 2004 Jeep Grand Cherokee was the peak of the second generation (1999–2004). It offered an improved 4.7L High-Output V8 engine capable of producing 265 horsepower and 330 lb-ft of torque, making it a standout performer in the midsize SUV class. This engine provided an excellent balance between power and reliability.

Key improvements included a redesigned interior with better ergonomics and more comfortable seating, which addressed some earlier complaints. Safety also improved, with optional side curtain airbags that enhanced protection in rollover incidents. Owners reported fewer major mechanical issues than with earlier models, and its durable drivetrain continued to impress. The 2004 model year earned a reputation for reliability, making it a solid investment for both new buyers and used-car shoppers.

2008 Jeep Grand Cherokee

In 2008, the Grand Cherokee saw updates that made it a well-rounded SUV. This year introduced an optional 3.0L turbo-diesel V6 engine, capable of producing 215 horsepower and a remarkable 376 lb-ft of torque. This engine was highly efficient, offering up to 24 MPG on the highway, which appealed to long-distance travelers.

Safety took a leap forward, with standard side airbags for both front and rear passengers, earning the Grand Cherokee improved crash test ratings. The 2008 model was equipped with advanced 4×4 systems like Quadra-Drive II, which provided excellent off-road capabilities. The refined interior, quieter cabin, and better ride quality also enhanced its appeal. These upgrades helped it stand out as one of the best choices in its generation.

2011 Jeep Grand Cherokee

The 2011 Jeep Grand Cherokee was a game-changer. As the first year of the fourth generation, it featured a complete redesign that introduced a more refined unibody construction. This change significantly improved ride comfort and on-road handling while maintaining Jeep’s off-road reputation.

The 2011 model introduced the 3.6L Pentastar V6 engine, delivering 290 horsepower and 260 lb-ft of torque. This engine was lauded for its reliability, efficiency, and smooth performance. Buyers also had the option of the 5.7L HEMI V8, which provided even more towing capacity and power for adventurous drivers.

Interior upgrades were notable, with soft-touch materials and a modern design that gave the Grand Cherokee a luxurious feel. Safety features like electronic stability control, roll mitigation, and advanced airbags earned it high ratings from the IIHS. With fewer reported issues than later years, the 2011 model stands out as one of the best in the lineup.

2014 Jeep Grand Cherokee

The 2014 Grand Cherokee received a mid-cycle refresh that improved both performance and technology. It featured a new eight-speed automatic transmission across all trims, which enhanced acceleration and fuel efficiency. This change addressed complaints about the older five-speed transmission, making the SUV smoother and more responsive.

The 2014 model also introduced an updated Uconnect infotainment system with a larger touchscreen and intuitive controls, a big hit with drivers. Safety features like adaptive cruise control, forward collision warning, and blind-spot monitoring brought it up to par with competitors.

For off-road enthusiasts, the 2014 model retained advanced systems like Quadra-Trac and Quadra-Lift air suspension, allowing drivers to adjust the ride height for different terrains. This versatility, combined with strong engine options like the 3.0L EcoDiesel V6 and the 5.7L HEMI V8, made the 2014 Grand Cherokee one of the most versatile and capable SUVs on the market.

2018 Jeep Grand Cherokee

The 2018 model year brought more technology and performance options than ever before. This year featured the high-performance Trackhawk variant, equipped with a supercharged 6.2L V8 engine producing an incredible 707 horsepower. This made it the most powerful production SUV at the time.

For everyday buyers, the base and mid-level trims offered reliable and efficient engine options, including the 3.6L Pentastar V6 and the 5.7L HEMI V8. Safety was a key focus, with features like automatic emergency braking, lane-keeping assist, and adaptive cruise control becoming standard on higher trims.

Interior improvements included premium materials, enhanced noise insulation, and upgraded infotainment. Buyers praised its smooth ride and versatile performance, making the 2018 Grand Cherokee a top pick for families and enthusiasts alike.

2021 Jeep Grand Cherokee

The 2021 Grand Cherokee marked the end of the fourth generation, benefiting from a decade of refinements. This model year offered an impressive array of trims, including the luxurious Summit and the rugged Trailhawk, catering to a wide range of buyers.

Advanced safety features like pedestrian detection, full-speed collision warning, and lane departure warning became standard, adding to its appeal. The interior featured premium options like quilted leather seating, real wood trim, and a state-of-the-art infotainment system with Apple CarPlay and Android Auto.

Off-road capabilities remained a highlight, with systems like Quadra-Drive II and a terrain management system ensuring the Grand Cherokee could tackle any challenge. Owners consistently reported high satisfaction, particularly with its smooth ride, upscale feel, and reliability.

If you’re looking for a good used Jeep Grand Cherokee, be sure to check out MotorBiscuit’s seamless car buying tool to compare prices and find the best deal in your area.

These Jeep Grand Cherokee model years excel due to their combination of reliability, safety, and features. They avoided significant issues like the transmission problems that plagued some models (e.g., 2005 and 2015) as documented by CarComplaints.com. Safety ratings from the IIHS and NHTSA consistently reinforce their robustness in crash tests, while owner feedback from J.D. Power highlights their comfort and durability. Whether you’re drawn to off-road adventure or daily driving, these models often deliver enduring value.