With a swashbuckling, buccaneering name like Cutlass, you might be led to believe that the Oldsmobile Cutlass was a full-size land yacht. However, it actually started life in 1961 as a compact, before becoming a midsize, personal luxury car in 1968. Yes, it’s named after the sword of the same name, but also draws nomenclature from an aircraft of the time, the Vought F7U Cutlass. Six generations of Cutlass were made, and Oldsmobile also started using Cutlass as a sub-brand in 1982. Sadly, neither Oldsmobile nor Cutlass are around today, which makes this third-generation, 1970 Oldsmobile Cutlass Supreme all the more valuable as a classic American automobile. This car comes with all maintenance reportedly up to date as well, making it a great future investment.
This 1970 Oldsmobile Cutlass Supreme SX flaunts its lines with a red paint job, punctuated by a white top. That top is actually a power-operated soft top, because this car is a convertible. Then, you’ve got a set of five-spoke wheels in red and silver, wrapped with Cooper Cobra Radial G/T tires. Meanwhile, the hood features a duo of black stripes atop its power bulges, and these continue down the trunk lid as well. And as you’d expect for a ʼ60s era car, there’s plenty of chrome to look at. The interior of this 1970 Oldsmobile Cutlass Supreme SX comes with woodgrain trim, full instrumentation, a heater and ventilation system, and an AM/FM stereo with 8-track player option. We also see a USB input since this retro-styled head unit is actually a modern one, and there’s also a discrete knob for adjusting bass level. Moreover, the cabin is a pleasant place to lounge in, seated atop plushly upholstered white leather seats. There even appears to be an air conditioning unit placed beneath the dashboard for cool air on warm days.
Sporting a massive 455ci naturally aspirated V8, this 1970 Oldsmobile Cutlass Supreme SX isn’t lacking in power. This engine was introduced for the 1970 model year, and powers the rear wheels through a 3-speed automatic transmission. The car also comes with power steering and drum brakes.
The Oldsmobile Cutlass Supreme was one of the best-selling nameplates in America during the 1970s and 1980s, and by 1984 the Brougham trim represented the pinnacle of personal luxury in the lineup. This 1984 Oldsmobile Cutlass Supreme Brougham, showing 83,404 miles, captures that era perfectly with its unmistakable blend of comfort, chrome, and V8 power. Built during a time when personal coupes ruled American roads, the Cutlass Supreme offered buyers a refined alternative to sportier muscle cars, emphasizing smooth cruising, upscale appointments, and distinctive styling. With its classic proportions and well-preserved presentation, this example stands as an authentic representation of mid-1980s American luxury.
Available from 1961 until 1999, Oldsmobile’s Cutlass has got to be one of this iconic American brand’s longer-running nameplates. The name Cutlass is derived from a fighter jet of the late Forties, the Vought F7U Cutlass. The aircraft in turn was named after the nautical sword known as a cutlass. So, there’s a bit of nomenclature history for you, since it’s likely that you, your parents, and grandparents have encountered an Olds Cutlass at some point. Today’s 1964 Oldsmobile Cutlass F85 Restomod is a second-generation example that’s received a few upgrades to make it nicer for regular driving duties. These include a reupholstered leather interior, air conditioning and an aftermarket stereo system. You also get the original owner’s manual with the sale of this Redmond-based American classic.
The Oldsmobile Cutlass is a car that’s named after a fighter jet which was named after a nautical sword! Isn’t that interesting? Made between 1961 and 1999, the nameplate has been seen in the compact, midsize and personal luxury segments over time. Earlier generations such as this second-generation 1967 Oldsmobile Cutlass Convertible were solid midsize contenders in their time. This particular car packs under 96,000 miles and a potent 455ci V8, this car is a 442 Tribute conversion. With its aftermarket suspension and TH400 3-speed automatic gearbox, it’s a pretty pleasant car to take out on a regular basis. If you’re interested, the car currently rests in Belleville, Illinois.
The 1965 Oldsmobile Dynamic 88 Convertible captures the essence of mid-1960s American cruising, blending bold styling with smooth V8 performance. As part of Oldsmobile’s full-size lineup, the Dynamic 88 offered a perfect balance of luxury and everyday usability, and this convertible variant adds an extra layer of open-air enjoyment. Showing over 91,000 miles, this example presents as a well-preserved classic with timeless appeal. Finished in red over a black interior, it delivers a striking and period-correct color combination, while the desirable 425ci “Super Rocket” V8 ensures it has the power to match its presence.
Oldsmobile’s flagship full-size offering, the 88 soldiered on from 1949 until 1999, across ten generations. It was popularly considered to be a fine family car, and that’s likely where this 1950 Oldsmobile 88 Sedan began life seventy six years ago. The car comes to you with a suitably Fifties black suit, a nice white interior and a healthy 70,041 miles on the odometer. It’s got the famous Rocket V8 under the hood, hooked up to a 4-speed Hydra-Matic automatic transmission! Yes, a four-speeder in 1950, how lavish. So if you’d like to cruise around in a car from the Fifties and see what driving was like way back then, this car is up for grabs in West Palm Beach, Florida.
Searching for a personal luxury car that’s a bit unusual and lesser-known? Why not try this fine Turqoise-colored 1968 Oldsmobile Toronado from Raton, New Mexico? It’s got under 58,000 miles on the clock, a 455ci V8 up front and a nice period blue interior. Coming from the first generation of Toronado, you might be surprised to hear which end does the driving – hint; it isn’t the rear axle. Yes, that was one of the Toronado’s quirks, but there are many more unique features to discover. So, get in touch with us ASAP if you’d like to acquire this Sixties American classic.
The 1973 Mercedes-Benz 450 SL represents the beginning of the iconic R107 generation, a platform that would go on to define luxury roadsters for nearly two decades. Showing 27,315 miles, this example stands out with its striking Signal Red finish and classic Bamboo interior—an unmistakably period-correct combination. Known for its durability, smooth V8 power, and timeless styling, the 450 SL quickly became a symbol of success and refined motoring in the 1970s. With both a removable hardtop and a soft top, it offers year-round usability, making it as practical as it is collectible.
The 1982 Pininfarina Spider 2000 Turbo represents a rare and fascinating chapter in Italian automotive history, blending classic roadster styling with early turbocharged performance. With just 20,875 miles, this example stands out as a well-preserved survivor from a time when turbocharging was still a novelty in sports cars. Unlike the standard Spider 2000, this variant features a turbocharger system developed by Legend Industries, making it a unique and limited-production offering. Finished in Cherry Red over a tan interior, it captures the timeless elegance of Pininfarina design while offering a more spirited driving experience than its naturally aspirated counterparts.
The 1968 Chevrolet Chevelle SS Coupe stands as one of the most recognizable muscle cars of its era, combining aggressive styling with serious big-block performance. This example, showing 85,854 miles, benefits from being a true SS396 car, making it especially desirable among enthusiasts and collectors. While it retains its iconic identity, this Chevelle has been thoughtfully upgraded with a built 396ci V8 and supporting performance components, giving it a stronger, more responsive driving character than stock. Finished in a custom yellow exterior over a black interior, this Chevelle strikes a balance between classic muscle presence and street-ready performance, making it an ideal choice for someone who wants to drive and enjoy their investment.
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