1958 Cadillac Fleetwood Sixty Special: More of everything!

The 1958 Cadillac Fleetwood Sixty Special. It was the top-of-the-line owner-driven Cadillac sedan from a year when even the standard Series 62 coupes and sedans were something to see. But as huge, silent, and flamboyant (yet elegant) as every ’58 Cadillac may have been, the Sixty Special was even better. Fins, chrome, sheer unvarnished size, and comfort. It was the Cadillac of Cadillacs.

As Cadillac’s sales brochure told us, “The moment you take the wheel … you will find a wonderful new world of motor car performance! When you turn the ignition key and that great, powerful Cadillac engine comes to life, you will sense instantly that something very special awaits you in the miles ahead.

“And you will travel with such incredible smoothness and solidity that there will be only the passing scenery and the onrushing highway to give you a sense of movement …within the first few miles you will know that this is, beyond question, automotive performance at its masterful best!”

Yes, in the late 1950s, Cadillac was king. It had it all: Looks, quality, luxury, performance, prestige. And, of course, chrome. Sheer, wild, unapologetic chrome.

General Motors could do no wrong in the ’50s; it was the 800-pound gorilla of motordom, and it showed in its unabashedly flamboyant, fantastic motor cars. Especially at Cadillac, where the Clark Street factory rapidly shipped truckloads of befinned pastel-toned confections—like this turquoise Sixty Special—to happy, affluent new owners.

While it was not the most expensive Cadillac that year (the Fleetwood Seventy-Five limousine and sedan, and the stratospherically-priced Eldorado Brougham cost more), the Sixty Special was traditionally the nicest owner-driven Cadillac, with the most chrome and longest wheelbase.

Compare the Sixty Special to the more mainstream (yet no less compelling) Series 62. Both are beautiful cars, but the Sixty Special is clearly more upscale, with a longer wheelbase, fender skirts, more mature styling, and at least 12 square feet of additional chrome!

Base price of a 1958 Series 62 sedan was $4891 (about $46,300 today), and it’s very likely that many went out the door for well over $5000, with all of the Cadillac factory options that were available. A total of 13,335 Series 62s were built.

Yes, it was the “standard” Cadillac, but this was America in the ’50s—and this was General Motors. As Broughamtastic as the Sixty Special Fleetwood was, one could be more than happy with a Series 62. It had all the style, all the room, all the comfort—just with a little less gingerbread, and a more modest retail price. But don’t call it the cheap model. After all, a plain-Jane ’58 Chevrolet Biscayne sedan with a V-8 was $2397, less than half the price of a Series 62.

The 1958 Series 62 was a fine car, no doubt about it. And yet … the Sixty Special was even better. More cash out the door perhaps, but owning a Cadillac was all about splurging anyway. And all the folks at the country club would ooh and aah!

Available only as a four-door hardtop, the defining feature was the broad, ribbed stainless steel trim along the luxury yacht’s flanks, along with matching fender skirts.

“The spacious new interior appointments and furnishings are luxurious and gracious in every detail,” the brochure said, “with every motoring convenience in constant attendance—even the front ventipanes are now power-operated.”

“The distinctive and tasteful interiors of the Fleetwood Sixty Special are upholstered in subdued tones of light gray, light blue, or beige Mojave cloth, or in light gray, light blue, or beige broadcloth …”

“… and in seven beautiful selections of exclusively patterned nylon and metallic leather.” This, from the prestige brochure issued to Cadillac dealers that year. Yes, with the top-of-the-line Cadillac, you most certainly had the luxury of choice.

The 1958 Sixty Special Fleetwood had a base price of $6232 ($59K today)—$1300 more than the Series 62 four-door hardtop. No small amount in the late ’50s. To put it in context, add a zero to the MSRPs, and you’ll get a better idea of the divide, price-wise.

The Sixty Special had a curb weight of 4930 pounds, and 12,900 were built for the year. All of them, like every single other Cadillac offered for 1958, were powered by a V-8. Said engine was an OHV 365-cubic-inch unit with 310 horsepower at 4800 rpm. It was topped by a Carter Model 2862S four-barrel carburetor.

But wait, there’s even more! The Eldorado engine, which featured triple two-barrel carburetors and 335 hp, was also available as a factory option. Other fine Cadillac accessories included a six-way power seat ($103), Sabre spoked alloy wheels (set of five, including the spare, $350), air conditioning ($474), power door locks ($35 on coupes; $57 on sedans), and EZ-Eye tinted glass ($46).

This was the final year that Harley Earl, GM’s Styling VP, was fully in charge. Though Earl was nominally responsible for all GM cars, of course Cadillac was his baby. The 1958 GM cars took a lot of flak at the time for being overdone, overly chromed, and just way too busy, in general, aesthetically.

When you got to the point in your life that you could own a Cadillac, it meant a lot. It meant you made it, you were a success, and you could up a tad and enjoy life. Whether that meant you were a successful CPA, a retired attorney, or a hard-boiled Texas oilman was immaterial. You were a Cadillac Man. You’d made it. So enjoy it. And for many, 1958 was their year. What could be better than a new Sixty Special in your driveway?

(All of these photos were taken by my friend Jayson Coombes. The solid turquoise Fleetwood was at the Cadillac LaSalle Club grand national meet held in San Marcos, Texas,back in 2018. The pictures of the two-tone Fleetwood were taken at the 2019 CLC Fall Festival car show at the Gilmore Museum. Thank you, sir!)