The Cadillac Sixty Special represents a significant chapter in automotive history, embodying luxury, innovation, and distinctive styling. For collectors and enthusiasts, pinpointing the "best" years is crucial for investment potential, driving pleasure, and historical significance. This guide dives into the specific years of the Sixty Special production run, highlighting standout models and identifying years that may present more challenges.

Cadillac Sixty Special: A Year-by-Year Breakdown

Year(s) Highlights Potential Drawbacks
1938-1941 First Generation: Groundbreaking "Turret Top" styling, longer wheelbase than standard Cadillacs, luxurious interiors, powerful V8 engine, trendsetting design. Considered highly desirable for their unique pre-war aesthetic and rarity. Pre-war technology requires more specialized maintenance, parts can be difficult to source, potential for rust issues due to age, less powerful than later models, hydraulic brakes less effective than later power-assisted systems.
1942 Wartime production, limited numbers, distinctive grille design. Rarity makes it highly collectible. Wartime material restrictions may have impacted build quality, extremely rare, increasing restoration challenges.
1946-1947 Post-war continuation of pre-war design, reliable engine. A relatively affordable entry point into classic Cadillac ownership. Styling is less dramatic than pre-war models, parts availability can still be challenging, similar maintenance requirements as pre-war models.
1948 Second Generation: Introduction of tailfins, redesigned body with integrated fenders, more modern styling. A significant design shift for Cadillac. Early tailfin designs are subtle compared to later, more flamboyant years.
1949-1953 Continued refinement of tailfin styling, available Hydra-Matic automatic transmission, increased engine power. Represent a good balance of classic styling and improved performance. Some consider the styling less iconic than the 1957-1959 models.
1954-1956 Redesigned bodies, wraparound windshields, more prominent tailfins. A period of significant styling evolution. Can be prone to rust in certain areas, some mechanical components may require more frequent maintenance.
1957-1958 Third Generation: Iconic tailfin design, luxurious interiors, powerful V8 engines. Considered by many to be the pinnacle of Cadillac styling. Complex electrical and mechanical systems can be challenging to maintain, higher prices due to desirability, potential for rust.
1959 Most extreme tailfin design, distinctive styling. A highly sought-after and iconic year. Similar challenges to 1957-1958 models, potentially even more complex due to the extreme styling, very high prices.
1960 Redesigned front end, toned-down tailfins, cleaner styling. A transition year between the flamboyant 50s and the more restrained 60s. Less iconic than 1959, but still desirable for its classic Cadillac features.
1961-1964 Fourth Generation: More restrained and elegant styling, improved ride quality, powerful V8 engines. A good choice for those seeking a classic Cadillac with more modern driving characteristics. Styling may be considered less exciting than earlier models, some components can be difficult to find.
1965-1970 Fifth Generation: Longer wheelbase, more luxurious interiors, available automatic climate control. A comfortable and spacious classic Cadillac. Larger size can make parking and maneuvering challenging, potential for rust in certain areas, emissions control systems can impact performance.
1971-1976 Sixth Generation: Even larger size, less powerful engines due to emissions regulations, lower compression ratios. Less desirable due to performance limitations and styling changes. Significant performance reduction compared to earlier models, large size, potential for rust, complex emissions control systems. These years are generally considered less desirable by collectors.
1977-1980 Seventh Generation: Downsized bodies, improved fuel economy, more modern styling. A more fuel-efficient and practical classic Cadillac. Styling is less distinctive than earlier models, smaller size may not appeal to all buyers.
1981-1986 Eighth Generation: Continued downsizing, available diesel engines (avoid), less luxurious interiors. Generally considered the least desirable years for the Sixty Special. Poor build quality, unreliable diesel engines (best avoided), less luxurious interiors, styling is not particularly appealing. These are the years to generally avoid.
1987-1993 Ninth Generation: Front-wheel drive, more modern technology, but less distinctive styling. A departure from the classic Sixty Special formula. Front-wheel drive may not appeal to classic Cadillac enthusiasts, styling is less distinctive than earlier models, potential for electronic issues.

Detailed Explanations

1938-1941 (First Generation): These years represent the genesis of the Sixty Special. The "Turret Top" styling, a seamless integration of roof and body, was a revolutionary design element. The longer wheelbase provided ample rear legroom, setting a new standard for luxury sedans. The V8 engine delivered smooth and reliable power.

1942: Production was curtailed due to World War II, making the 1942 Sixty Special a rare and sought-after collectible. The distinctive grille design sets it apart from pre-war models.

1946-1947: These models were essentially continuations of the pre-war design, offering a more affordable entry point into classic Cadillac ownership. While not as visually striking as some later years, they retain the charm and prestige of the Sixty Special.

1948 (Second Generation): The introduction of tailfins marked a significant turning point in Cadillac styling. The redesigned body, with its integrated fenders, gave the Sixty Special a more modern and streamlined appearance.

1949-1953: These years saw continued refinement of the tailfin design and improvements in engine power and transmission technology. The Hydra-Matic automatic transmission offered smoother and more convenient driving.

1954-1956: The evolution of tailfins continued, becoming more prominent and angular. Wraparound windshields provided improved visibility and added to the futuristic styling.

1957-1958 (Third Generation): Many consider these years to be the pinnacle of Cadillac design. The iconic tailfins, luxurious interiors, and powerful V8 engines made the Sixty Special a symbol of American automotive excellence.

1959: The 1959 Sixty Special featured the most extreme tailfin design in Cadillac history. This year is highly sought-after by collectors for its distinctive and flamboyant styling.

1960: A transition year, the 1960 model featured a redesigned front end and toned-down tailfins, signaling a shift towards more restrained styling.

1961-1964 (Fourth Generation): These years saw a move towards more elegant and understated styling. Improved ride quality and powerful V8 engines made the Sixty Special a comfortable and capable luxury sedan.

1965-1970 (Fifth Generation): The Sixty Special grew even larger, offering even more interior space and luxurious features. Available automatic climate control added to the comfort and convenience.

1971-1976 (Sixth Generation): These models suffered from reduced engine power due to increasing emissions regulations. The large size and less appealing styling make them less desirable to collectors.

1977-1980 (Seventh Generation): Cadillac downsized its models in response to the energy crisis, resulting in a smaller and more fuel-efficient Sixty Special.

1981-1986 (Eighth Generation): These are generally considered the least desirable years for the Sixty Special. Poor build quality, unreliable diesel engines, and less luxurious interiors detract from the classic Cadillac experience. Avoid the diesel engines at all costs!

1987-1993 (Ninth Generation): A significant departure from the classic Sixty Special formula, these models featured front-wheel drive and less distinctive styling.

Frequently Asked Questions

Which is the most iconic Sixty Special year? The 1959 model, with its extreme tailfins, is widely considered the most iconic.

Which years are best for collectability? The pre-war models (1938-1941), the 1942 wartime production, and the 1957-1959 models are highly sought-after by collectors.

Which Sixty Special years should I avoid? The 1981-1986 models, particularly those with diesel engines, are generally considered the least desirable.

Are parts readily available for older Sixty Specials? Parts availability can be challenging for older models, requiring specialized suppliers and restoration expertise.

How much does a classic Sixty Special cost? Prices vary widely depending on the year, condition, and rarity of the model. Expect to pay significantly more for the most desirable years.

Conclusion

The Cadillac Sixty Special boasts a rich history, with certain years standing out for their design, innovation, and collectibility. While the 1950s models are often considered the most iconic, earlier and later years offer unique appeals. Ultimately, understanding the nuances of each generation helps enthusiasts make informed decisions and appreciate the enduring legacy of the Cadillac Sixty Special.