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While classic convertible cars have long held a special place in the hearts of collectors, not all were produced equally – so which are deemed to be the best?

Generally speaking, people generally buy convertibles for one of three reasons: they like the idea of open-top motoring, or they like the idea of other people thinking they like the idea of open top motoring, or because the car they really want is only available as a convertible.

Oddly enough, these sentiments aren’t exactly new – open-air motoring has been around since the very first horseless carriages. While there have been many memorable classic convertible cars that have been produced over the past century, some have more historical and cultural significance than others. 

The Best Classic Convertible Cars Of The 20th Century 

A convertible or cabriolet is a passenger vehicle that can be driven with or without a roof in place. The methods of retracting and storing the roof vary between models. A convertible allows an open-air driving experience, with the ability to provide a roof when required. 

The majority of convertible roofs are of a folding construction framework with the actual top made from cloth or other fabric. Other types of convertible roofs include retractable hardtops which are often constructed from metal or plastic, and detachable hardtops, where a metal or plastic roof is manually removed and often stored in the trunk. 

As car engines became more powerful by the end of the 19th century, folding textile or leather roofs (as had been used on victoria or landau carriages) began to appear on cars. While the major automotive manufacturers continued to quietly plug away at improving the look, feel and function of convertible models, demand for this body type began to increase from the most unlikely of places. 

During World War II,  American soldiers in France and the United Kingdom began to experience the small roadster style cars that were not available in the United States, and included iconic makes such as the MG Midget and the Triumph Roadster. As a result, United States automakers manufactured a broad range of models during the 1950s and 1960s. From economical compact-sized models such as the Rambler American and the Studebaker Lark, to the more expensive models such as the Packard Carribean, Oldsmobile 98, and Imperial by Chrysler – which are deemed to be the best of the best, and the most iconic classic convertible cars?

1961 Lincoln Continental Convertible – Although the Continental was produced on and off since 1939, it was the fourth generation that collectors have revered the most. With its famous “suicide” rear-hinged back doors, an available 462-cubic-inch V8 engine, a power convertible top, tilt steering wheel, the Continental was a marvel of engineering in its day. The 1961 Lincoln Continential’s value has since soared in value, and is considered to be a favourite for collectors.

1966-1969 Alfa Romeo Spider (Duetto, Veloce) Series I – Designed and manufactured by Italian revolutionaries Pininfarina, the Alfa Romeo Spider was the last model Battista “Pinin” Farina was involved with. Featuring a monocoque or unitized-body construction with front and rear crumple zones, the original Spider was powered by a 108-hp 1557 cc DOHC I-4, before being upgraded to a 118-hp 1779 cc DOHC I-4 engine in the 1968 release.

1958-1961 Austin-Healey Sprite Mark I –  Measuring just 137.0 inches long, the tiny two-seater was powered by a 43-hp 948 cc I-4. A rear-hinged one-piece front clip revealed the engine, while the lack of a trunk opening required folding the seats forward to access the spare tire and cargo area. The large “bug eye” headlights and “smiling” front grille has arguably made the Austin-Healey Sprite one of the most iconic British roadsters of all time. 

1959 Cadillac Eldorado – Perhaps the epitome of the over the top 1950’s automobile styling, the Eldorado is nothing short of iconic when it comes to American pop culture from a bygone era. With it’s massive tail fins and dual “bullet” tail lights, the Eldorado also featured “extras” that many other makes at the time didn’t have, such as seats, windows, locks, steering, and brakes as well as an air suspension.

1967 Ferrari 275 GTS NART Spyder – Starting with the Pininfarina-designed Ferrari 275 GTB Berlinetta (coupe), Luigi Chinetti convinced Ferrari coach-builder Sergio Scaglietti to create the 1967 Ferrari 275 GTS NART Spyder. Although only ten of these models were ever built, the Spyder had a claimed top speed of 166mph. Today, an original 275 GTS NART Spyder can fetch more than $20 million dollars on the vintage collectors market. 

1965 Ford Mustang Convertible – Needless to say, the 1965 Ford Mustang is regarded as one of the most iconic and revered American vehicles of all time – and the addition of a convertible body style only increased its notability. Thanks to it’s relatively instant success, the Mustang models ushered the dawn of a new era of “pony cars”, some of which included the Chevrolet Camaro and Plymouth Barracuda. 

1974 Chevrolet Corvette – Oddly enough, when the Chevrolet Corvette originally appeared in showrooms across the United States, it was only available as a convertible. Hardtop models began to appear in 1963 with the second-generation Corvette, while t-tops became an option with the third-generation model (1968-80). All the same, the convertible Corvettes of 1974 held strong in regards to being considered as one of the best classic convertible cars even today. 

1965 Pontiac GTO – This high performance and groundbreaking automobile was the prototype for what we now know to be the Pontiac GTO, or America’s first muscle car. Partly driven by its performance, and partly because of a very effective marketing campaign, the Pontiac GTO quickly became a sales success, particularly in regards to the first generation convertible. The Pontiac GTO is now regarded as the first – and one of the best – American muscle cars. 

1961-1967 Jaguar E-Type Series I – Often regarded as the most beautiful car ever built by vintage auto enthusiasts around the world, the early Series I models featured a 265-hp 3.8-liter I-6 and four-speed manual, while later cars received a larger 4.2-liter engine with more torque and an updated transmission. There’s always been something incredibly sexy about this car, and it even appears in the Austin Powers films as the “Shaguar”. 

1957-1963 Mercedes-Benz 300SL – Arguably one of the most glamorous Mercedes-Benz models to ever be released, the 1957-1963 Mercedes-Benz 300SL roadster is still considered to be the brand’s most famous convertible. This roadster featured a two-seat drop top with sizzling performance, all thanks to its race car-derived chassis and its 3.0 litre straight-six, mounted at a 45-degree angle to accommodate the aerodynamic styling.

Although open top vehicles are still regularly designed and released by vehicle manufacturers all over the world, nothing quite compares to driving classic convertible cars and envisioning yourself in a bygone era.