Cadillac Sixty Special

The Cadillac Sixty Special debuted in 1938 as a design-forward, owner-driven luxury sedan. Penned by a young Bill Mitchell, it established a new market segment for Cadillac and showcased innovative styling like its thin-pillared roof and absence of running boards. It remained a top-tier model for decades, evolving through the chrome-laden 1950s and into the more restrained styling of the 1960s and 70s.

Collectors prize the Sixty Special for its historical significance and varied styling across different eras. The pre-war 1938-1941 models are design icons, while the 1957-1959 cars represent the peak of American automotive excess with their dramatic fins and extensive brightwork. Later models from the 1960s offer a more affordable entry point into classic Cadillac ownership with reliable V8 power and acres of interior space.

The market for the Sixty Special is wide, with an average sale price around $23,320. This figure is influenced by the large number of accessible driver-quality cars from the 1960s and 70s. However, exceptional pre-war models and show-quality late-50s examples can easily command prices approaching or exceeding $100,000, demonstrating strong demand for the best of the series.

Based on 69 sales, prices range from $2,500 for project cars to $101,000 for top-tier examples.