The 11 Best Old Oldsmobile Cars of All Time
From the dominant Cutlass to the muscle car pioneer 88, these are Jerry’s top 11 old Oldsmobile Cars
Written by Cameron Thiessen
Reviewed by Jessica Barrett
Table of Contents
- What makes an old car great?
- 11. Oldsmobile O4 (2001): The future that never came
- 10. Oldsmobile Custom Cruiser (1971-1992): One of the great classic station wagons
- 9. Oldsmobile Cutlass (1961-1999): The name everyone remembers
- 8 & 7. Oldsmobile Starfire (1961-1966; 1975-1980): A name so nice, they used it twice
- 6. Oldsmobile Jetfire (1962-1963): The “first” car with a “turbocharged” engine
- 5. Oldsmobile 442 (1968-1971): Essential, classic muscle
- 4. Oldsmobile Toronado (1965-1970): The front-wheel-drive guinea pig
- 3. Oldsmobile 98 (1941-1996): Oldsmobile’s most luxurious muscle
- 2. Oldsmobile Model R (1901-1907): The original Curved Dash Oldsmobile
- 1. Oldsmobile Rocket 88 (1949-1996): The first muscle car
- How to find affordable car insurance for your Oldsmobile
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You might not see many Oldsmobiles on the road anymore, but some of their best vehicles range from the pioneer
Oldsmobile 88
to the quintessentially-nineties Cutlass Calais 442 W41.In 2004, more than a century after the beginning of the original Olds Motor Vehicle Company,
Oldsmobile
was laid to rest by General Motors, never to see a new model released again. Car enthusiasts everywhere mourned the loss of an American muscle dynasty, still remembered as one of the most important brands in the history of the auto industry. You better buckle up, because where we’re going, seatbelts weren’t necessarily installed in the vehicles!
Jerry
, the #1 rated car insurance
app, is firing up the way-back machine for a look at all the coolest old Oldsmobile models that we ought to never forget!
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What makes an old car great?
Cars have never been created equally—that’s why we’ve always held races to see which ones are the fastest, which ones can turn the sharpest corners, which ones can accelerate the quickest, and so on…
The average new car in 2022 will perform far better than any car from the 1960s. But those who purchase old cars do so because they’re enthusiasts looking to drive a piece of automotive history. A great old car is a piece of history that has been well maintained and is still a unique experience to drive—or maybe even just look at, depending on how iconic it is.
Historical impact and reputation are the primary criteria we’ll be using to bring you our definitive list of the best Oldsmobile vehicles of all time.
11. Oldsmobile O4 (2001): The future that never came
At the 2001 Detroit Auto Show, Oldsmobileunveiled a daring O4 concept car—a 4-door convertible sport compact car that was meant to draw the same sort of crowd as Mazda’s adorable
Miatas
.It was based on the German-made Opel Astra, equipped with a 4-cylinder 190 hp engine and a manual transmission. Also notable on the O4 was its eclectic “info ring” for managing switches and dials using LCDs in a ring around the steering column.
Unfortunately, the O4’s ‘04 debut never came, as General Motors announced the discontinuation of the Oldsmobile brand that same year.
P.S. The “O” stands for “Oxygen.”
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10. Oldsmobile Custom Cruiser (1971-1992): One of the great classic station wagons
Despite not always being the best at what they did, Oldsmobile was always a bit ahead of the curve. Their flagship station wagon following the legendary 88 Fiesta, the Custom Cruiser—not to be confused with the older numbered Custom Cruisers—is one of the most iconic-looking cars, specifically for its wood-grain exterior siding.
But what set the brand ahead of the curve with the Custom Cruiser was the introduction of the first powered tailgate in automotive history—not completely automatic, but enough power to assist in moving it with one’s hand easily.
The Custom Cruiser’s GM siblings were the Buick Estate, the Pontiac Safari, and the Chevrolet Caprice.
9. Oldsmobile Cutlass (1961-1999): The name everyone remembers
Oldsmobile Cutlass
can refer to a lot of things, from model names like the Cutlass Calais 442 W42 of the early ‘90s all the way back to its first usage on a show car designed in 1954.For most of its history as a model, the Cutlass was Oldsmobile’s entry-level car—a mid-size base model that would give rise to a few of the other vehicles mentioned on this list.
The sixth-generation Oldsmobile Cutlass is the last place the name was used. In 1999, the car was essentially just a fifth-gen
Chevy Malibu
. It, along with many other Oldsmobiles of its era, simply didn’t sell well, leading to the eventual discontinuation of the entire brand.8 & 7. Oldsmobile Starfire (1961-1966; 1975-1980): A name so nice, they used it twice
The first-generation Oldsmobile Starfire of the early ‘60s was an entirely different car than the second generation Starfire of the late ‘70s—so it’s only fitting that both make this list.
The first would go on to be the predecessor of the Delta 88 and featured some of the most iconic luxury two-door looks of the hippie era.
But the second-generation Oldsmobile Starfire subcompact 2-door hatchback is a truly peculiar piece of history for a company known for its muscle. It was exceptionally small, and ran on a similarly small I4 engine—but because of excess room under the hood, it was easy to upgrade into a racing fiend.
A simple swapping-in of a more powerful V8 engine—which Oldsmobile eventually offered as an option before discontinuing the model in 1979—could get a ‘79Oldsmobile Starfire zipping down the track.
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4.7/5 rating on the App Store | Trusted by 5+ million customers and 7 million cars4.7/5 app rating | Trusted by 5M+ drivers6. Oldsmobile Jetfire (1962-1963): The “first” car with a “turbocharged” engine
The Oldsmobile Jetfire might just have one of the coolest names in automotive history, and it certainly succeeds in calling to mind exactly what sort of car this short-lived beast was.
Its claim to fame was a T5 turbocharger, a unit bolted straight onto the engine that used a special sauce called “rocket fluid” (methyl alcohol mixed with water) sprayed into the air intake. While the whole thing didn’t really catch on in the muscle car era, it marked the beginning of a form of technology that revolutionized the way combustion engines function.
5. Oldsmobile 442 (1968-1971): Essential, classic muscle
Initially introduced as a top-level trim for the 1964 Oldsmobile Cutlass, the 442 (or 4-4-2) became its own standalone model in 1968. The name referred to its 4-barrel carburetor, 4-speed manual transmission, and dual exhaust.
The 442’s muscle legacy was pushed forward by friendly competition with another one of GM’s divisions,
Pontiac
, which made the first move in 1965 to shirk GM’s engine size restrictions for mid-size cars.In many ways, the 442 took opportunities to subvert the muscle car genre, offering what ended up to be a well-rounded, balanced car with almost sporty handling. It also offered drivers surprisingly good fuel efficiency, with a “W32” package that featured an engine specially tuned for both performance and fuel economy. The legendary 1968 Hurst/Olds was a souped-up 442 that could accelerate from 0-60mph in 5.4 seconds.
But by far, the coolest 442 ever was the 1971 Oldsmobile 442 W-30, the 442 model’s last hurrah. They’re highly sought-after by collectors, selling for prices well over $150K.
4. Oldsmobile Toronado (1965-1970): The front-wheel-drive guinea pig
Sure, the Oldsmobile Toronado may not have been the safest, most reliable, most well-known, or most futuristic Oldsmobile—but it earns its high spot as a forerunner in the development of front-wheel drive technology.
The Toronado was supposed to match the staying power of the Ford Thunderbird, but as a guinea pig of experimental engine, transmission, and drivetrain placement, it was ultimately too unreliable and dangerous to continue to exist.
Ultimately, it gave way for other cars that could do FWD—and muscle—a bit more reliably. A shame, given that the Toronado may be one of the best-looking cars ever made.
3. Oldsmobile 98 (1941-1996): Oldsmobile’s most luxurious muscle
While it may not be at the top of the list, the Oldsmobile 98 or Ninety-Eight lasted through over 50 years of production as Oldsmobile’s flagship full-size luxury car.
When it debuted in 1941 as the Custom Cruiser 98 along with the soon-to-be-extinct Custom Cruiser 96, it immediately established itself as a highly competitive car.
It returned to production after WWI to solidify its place at the top of Oldsmobile’s lineup in 1946, to be replaced by the
Aurora
exactly 50 years later, in 1996.2. Oldsmobile Model R (1901-1907): The original Curved Dash Oldsmobile
It may not have been a muscle car, but the Oldsmobile Model R—also known as the Curved Dash Oldsmobile—is a true historical icon. It’s considered to be the first mass-produced automobile as it was made on an assembly line.
A Curved Dash produced a total power equivalent to that of 5 horsies, but Ransom E. Olds’ Pirate Beach Racer was recorded to have hit a record speed of 54.38 mph in 1903.
1. Oldsmobile Rocket 88 (1949-1996): The first muscle car
As far as historical significance is concerned, the 1949 Oldsmobile Rocket 88 is by far the most iconic and important vehicle ever made by the GM brand. Many historians and racing enthusiasts credit it as being the first muscle car. It was also the inspiration for what many rock and rollhistorians consider the first rock and roll record, “Rocket 88” by Jackie Brenston and his Delta Cats.
Not only did the Rocket 88 have a lasting impact on the entire muscle car genre—a mainstay of today’s auto industry—but it also managed to dominate NASCAR in 1949. In its first year of racing, it won 6 out of 9 races that season.
The original Rocket style would go on to see new iterations until 1996, just three years before the discontinuation of the 88 line of Oldsmobile cars.
How to find affordable car insurance for your Oldsmobile
If you have an old Oldsmobile model sitting back at the ranch, it just might be a piece of muscle car history waiting to be restored. And if you plan on driving it, you’re going to want to insure it. You may even be able to get special
collector’s rates
on your insurance—and Jerry
is the place to find the best rates on a policy.All you have to do is download the #1-rated mobile app, set up your profile by answering a few questions, and be amazed as you’re bestowed with the power of choice with customized quotes from top insurance companies.
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