Pickups truck are as synonymous with American automotive history as muscle cars from the Detroit Three. Over a century old, the pickup truck segment started when companies like Ford and Dodge made light trucks for the masses. Today, pickups trucks remain the best-selling segment in the entire American market, and have a fan following all over the world. Along with the likes of Ford and Dodge, Chevrolet, too, was always at the forefront of pickup truck development, making some of the most memorable pickups of all time.

In over a hundred years of history, Chevy has made some truly iconic vehicles, ones that live in the hearts and minds of gearheads across generations. Many of these vehicles were their trucks, which were untouchable when it came to power and performance, while some even locked heads with the best supercars of their time. Amazing both in value and specs, here are 10 of the best and most iconic Chevrolet pickup trucks of all time.

RELATED: GMC Blue Chip Series: A Detailed Look At The Chevrolet Task Force

10 Chevrolet Half-Ton 1938

Chevrolet Half Ton Truck 1938
via MecumAuctions
 

It had almost been two decades of pickups being popular among the masses, and the segment had moved on from merely cutting down sedans. Now, pickups were their own separate models, and had a dedicated customer base.

Chevrolet Half Ton Truck 1938
via Mecum Auctions

Thus, in 1938, Chevrolet launched a brand-new model dubbed the Half-Ton. Designed and engineered from the ground up as a truck, the Half-Ton ran on an extremely durable and reliable straight-six engine with a body that was quite the looker. With its new sleek body, the '38 Chevy Half-Ton was an instant and massive hit.

9 Chevrolet Task Force 1955

Chevrolet Task Force Truck 1955
via modelcarmag.com

After the end of the second World War, Chevrolet launched their 'Advanced Design' lineup of trucks. GM was hell-bent on ushering in a new era for pickups in America, and they made their trucks innovative, dependable, and they made the Task Force trucks.

Chevrolet Task Force Truck 1955
via Hagerty.com

An absolutely revolutionary lineup of pickups, these trucks had the most modern designs yet, and they came with a huge range of V8 engines under their hoods. Even though the Task Force truck lineup was on the market between 1955 and 1959, gearheads across generations remember the Task Force as one of the coolest trucks ever.

8 Chevrolet El Camino 1959

Via Bing
1959 Chevy El Camino

The El Camino is a legendary nameplate across America. The half-car and half-truck came onto the scene in 1959, and Chevy engineered it to go head-to-head with Ford's Ranchero. Even though the pickup truck segment had really matured into its own where manufacturers had dedicated trucks, Chevy built the El Camino on a car's chassis.

1959 Chevrolet El Camino
Via Mecum Auctions

This gave the El Camino superb road manners, and the half-truck part of the vehicle gave it surprising capability and tow capacity. The Camino proved itself to be an extremely practical car. In fact, a decade later, Chevrolet gave the El Camino an 'SS' treatment, which made it one of the first muscle trucks ever made.

7 Chevrolet C-10 Fleetside 1967

Chevrolet C10 Fleetside Truck 1967
 via GM

Ask any old school gearhead about the best looking Chevy pickup ever, and almost every single of them will name the '67 Chevy C10 Fleetside. They're not all that wrong either, as the truck was one of the first pickups to use metallic paint, and the bright red metallic paint job is one that adorned the posters of many rooms.

1967 Chevrolet C10 Fleetside
FavCars

The second generation models of the C10 Fleetside were the best-looking, and the interiors certainly matched the exterior in terms of luxury, insulation, carpets, and chrome fittings. Not only were the second-generation C10 Fleetside trucks some of the most beautiful trucks at the time, they were also one of the most technologically advanced for their time.

RELATED: Here's Why The 2023 Chevy Colorado Pickup Is A Game Changer

6 Chevrolet C30 One-Ton Dually 1973

Chevrolet C30 One-Ton Dually
source: 240 Cars

One of the largest (and longest) trucks to ever come off a Chevrolet assembly line, the Chevrolet C30 One-Ton Dually imprinted itself into the minds of customers and gearheads by way of its design alone. In fact, the C30 One-Ton Dually was actually the very first Crew Cab Dually from Chevy to ever hit the market.

Chevrolet C30 One-Ton Dually
source: 240 Cars

The truck had unrivaled space and functionality, making it the go-to truck for families that wanted a heavy-duty yet practical truck in their driveway. The Dually's rough and rugged design was what began the trend for customers to consider pickups for both work and leisure, something that holds truer than ever almost half-a-century later today.

5 Square Body Chevrolet C/K 1973

Chevrolet C/K 1937 Square Body
via hemmings.com

Chevrolet introduced the C/K truck in 1973, but most people affectionately know it as the 'Square Body'. Many might not remember the C/K name, but most certainly will recognize the term 'Square Body'. Chevy produced the truck for almost a decade-and-a-half. After all, it was just so well-designed and practical.

Chevrolet C/K 1937 Square Body
via stateofspeed.com

The '73 Chevy C/K came with both 2WD and 4WD, and came with a wide range of configurations. For the engines, Chevy offered six-cylinder, V8, and V8 diesel options. The ruggedness of the Square Body trucks proves itself by the fact that it was made into a military vehicle and saw great overseas sales.

RELATED: Why Chevy Should Bring Back The Square Body

4 Chevrolet 454 SS 1990

Chevrolet 454 SS 1990
via Mecum Auctions

Quite possibly one of the most iconic Chevrolet pickup trucks ever made, the Chevrolet 454 SS completely rejuvenated the muscle truck market in 1990. Based on the regular Silverado, the truck came with a massive 454 V8 engine, a heavy-duty suspension, and most importantly, it only came in black.

Chevrolet 454 SS 1990
via ls1tech.com

What makes the 454 SS even more significant is that this was the last time Chevy used the classic 454 V8 power mill. The most performance-focused Chevy pickup truck before the turn of the century, the truck's 7.4-liter V8 threw it from 0 to 60 in just 7.7 seconds. That was a might impressive figure back in 1990, and the 454 SS blended power and practicality like none other.

3 Chevrolet Silverado Z71 1999

1999 Chevrolet Silverado ZL1
via favcars

When it comes to pickup trucks, the Chevy Silverado is truly a household name across the 50 states. The Silverado came right before the end of the 20th century, and Chevrolet loaded it with every single feature and spec they knew customers clamored for. It was also one of the most reliable trucks on the market, basically guaranteeing the Chevrolet Silverado's success.

1999 Chevrolet Silverado ZL1
via favcars

Over time, the Silverado only built upon its strengths, as Chevy updated it constantly with more room, improved chassis, and better handling over the years. From the 1999 model years, the Z71 package stands out, as it offered unrivaled towing capabilities with an even better suspension package.

RELATED: These Are The Most Powerful V8 Pickup Trucks Ever Made

2 Chevrolet Colorado ZR2 2017

2017 Chevrolet Colorado ZR2
Chevrolet 

The mid-sized Colorado is one of Chevrolet's most popular and successful models, and the American market most certainly loves it. While the ZR2 is synonymous with the most capable off-road machinery Chevrolet has to offer today, it is only 5 years old. Chevrolet first launched the Colorado ZR2 in 2017, armed with a 3.6-liter V6 that churned out 308 horsepower and 275 lb-ft of torque.

2017 Chevy Colorado ZR2
Chevrolet

The ZR2, in its first year alone, proved itself to be a worthy off-roader, thanks to its compact dimensions, Multimatic DSSV shocks, a 2" lift, and electronic locking differentials on the front and rear. Dependable and affordable, the Colorado ZR2 has truly cemented itself as a badass truck in the American pickup market.

1 Chevrolet Silverado HD 2020

2020 Chevrolet Silverado HD
Chevrolet

The trend set by the Chevrolet C30 One-Ton Dually all the way back in 1973 holds truer than ever before today. Every pickup truck worth its salt today blends luxury and practicality, packed with luxury amenities and features. Perhaps the perfection of this model from Chevy is the 2020 Silverado HD.

2020 Chevrolet Silverado HD2500
Chevrolet

A big truck, the Silverado HD is a massively robust truck which commands an equally massive road presence. The Chevy Silverado HD 2020 remains one of the best options today, which is suitable for the most rugged of construction sites as it is while cruising along in luxury on the interstate.