10 Classic Pickup Trucks Worth Collecting


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May 20, 2023

10 Classic Pickup Trucks Worth Collecting

If you're looking to invest in a classic pickup truck, we've found some gems for

If you're looking to invest in a classic pickup truck, we've found some gems for you.

As American as baseball, apple pie, and capitalism, the pickup truck cemented itself as the quintessential American vehicle after Ford introduced the Model T with pickup body when Henry Ford discovered American farm laborers were modifying his Model T to fit their everyday, blue collar needs.

Nearly 100 years later, the pickup truck market remains America's most popular vehicle, and will grow into a market share worth over $250 billion by 2028, according to market research.

While most brand-new pickup trucks can easily run north of $100,000, many continue to turn to the ever-chaotic used car market. But with the vanishing "cheap used car" segment, buyers have to decide between sinking six figures into a car payment or investing in something with the hopes of increasing valuation.

Fortunately for you, we at HotCars completed the research and comprised a list of 10 classic pickup trucks worth collecting — that is, if you can find some of these rare gems.

It's hard to imagine a time when the GMC Syclone didn't command everyone's attention when appearing on the market — but it certainly was the case in 1991. Now, primarily praised as the prototype sport truck which paved the way for modern-day muscle trucks, the Syclone went largely unappreciated by the general public during its initial debut. From getting passed around multiple export markets, to even turning up at junkyards during the cash-for-clunkers movement the Syclone is enjoying its time in the son, and rightly so.

Once known as the fastest production truck in the world, the Syclone also boasted the first four-wheel antilock braking system in a pickup. This turbocharged 4.3-liter V6 engine combined to produce 280 horsepower and 350 lb-ft of torque while catapulting the Syclone from 0-60 in under six seconds — quicker than the Corvette at the time. Expect to fork over anywhere from $25,000 and up... if you can find someone willing to give theirs up, that is.

Unlike the Syclone mentioned above, the first rendition of the Ford F-150 Lightning was an instant success. Debuting in 1992 as a direct competitor to Chevy's 454 SS, the F-150 Lightning served as Ford's gateway truck from a blue-collar workhorse to a capable daily driver in the city. Developed by the newly minted Special Vehicles Team (SVT), the Lightning featured the venerable 351 Windsor V8 with some peppy upgrades to increase power while maintaining structural integrity through the use of high flow rate intake manifold and cylinder head, aluminum alloy pistons, and stainless steel short tube headers.

While only producing 240 horsepower and 260 lb-ft of torque, the trick up Ford's sleeve for this Lightning came in the form of a five-and-a-half foot Scottish driver by the name of Jackie Stewart. After finding himself in the winner's circle numerous times thanks to a Ford-powered race car, the Flying Scot lent his many talents during the development of the Lightning and is directly responsible for helping create the best handling sport truck of its time. Sport truck lovers can expect to pay a reasonable, $18,000 for solid examples.

Quite possibly the greatest truck marque of all time, the HiLux goes by many names depending on your part of the globe. But here in North America, referred to lovingly as the "Toyota pickup," this unkillable truck continues to roam the highways of North America decades later. While all Toyota pickups are virtually indestructible, not all our created equal in terms of collectability. That is reserved for the fourth-generation N50 chassis, more specifically the SR5 4x4 Xtra Cab.

Already known as a legend in off-road racing circles thanks to Ivan "Iron Man" Stewart and his revered PPI SR5 baja truck — the SR5 is forever immortalized thanks to its screentime in the 1985 film, Back To The Future, solidifying the humble Toyota pickup as an instant classic. Well-sorted examples continue to hover around $22,000.

If the Ford F-150 Lightning is the poster child of the sport truck movement — then it has the Chevrolet 454SS to thank. Debuting in 1990, two full years before the Lightning reached market, the 454SS was America's first sport truck since the less-than-stellar Dodge Shelby Dakota. Borrowing what is perhaps GM's greatest trim marque in the 454SS, this Chevy muscle truck used the C1500 C/K chassis as its base and proceeded to take a page straight out of the muscle cars of the '60s and '70s and stuff it with their largest production engine.

Boasting the 7.4-liter V8 found in the 3500 series C/K, the 454SS produced 240 horsepower and a monstrous 385 lb-ft of torque while featuring a multitude of other factory goodies to ensure this sport truck was more than just a huge engine on wheels. upgrading the suspension through gas-filled Bilstein shock absorbers, front stabilizer bar, fast-ratio steering gear assembly, and a higher axle ratio for its locking differential. Receiving the praise it rightfully deserves as one of the first sport trucks of all-time, clean examples can easily run close to $30,000.

RELATED: Here's What We Love About The Chevrolet 454SS

As with anything, history has a way of repeating itself — especially in the automotive history — Dodge reached deep into its bag of tricks and dusted off one of its oldest strategies. Because as history shows, while Ford and Chevrolet occupy each other's time in an endless game of top trumps, Dodge watches the action from afar while adapting the positive qualities that Ford and Chevrolet implement in their production lineup. From the original Challenger, to the modern day TRX, time and time again Dodge remains the ever-prevailing tortoise in a race against two hares.

In perhaps the response that took longest, Dodge finally reentered the sports truck market with the Viper-powered Ram SRT-10 in 2002. During a time where 1/2 ton trucks in everyday settings were becoming the norm in North America, that meant the sport truck was more popular than ever. While most were clamoring over Ford's reintroduction of the F-150 Lightning and Chevy's unveiling of the Silverado SS, Dodge burst onto the scene with the ultimate mic drop when it stuffed the Viper's 8.3-liter V10 under the hood, slapped on some racing stripes, and sent the Ram into the wind tunnel for extensive aerodynamic testing. The result is this list's youngest classic truck worth collecting, and can be had for close to $30,000.

In what is easily considered as this list's most expensive truck worth collecting, we give you: the Lamborghini LM002. More affectionately known as the "Rambo Lambo," Lamborghini's first attempt at a crossover vehicle continues to endure mixed opinion. After plans to develop a military-inspired vehicles for exploration ceased, Lamborghini debuted the V12-laden utility truck at the 1986 Brussels Auto Show to polarizing review.

Although seen as a large departure from the originator, many point to the LM002 as the groundwork foundation for the modern-day Urus — a crossover vehicle that is single-handedly responsible for revitalizing the supercar crossover craze. However, nearly 40 years later the LM002 can easily fetch upwards up a quarter of a million dollars for the few remaining examples.

RELATED: 1986-1993 Lamborghini LM002: Prices, Specs, And Features

In a day and age where high-powered six-cylinder compact pickup trucks are the norm, some may forget that there was a time where the sixces of the engine world were best described as "anemic." From terribly low power output, to a puny level of grunt and torque, compact trucks weren't nearly as capable as their full-size pickup siblings. That all changed in the late '80s when Jeep introduced their iconic 4.0-liter straight-six engine in 1986.

Now seen as one of the greatest pieces of American engineering, Jeep set out to prove it was more than capable of producing a workhorse similar to the legendary Wrangler. The result was the sport-inspired Eliminator. Offering best-in-class power, torque, and towing capability the Commanche Eliminator inched the truck world that much closer to the truck-laden highways of America we've come to know — fortunately, this piece of pickup truck history will cost you less than $15,000.

If you were to tell the blue-oval faithful in 1999, that one of the most beloved sport trucks ever engineered is due in large part to Harley-Davidson, your gearhead card would be instantly voided. However, 25 years later, it makes sense that America's two-oldest automotive institutions would come together to build a pickup truck — and it might leave you wondering how it took so long. Built for those looking for more performance than the base F-150 and a more luxury focused ethos than the Lightning, Ford delivered the Harley Davidson trim line.

Featuring a detuned version of the Lightning's supercharged Triton V8 engine, the HD F-150 managed to produce an admirable 340 horsepower and 425 lb-ft of torque with unique exterior and interior features that set itself apart from the various trim levels that became stagnant. Fans of this particular F-150 can find decent examples for as low as $20,000.

RELATED: Here's How Much A Harley-Davidson Edition F-150 Costs Today

As the Toyota SR5 found out in 1985, car makers began discovering the public's interest in off road ready compact pickup trucks — and their willingness to splash cash on them by any means necessary. After witnessing Toyota single-handedly dominate the market, Chevrolet provided what is now considered the biggest threat to the Toyota throne (at the time): the Chevrolet S-10 Baja. Exclusive to the 4x4 S-10 pickup truck, the Baja package didn't offer much in terms of performance, but what it did lack in engine prowess it made up for in off road readiness.

Featuring a roll bar equipped with lights, grille guard with fog lights, tubular rear bumper, an underbody shield package that included a transfer case, front diff, fuel tank, and oil pan shield, and upgraded suspension the Baja came factory ready to take on the city or the dirt road. If you can find one, prepare to drop close to $20,000 for a Chevy Baja today.

Touted as the original truck to blur the line between workhorse and everyday driver, the second-generation Ford F-100 Series began converting the pickup truck from a practical choice, to a lifestyle endeavor. Still regarded as the best designed truck of all time, it is not quite sure why Ford abandoned this particular design cue after only four model years — however, it remains the clear favorite of any Ford fanatic.

Known internally as the "million dollar cab" for the amount Ford reportedly paid in R&D, the investment paid off as the second-generation F-100 forever cemented the Ford pickup as the go-to truck in American folklore. With prices hovering around $35,000, you won't need to invest a million dollars in the greatest truck of all-time, like Ford had to.

Jacob is a writer and gearhead splitting time between Southern California and Phoenix, Arizona. When he's not wrenching on his and his wife's questionable fleet of cars; he's learning DIY repair, researching car culture and history, or casually browsing used cars. Jacob cut his teeth writing for the now defunct, Oppositelock, before the website was blown up.