The US auto industry famously entered a period of excess in 1957, one that would peak in 1959. Leading the way was Cadillac, whose 1959 tailfins, love them or hate them, remain a benchmark for 1950s car design. Bodywork was starting down the “flivvers dripping with chrome” route in 1957 and the redesigned Fleetwood Sixty Special gave a taste of things to come. Cadillac had introduced the new X-frame for 1957, which was stronger and more rigid but also allowed cars to be lower without sacrificing interior space. The Sixty Special was changed from a four-door sedan to four-door hardtop. The 133-inch wheelbase remained the same, but the whole automobile was much lower. The vertical chrome trim was stripped off the flanks for the first time in 15 years, but the trade-off was a huge, eye-catching alloy panel that stretched the entire length of the rear fenders below the beltline.

Under the hood, the 365 cubic inch Cadillac V-8 now cranked out 300 bhp and with an optional dual four-barrel carburetor the number climbed to 325 bhp. The parking brake was changed to a foot brake, which automatically disengaged when the car was put in gear, and air conditioning was repositioned to underneath the dash instead of in the trunk. The changes paid off and the Sixty Special was a hit with 24,000 units sold, up from 17,000 the year before.

General Motors observed its 50th anniversary in 1958, but it wasn’t all festivities and self-congratulating as the market slumped alarmingly. Cadillac sales dropped from 146,841 units to 120,246 and Sixty Special sales dropped almost 50 percent, from 24,000 to 12,900, despite numerous changes and improvements including a jump in power from the 365 cubic-inch V-8 to 310 bhp and 335 bhp from the dual four-barrel option. All Cadillacs now had four headlights, and power door locks were an option, as was the advanced but distressingly unreliable air suspension. The Sixty Special was cloaked with even more trim than the year before, with the entire rear fender covered in ribbed alloy and bordered by brightwork. The grille was a fence of bright, floating “cleats”, looking almost as if the car was fitted with braces. Rubber-tipped bumper over-riders were also placed further apart. 1958, the last year for the sixth generation of the Sixty Special, was also the last year that Sixty Special script actually appeared on the car. Tailfins got more flamboyant in 1959 before the Sixty Special gradually became more restrained in its looks, so the 1957-58 cars offer the quintessential 1950s American look along with legendary Cadillac comfort and performance. It’s a combination that many enthusiasts and collectors covet.