An interesting name for a car – Cutlass. Yes, that’s what Oldsmobile called their compact car offering between 1961 and 1999. In 1964, the Cutlass graduated to the midsize segment, and also dabbled around as a personal luxury car between 1968 and 1988. That’s what we’ve got here, a third-generation 1968 Oldsmobile Cutlass S Convertible from San Antonio, Texas. The third generation saw some major changes, including fresh and more dynamic styling by Stan Wilen, different wheelbases for two and four-door variants, and some nice V8 power. The Cutlass S was the midrange trim, bookended by the F-85 beneath and the Supreme above. Today, this car is a fine way to relive the glorious Sixties of American automobilia, and do so with a machine from a celebrated brand that’s sadly, no more.
This 1968 Oldsmobile Cutlass S Convertible wears a nice coat of blue paint, but what will really strike you is its interesting frontal design. The angular, jutting-out nose section is framed by triple headlamp clusters that see the parking lamps in the center, flanked by circular headlamps on either side. It sure makes for an interesting face to look at. The rest of the car is pretty standard Sixties stuff, with a long body, considerable overhangs and chrome. Plenty of chrome. At the rear, things taper downwards into a very sleekly terminated tail, with a sizable chrome bumper and slimline taillamps. This car also has some nice alloy wheels. The interior of this 1968 Oldsmobile Cutlass S Convertible is accessed via frameless doors that are very cool, and offers leather upholstered seating for up to four adults. You’ve got a full gauge pack, a thin-rimmed steering wheel and an Oldsmobile-branded push-button radio. A closer look at this radio reveals it to be quite sophisticated for the time, allowing you to adjust the front-rear speaker balance (what we call the fader today), as well as various modes to optimize sound output depending on content – think like equalizer presets. We also see a Vintage Air heating and air conditioning control panel, indicating that this car is equipped as such. A peek under the hood confirms this, with a clearly visible air conditioning compressor.
This 1968 Oldsmobile Cutlass S Convertible is reported to pack a 350ci V8. We aren’t told if it’s a 2-barrel or 4-barrel carbureted version, but either way there’s more than enough grunt on tap. Power goes to the rear wheels via an automatic gearbox.
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 1966 Ford Fairlane 500 Convertible is a standout example of classic American open-top motoring, elevated by the presence of a desirable GTA-spec 390ci V8. Showing 11,364 miles on the odometer, this Fairlane blends vintage styling with thoughtful upgrades that enhance both reliability and driving enjoyment. The GTA engine—originally associated with Ford’s performance-oriented Fairlane GT/A models—adds an extra layer of appeal, delivering strong torque and smooth power delivery. Finished in light blue metallic over a blue interior with a white convertible top, this car embodies the spirit of effortless cruising with a performance edge.
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 1971 Chevrolet Nova Coupe represents one of the most iconic platforms of the American muscle car era—lightweight, aggressive, and endlessly customizable. Showing just 1,656 miles on the odometer (true mileage unknown), this example has been transformed into a well-executed restomod that blends classic styling with modern performance upgrades. Finished in a deep blue exterior over a black interior, this Nova carries the unmistakable presence of a street machine, enhanced by SS badging and a cowl induction hood. With upgraded brakes, interior enhancements, and a built small-block V8 under the hood, this car offers an engaging driving experience while maintaining its vintage appeal.
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