Pickups originated as functional beasts of burden, and rarely during their first 70 years did they ever venture far from that role. Sure, there were some that stood out for styling during that time, but there were relatively few specialty models – exceptions including the sleek-sided Chevrolet Cameo and Dodge Sweptside of the mid-1950s.
But after muscle cars were shorn of their appeal in the early 1970s, trucks (and vans) started to take their place as the “in” thing. Yet it was a while longer before anything really cool came out of it.
One of the first was Dodge’s “Li’l Red Truck” of 1978. Along with some neat appearance items – including tall dual exhaust stacks exiting behind the cab, semi-style – these pickups skirted some pollution requirements (they had no power-robbing catalytic converters) to become among the quickest vehicles of their day. So that was the start. And certainly one could also add the Jeep Scrambler from the early ‘80s, which was essentially a CJ7 with a short pickup bed and a removable roof.
But since those appeared (and subsequently disappeared) more than 25 years ago, we’ll start this list with trucks that came after – partly because most are ones I’ve driven during my tenure here at Consumer Guide.
13 Coolest Trucks of the Past 25 Years
1989 Dodge Dakota Sport convertible
Appeal: The first production convertible pickup since the 1930s, and it was available with 4WD. As such, it offered an attractive blend of fun-in-the-sun driving with wintertime traction in a vehicle that could haul stuff all year ‘round. Aside from the aforementioned Jeep Scrambler, I’ll bet you can’t name another vehicle more versatile.
1989 Dodge Shelby Dakota
Appeal: The “Shelby” name, obviously, but it was also the first compact pickup to offer V8 power: a 5.2-liter with 175 horses. At the time, this was probably the quickest pickup around. Only 1475 were built.
1990-93 Chevrolet 454SS
Appeal: A half-ton pickup with big-block power. The ‘90s had 230 horsepower and a 3-speed automatic, but the ante was upped the following year to 255 hp and a 4-speed auto, along with a lower 4.10 rear gear. Most were painted a sinister-looking black, but white and red were offered in the later years. Get the black one.
1991 GMC Syclone
Appeal: Pure, unadulterated speed. With a powerful 4.3-liter turbocharged V6 and 4-speed automatic combined with all-wheel-drive traction, the Syclone could blow through the 0-60 dash in under five seconds – a revelation in its day.
1999-2004 Ford F-150 Lightning
Appeal: A big pickup with supercharged power and near sports-car handling. What’s not to like? … besides the single-digit fuel economy. All were rear-drive, regular cab short beds. There was also a Lightning produced from 1993 to 1995, but it wasn’t anywhere near as fast … or special.
2004-2006 Dodge Ram SRT-10
Appeal: A big pickup with Viper V10 power and near sports-car handling – and a manual transmission. What’s not to like? … besides the cost of rear tires. The first ones were regular-cab short beds, but the next year brought an extended-cab with optional (and undoubtedly tortured) automatic. You almost couldn’t help but smoke the weenies.
2003-2006 Chevrolet SSR
Appeal: A pickup with retro styling, a retractable hardtop, and – especially in later years – a potent drivetrain. The 2003-04 models used a 300-hp 5.3-liter V8 with automatic, but the ’05 and ’06 got the Corvette’s 6.0-liter V8 with 390-400 hp along with the option of a manual transmission. Even with about 24,000 built, there is virtually no chance this truck will not become collectible.
2002 GMC Sierra C3
Appeal: Big pickup capability with midsize-sedan maneuverability. Although the GMC C3, which came only as a 4WD extended-cab, was the first vehicle to offer GM’s Quadrasteer 4-wheel steering, the innovation was later made available on other pickups and even full-size SUVs. At low speeds, it turned the rear wheels opposite the fronts for a tighter turning circle, while at high speeds, it turned them with the fronts for better stability. Those who towed also loved it. Quadrasteer never really caught on, however, mostly due to a hefty added cost, and it was dropped after 2005. A drive in an early C3 was a real eye-opener; that big pickup could cut an arc that would make a Honda Accord jealous. If you ever questioned Quadrasteer’s value, you could turn it off with a dashboard switch. All great coffee-table fodder.
2003-2006 Subaru Baja
Appeal: Took most of what was good about a pickup and combined it with all of what was good about a Subaru – including all-wheel drive, car-like handling, and decent fuel economy – to become one of the nicest-driving pickups of all time. Based on the Outback wagon, the 4-door Baja was the spiritual successor to the neat little 2-seat Brat pickup of the ‘70s and ‘80s.
2002-2013 Chevrolet Avalanche
Appeal: It had a “midgate” between the crew cab and the short pickup box that could be removed to extend the cargo area through the cab to the back of the front seats. This allowed the shortish pickup to seat five people and carry 4×8 sheets … though not at the same time. The first generation was offered in 1500 (half ton) and 2500 (3/4 ton) versions, the latter available with a big 8.1-liter V8. The second generation that arrived for 2007 was 1500 only.
2003-2006 Chevrolet Silverado SS
Appeal: Powerful V8 with all-wheel drive. It made its mark on my memory as being one of the only vehicles I ever tried brake-torquing where the brakes couldn’t completely harness the power; it would creep forward no matter how hard I pressed on the whoa pedal. And when you released it, the truck just flat left. All were extended cabs powered by a 345-hp 6.0-liter V8 with 4-speed automatic. Early models came only with all-wheel drive, but in swan-song ’06, the SS came only with rear-wheel drive.
2004-2005 GMC Envoy XUV
Appeal: An SUV that can be turned into a pickup – with the press of a button. Okay, this is perhaps stretching the definition of a “truck,” but there’s no denying the novelty of the XUV’s forward-sliding rear roof that opens the back to the sky. It also had a two-way tailgate and a retractable “midgate” that separated the plastic-lined cargo area from the passenger compartment. Studebaker originated the idea back in the early ‘60s, but that wagon wasn’t offered with all-wheel drive – or all our modern amenities.
2011-current Ram 1500 Tradesman
Appeal: 390 horsepower, $23,000; ‘nuff said … but I’ll continue anyway. These are bare-bones regular-cab pickups available with Dod … er … Ram’s 390-horsepower 5.7-liter Hemi V8. Only rear-drive at first, you could get one with 4WD in 2012. Optional Adventurer or Express packages added color-keyed grille and 20-inch alloys for a sportier appearance, and other body styles eventually became available, but all those dimmed its “sleeper” status somewhat – and its “bargain” status. Current prices are substantially higher than those of inaugural 2011, but I’m pretty sure nothing else at that time offered a better horsepower-per-dollar ratio.