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A red 1980s Jeep Wrangler YJ is shown after leaving a Jeep dealer.

Ranking the Five Funnest Jeeps

Since their debut in the 1940s, Jeeps have represented a timeless piece of Americana. Throughout years and advances in the automotive industry and countless models flooding the market, Jeep has maintained its iconic look and feel. Where does one even begin when looking at the lineup available at a Jeep dealer? So many Jeeps are eye-catching. Everything from the grill to the headlights to the shape represents fun and adventure. Jeep grew over the years and became a cult classic. Regardless of how the brand continues to grow, it will always hold its place as an industry leader in fun and 4×4. Let’s take a look at five favorites and how they’ve left a lasting impression.

#5 – Wrangler YJ

Coming in at number five is the Wrangler YJ. Made famous by the Jurassic Park franchise, the YJ became a symbol of adventure throughout the 1990s and still evokes its influence on the masses. Whether you’re running away from a dinosaur or not, the YJ impresses with its off-road capabilities. As a successor to the Jeep CJ, the Wrangler didn’t change the look too much, keeping most of the frame and body.

What did change was the addition of creature comforts that helped bring the model more into everyday driver territory. The YJ burst onto the scene in 1987 with an enhanced interior and lowered chassis, making climbing in and out of it easier than taller models. The following year, Jeep added locks to the half-doors and better seals for the soft tops. Sway bars were added for improved handling while still maintaining the leaf spring suspension of the past.

#4 – Willys MB

At number four is the Willys, and more specifically, the Willys MB. It’s hard to talk about remarkable Jeeps of the past without mentioning the original Willys models. As the vehicle employed by the Allied powers in WWII, its contributions are bigger than most to the automotive industry. These were the early years of Jeep as a company, and boy, did they come out swinging. The use of the Willys MB by the US military grew the brand’s popularity and extended its recognition to worldwide status. The 1941-1945 builds represent the first modern off-road vehicles and inspired an industry in its infancy to consider cars for more than just the road.

Built with an 80-inch wheelbase, a fold-down windshield, and four-wheel drive, the Willys MB met requirements set forth by the military to carry a 660 lb payload while not exceeding a curb weight of 1,300 lbs. While its 60 hp and 105 lb-ft of torque may not seem like a lot, it was revolutionary for the 1940s. The body was designed to be completely open, allowing soldiers to quickly jump in and out as needed. The fold-down windshield served as an opening for shooting straight ahead. Every part of the exterior design served a purpose, including the paint. The MB’s dark green was a special paint that was flat and unreflective, allowing for better camouflage. Finally, the wheels were affixed for easy field repair and the durability to cover serious ground while fully deflated. Overall, the Willy MB is not only iconic but heroic.

#3 – Gladiator

At number three, we’ve got the Jeep Gladiator pickup truck––but not just the one you can find new at Jeep dealers today. The original Gladiator was a trailblazer, both literally and figuratively. In 1962, Jeep introduced its “J” lineup of trucks. The Gladiator name was dropped in 1971, but the truck itself is something special. Originally built with the same powertrain as the Wagoneer, it was Jeep’s first foray into the pickup segment.

The truck went away in 1988, only to return in 2005 as a prototype of what Jeep’s future might hold. The prototype featured an open-air canvas top, a zoomy 2.8L 4-cylinder diesel engine, and an expandable truck bed. Once the updated Gladiator actually became available to buy 15 years later, it became a staple in its class and showed up on streets across America.

The unique thing about the new Gladiator pickup is its open-air driving, the signature feature that makes it a Jeep. How many trucks can say they come in hard and soft top options? But most notably, the Gladiator ranks best in class for its whooping 1,700 lb payload and a towing capacity of up to 7,650 lbs.

#2 – Grand Cherokee Orvis Edition

One of the highest-selling Jeeps of all time is the Grand Cherokee. In order to narrow down the model, we chose the Orvis edition as number two. It has a 4.0L straight 6-cylinder engine that roars at 190 hp standard. It also had an option for a 5.2L V8. Orvis, the Vermont-based fly-fishing equipment and outdoor clothing retailer, teamed up with Jeep as a marketing tactic. For Jeep, the collaboration served a similar purpose: introduce loyal Orvis shoppers to the brand by creating a model suited to their needs.

The Orvis trim was just slightly more expensive than the Grand Cherokee Limited. It came adorned with a Moss Green exterior, with Maize gold and Roan red stripe accents. The detailing doesn’t end there. The Moss Green accents extended to the aluminum wheels, with Orvis Edition callouts on the front doors and Orvis medallions on the door panels. It came with a specially designed spare-tire cover with a storage net and pockets on the outer surface to appeal further to outdoorsy clientele.

#1 – Wrangler TJ

Coming in at number one is the 1997-2006 Wrangler TJ. Easily the most recognizable of the bunch, the TJ is the iconic Jeep to win them all. It’s got the open-top, off-roading appearance that is synonymous with Jeep. With a rugged chassis, four-wheel drive, and a variety of powertrains, it’s the perfect companion for exploring dirt pits, climbing steep hills, and navigating the great outdoors. During its years in production, its best available engine was a 4.0L 6-cylinder 190 hp engine.

It’s really the TJ’s wilderness capabilities that make it stand out. With coil spring suspension, it glides smoothly across varying terrain. The TJ is built with impressive capabilities and velvety smooth handling. From 1999 and beyond, a 19-gallon gas tank kept drivers in the great outdoors for longer. Finally, there’s no mistaking the look of those round headlights, peering through the woods and lighting the way to adventure.

Lots More Fun Ahead

Whether your Jeep is driving through city streets, national parks, or foreign lands, it’s ready for anything. From the classic Wrangler YJ of the 1990s that paved the way for the TJ to the Gladiator trucks that became the favorite daily drivers of so many Jeep fans, Jeep has many rugged models. It also has specialty models like the Grand Cherokee Orvis Edition with its unique stylings, creating a splash in the lineup. Finally, there are the legendary Willys models that made themselves incredibly helpful in WWII efforts.

We’re impressed with the five models mentioned but are just as excited to see what the future holds. Undoubtedly, Jeep will continue to produce hits and models that we can’t wait to rank against the best and brightest. Modern Jeeps are the product of years of growth and development, taking the blueprints of the past and improving them for the future. Drivers and passengers alike can count on more adventure ahead.