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I always say: everyone loves a classic pickup truck. While new trucks and even vintage muscle cars can be divisive, no motorhead can walk past a well-loved old truck without smiling. Why? Theyā€™re beautiful, theyā€™re cool, and some of them are very unique. Here are four old trucks you can get into for under $20, and a couple cost less than $10k.

GMC Caballero utility coupe

A GMC Caballero coupe utility muscle truck parked in a driveway.
1986 GMC Caballero | Cars & Bids

Youā€™ve heard of the Chevrolet El Camino. But did you know there was a GMC version? The 1978-1987 GMC Caballero is one of the most unique coupe utilities you can buy. Like the El Camino, the GMC Caballero was a muscle truck built on the Chevelleā€™s chassis. You could order it with any engine from an I6 up to a 454 cubic-inch V8. It also came with either an automatic or a manual transmission. Note that from 1971-77 the GMC version of the El Camino was called the ā€œSprint.ā€

How much are these unique old GMC Caballero pickup trucks worth? They donā€™t come up for sale often. But in April 2023, a 1986 GMC Caballero with a 5.8-liter V8 upgrade came up on Cars & Bids (pictured). GMC fans bid the truck up to $19,000 even. On other sites, GMC Caballeros have gone for everything from $3,300 to $27,500 with the average value being about $13k.

Volkswagen Type 2 Transporter truck

A white Volkswagen T2 bus cut into a pickup truck complete with roof rack, parked in a lot.
1983 Volkswagen T2 truck | Cars & Bids

The Volkswagen busā€“also known as the Volkswagen Transporter (or T series) is an icon. But did you know that VW cut some of these vans down into factory-built trucks? Yes, a rear-engine, RWD truck. The first-gen (T1) vans and buses are commanding stratospheric prices. The T3, released in 1979 is a bit more of a square body. Your best bet for cool-looking old VW Transporter pickup trucks is probably shopping for the T2 generation, released in 1967. Note that in 1971, VW offered a 1,200 cc engine upgrade.

In November 2022, a Volkswagen Type 2 double cab pickup truck with a diesel engine and 4-speed transmission (pictured) was bid up to $15,250 on Cars & Bids. These are relatively rare trucks, but the T3 version lists a little more often, with examples advertised currently for $22k and $24k.

Jeep Comanche pickup truck

Red 1989 Jeep Comanche 4WD old pickup truck parked on a lot, fog visible in the background.
1989 Jeep Comanche | Cars & Bids

The current Jeep Gladiator is far from the brandā€™s first 4WD pickup truck. The 1986-92 Jeep Comanche was a series of old midsize pickup trucks built on the beloved Cherokee chassis. These are one of the most unique old trucks around, but they can be bought for a bargain, and any mechanic familiar with the Cherokee should be able to service it.

The lovely red 1989 Jeep Comanche pioneer trim (pictured) sold on Cars & Bids for $13,400 in January 2022. A 1990 Jeep Comanche modified for better off-roading was bid up to $10,200 in February 2022, and another 1990 sold for $12,100 in March 2023. The average sale is $11k, while the highest sales come in at $25k, and projects still move for under $4k.

Jeep Gladiator full-size truck

Old Jeep Gladiator pickup truck parked in front of a garage door.
1983 Jeep J-10 | Cars & Bids

The Comanche was not Jeepā€™s only old pickup truck. The SJ-generation Gladiator was a full-size full-frame pickup truck Jeep built from 1962 through 1988. This truck was originally built on the Wagoneer platform, but its name went from the J-series to the Gladiator. It actually bridged the eras of Willy-owned Jeep, AMC-owned Jeep, and even Chrysler-owned Jeep (when it was canceled to not compete with Dodge trucks. So over the years you could order it with engines ranging from a 230 cubic-inch ā€œTornadoā€ I6 to AMCā€™s 401 cubic-inch V8. These are some of the most unique full-frame old pickup trucks around, and you can still buy one for a bargain.

In June 2021, a beautiful 1983 V8 Jeep Gladiator (pictured) sold on Cars & Bids for $5,432. Thatā€™s near the bottom end of the market, with $6k representing the lowest-dollar projects. The average resale is closer to $26k.

Next, find out the discontinued pickup truck brands youā€™ve never heard of or see more affordable classic trucks in the video below: