24 Classic Trucks Every Gearhead Dreams of Owning

Americans have had a long and passionate relationship with the pickup truck. While they’re available worldwide, no one really embraced them in the same way. Pickup trucks may come from a humble background as a farm or work vehicle, but automakers soon realized their true potential as a lifestyle vehicle.

While modern trucks offer all the power and amenities one could wish for, they lack the charm of a classic model. In this article, we’ll look at some of the coolest classic trucks money can buy. Considering how many different trucks have been sold, it’s almost impossible to pick only 24, but we still gave it a shot. All the trucks on this list are older than 25 years to qualify as classics.

1989 Toyota Hilux

Toyota sold the Hilux under the name Pickup Truck in North America. That makes perfect sense, and to complete the lineup, they should’ve named the Supra and Camry “Sports Car” and “Sedan,” respectively. Anyway, what makes the Hilux so great is that it’s practically unkillable.

If you’re a Top Gear fan, you may have watched the episodes where Jeremy Clarkson put it to the test. No matter what they threw at it, the Toyota Hilux just shrugged it off and kept running. It’s pretty much the gold standard for reliability.

1985 Toyota Land Cruiser J70

Regarding reliability, the Toyota Land Cruiser is one of the few trucks that can match the legendary Hilux. Toyota introduced the J70 Land Cruiser in 1984 as a replacement for the iconic FJ45.

The J70 retained its predecessor’s off-road abilities and has proven so popular that it’s still in production today, even though several generations of the Land Cruiser have existed since it arrived.

1977 Ford F-250 Highboy

Ford’s F-Series has been the best-selling vehicle in the States for decades. Since its debut, Ford has built some excellent versions, one of which is the 1977 F-250 Highboy.

What made the Highboy so great was that owners could fit a set of 35-inch wheels without messing with the suspension. Perfect for those who venture off-road regularly.

1991 GMC Syclone

The GMC Syclone was a proper high-performance truck, capable of leaving proper sports cars in its dust thanks to a turbocharged 4.3-liter V6 engine. It would reach 60 mph in 4.3 seconds from a standstill and had a top speed of 124 mph.

GM built just under 3,000 Syclones, and to be honest, they weren’t particularly good work trucks as they could only haul 500 lbs. However, they’re among the most fun trucks money can buy.

1959 Chevrolet Apache

The 1959 Chevrolet Apache was part of the Chevrolet Task Force truck series, which means it was more rugged than most of its counterparts at the time. It was also a very stylish truck, with a wrap-around windshield, lots of curves, and headlights in the fenders.

While it did look the part, the Apache was never available with 4WD from the factory, but conversion kits were available. Buying one today will set you back a pretty penny, though.

1991 Chevrolet 454 SS

Mention 454 SS to any gearhead, and they’ll think of the 1970 Chevelle. The 454 SS pickup truck is often overlooked, and while it was down on power compared to its muscle car namesake, it still has plenty of potential.

The 454 SS is a proper muscle truck, but with only 230 horsepower and 385 lb-ft of torque, it wasn’t as impressive as the Ford Lightning or GMC Syclone. Thankfully, teasing out more power from the big V8 is relatively simple, and plenty of aftermarket performance parts exist.

1978 Dodge Li’l Red Express Truck

As the malaise era had reduced the performance car market to a shadow of its former self, an American hero emerged in the form of a pickup truck. The Dodge Li’l Red Express was the fastest vehicle on sale in the States in 1978.

Dodge exploited a loophole in the emissions laws, which meant pickup trucks didn’t have to adhere to the same strict regulations as cars. Thanks to its 390 V8 engine, the Li’l Red Express could force the mighty Corvette to eat its dust.

1979 Datsun 620

The Datsun 620 pickup didn’t have the power of the Li’l Red Express, but it was still a fun little workhorse, earning it the name Li’l Hustler on the US market.

It remained in production on other continents for decades after it was discontinued in the States, and enthusiasts have modified it in every way you can imagine. Pandem/Rocket Bunny even made fender flares for it, and in combination with a Hakosuka Skyline front end, it looks seriously mean.

1974 Jeep J10

In 1971, Jeep dropped the Gladiator name for its pickup. Instead, it was just known as the J-series or Jeep truck. The J10 looked stylish yet tough, and it had a 401 V8 engine that produced a whopping 330 horsepower.

Jeep also offered the Honcho package for the sportside and short bed J10, which made the masculine truck look even more badass. It consisted of stripes and decals and also offered a roll bar.

1938 Diamond T Model 201

In the early 20th century, Diamond T Motor Car Company was started in Chicago and became known for its military trucks. Then they built the Model 201, a pickup truck that was so well-built, people referred to it as the “Cadillac of Trucks.”

The Diamond T Model 201 went on the market in 1938. The truck looked sturdy and had a beefy chassis to back it up. Early models had a Hercules 205 six-cylinder engine that produced 73 horsepower, and later, the Model 201 received a 236 engine with 91 horses.

1954 Dodge Power Wagon

The Dodge Power Wagon is essentially a military truck for civilian use, and it’s just as rugged as it looks. It’s one of the vehicles that pioneered modern 4WD systems, and combined with the big wheels and high ground clearance, there weren’t many places it couldn’t go.

This workhorse didn’t pack a ton of power, but it would tackle whatever was thrown at it—no wonder it was so popular with farmers and forest workers.

Studebaker Coupe Express

The Studebaker Coupe Express was a stunning pickup truck built in the late 1930s. It was far ahead of its time, pioneering the coupe-truck hybrid, or ute, long before the Chevy El Camino and Ford Ranchero.

Studebaker had created a vehicle that combined the driving feel of a car with the practicality and sturdiness of a truck. It was an all-steel build with a beautiful design and a comfortable cloth or leather interior.

1993 Ford F-150 Lightning

Nowadays, the Ford F-150 Lightning is an electric pickup truck, but the original was a proper V8-powered muscle truck. Whereas Chevrolet put the massive 454 V8 under the hood of its performance truck, Ford decided to play around with the 5.8-liter small-block.

With 240 all-American horsepower and 340 lb-ft of torque, the F-150 Lightning from the early ’90s could keep up with some decent sports cars. Ford also upgraded and lowered the suspension to ensure it would outhandle the Chevy 454 SS.

1964 Dodge Custom Sport Special

In 1964, Dodge offered a Custom Sport Special package for the D100. It included bucket seats, racing stripes, and other unique features. The upgrade we’re most interested in was found under the hood.

Dodge offered the Custom Sport Special with Chrysler’s big 413 wedge-head V8 in 1964, and the following year, it was available with the 365-horsepower 426 V8.

1956 Ford F-100

The Ford F-100 was the second generation of Ford’s legendary F-series trucks. It wasn’t the original and didn’t sell as many units as the later F-150, but the F-100 may just be the best-looking truck Ford has ever made.

Aside from its gorgeous design, the F-100 also ditched the old flathead engine in favor of an OHV V8 that produced as much as 167 horsepower in the 1956 model.

1952 International Harvester L Series

As the name suggests, International Harvester started out in farm equipment but ventured into road vehicles as early as 1907. IH introduced the L Series truck in 1949, and production lasted until 1952.

The L Series range included the L110 1/2-ton and the L130 one-ton truck. The L110 had a spacious “Comfo-Vision” cab, and 6.5-foot or 8-foot bed lengths were available. Those who bought the L130 could even order it with a 9-foot bed. A choice of inline-six engines was also offered, ranging from the 220 ‘Silver Diamond’ to the 269 ‘Super Blue Diamond.’

Mercedes-Benz 170 Pickup

In recent years, Mercedes wanted a piece of the lucrative pickup truck market and tried to sell a badge-engineered Nissan for a premium mark-up. It didn’t work. That wasn’t the first time M-B ventured into the truck market, though.

In the 1930s, the German carmaker built the 170 V. The “V” in its name was an abbreviation of “Vorn,” the German word for front, and it was used to separate it from the rear-engined 170. After WWII, 170 V production resumed, and until 1955, it was the top-selling Mercedes vehicle, offered in multiple body styles, including pickup, van, sedan, roadster, and cabriolet.

1962 Studebaker Champ

At the beginning of the 1960s, the Studebaker brand was no longer what it used to be. It introduced the light-duty Champ pickup truck in 1960, as the manufacturer’s truck lineup hadn’t received significant updates in over a decade.

The Champ was primarily a parts bin special, but the result was not only competitive in price it was also an excellent truck. It was the last pickup truck designed by Studebaker before leaving the car industry in 1966.

1989 Dodge Shelby Dakota

Carroll Shelby’s name is forever attached to some of the greatest American sports cars ever made. As it turns out, old Shelby was also recruited to improve on the Dodge Dakota pickup truck—as a chicken farmer, he probably had some ideas on how to make it more practical.

What he actually did when creating the Shelby Dakota was to replace the 3.9-liter V6 with a 5.2-liter V8. It still only delivered 175 horsepower and 270 lb-ft of torque, but that’s still more than most other trucks from that era. Of course, being a Shelby, it also had racing stripes.

1986 Lamborghini LM002

Lamborghini originally built the LM002 as a military vehicle but ended up making it an SUV/truck for civilian use. Powered by the same V12 engine found in the Countach, it certainly didn’t lack performance.

Unlike today’s Urus, the Rambo Lambo was never a bestseller, but we think it’s way cooler than the mass-produced Lambo SUV.

 

Willys-Overland Motors built some excellent vehicles in its day, including the Americar lineup. It was built as a pickup, sedan, coupe, and wagon and was first introduced in 1937, although the Americar name wasn’t used until 1941.

The Willys Americar pickup truck looks stunning, and seeing as the coupe is a popular choice among hot rodders, it shouldn’t be too hard to turn the truck version into something special as well.

1947 Hudson Big Boy

The Hudson Big Boy 3/4 pickup arrived on the market in 1939, and it’s a solid choice if you want a classic pickup truck. The postwar models are the most common, and production lasted until 1947.

This classic truck looked intimidating, especially in black, and it was as robust as anything from that period. It had an 86-horsepower inline-six engine, but there was a 96-horsepower unit available as an option.

Volkswagen Type 2

Everyone knows the 1960s Volkswagen Bus, and it was one of the forerunners of today’s modern cargo vehicles and vans. The Type 2 was also available as a flatbed pickup truck. However, it’s less common in the States.

In 1964, United States President Lyndon B. Johnson introduced the Chicken Tax in response to tariffs placed by France and West Germany. The Chicken Tax curtailed the import of German-built Type 2 trucks and commercial vans—passenger vans weren’t affected by it, and that’s why you’ll see the VW hippie vans but very few trucks.

1936 Chevrolet Coupe Pickup

The Chevrolet SSR wasn’t the first time the American automaker built a weird truck. In 1936, Chevy introduced the Coupe Pickup, also known as the Gentleman’s Pickup or Express Pickup. The world was still amid the Great Depression, so those who could afford a vehicle wanted to get the maximum bang for their buck.

Serving as both a family car and work truck, the Coupe Pickup certainly offered value for money.