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Aye, in honor of National Talk Like A Pirate Day on September 19th, today we be featurin’ a buccaneer’s favorite piece of steel, the Cutlass.

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(Image/OnAllCylinders & Sword cutlass2 work by EJWitek | CC BY 3.0,)

You see, long before it was used by Oldsmobile, the name Cutlass referred to a short, curved sword that was very popular for naval officers, sailors, and—of course—pirates.

But as the 1960s dawned, Oldsmobile thought that Cutlass would also be the prefect name for the upscale variant of its upcoming F-85 compact.

Yar landlubbers, this here be a reeeeal Cutlass. (Image/Sword cutlass2 work by EJWitek | CC BY 3.0)

F-85 & Beyond

The F-85 was Oldsmobile’s new entry-level model, based on the unibody GM Y-Body that also begat the 1961-63 Pontiac Tempest and Buick Special.

The F-85 first appeared in 1961. This one here is a 1964 edition. (Image/OnAllCylinders)

If you’ve never heard of an F-85, don’t turn in your gearhead card just yet. Admittedly, the F-85 naming convention gets tricky because many folks simply refer to all the Oldsmobile intermediates (including the upcoming 442) as “Cutlass.”

But there is a distinction.

While the base F-85 was an economy model, the Cutlass trim added some sportiness, along with more upscale interior and exterior appointments. Then early on, there was also the F-85 Jetfire, which was one of GM’s initial forays into forced induction. (You can read more about those early turbocharging efforts here.)

This here’s an F-85 Jetfire, which was based on the F-85 coupe, yet was given Oldsmobile’s innovative turbocharged 215 cubic inch V8. (Image/GM Heritage Center)

It’s worth noting that this new F-85 could be equipped with an Oldsmobile-tweaked version of Buick’s 215 cubic inch aluminum V8. While it was a revolutionary engine that would see decades of success later (particularly after Rover bought the manufacturing rights), the 215 was deemed too fancy for the F-85’s economy car mission and dropped after 1963.

Moving Up to an Intermediate

Those 1961-63 F-85, Cutlass, and Jetfire models were relatively slow sellers though, so GM upsized the entire Y-Body line to a new intermediate A-Body platform in 1964, to coincide with the newly-launched Chevy Chevelle.

This 1965 Cutlass shows off the lines of its larger A-Body sheetmetal. (Image/OnAllCylinders)

In addition to improving sales, the more traditional body-on-frame architecture heralded a significant push into the performance world for the F-85 Cutlass, specifically with the introduction of the fabled 442 package.

Debuting in 1964, the 442 trim was a response to the surprise success of the Pontiac Tempest GTO released earlier that year. The numbers 4-4-2 initially referred to a four barrel carb, a four-speed manual, and dual exhausts, but that rubric would evolve later as more drivetrain options began to appear.

This is a 1966 442—but changing options like a Tri-Power carburetor setup meant the numbers 4-4-2 didn’t always have the same meaning anymore. (Image/OnAllCylinders)

Meet the New Oldsmobile V8

When the Buick-sourced aluminum V8 was dropped after 1963, Oldsmobile began a new generation of iron block V8s that would propel its cars through the next several decades. Its first iteration, at 330 cubic inches, bowed for 1964 in the F-85 line.

We’ll ultimately see versions of the venerable Oldsmobile V8 contract and expand from 260 to a whopping 455 cubic inches.

(It’ll also, perhaps infamously, be converted into a diesel variant. But that’s a topic for a different day.)

The Oldsmobile A-Body came in both a coupe and convertible. And though we won’t talk about them much here, there was also a four-door sedan and station wagon offered too. (Image/OnAllCylinders)

The Cutlass Enters its 3rd Generation

In 1968, every GM intermediate got a redesign. While the F-85 name stuck around, it was quickly being overshadowed by a growing number of Cutlass subvariants, namely the Cutlass S and Cutlass Supreme.

In other housekeeping news, the 442 briefly moved into its own model designation, no longer an options package, before returning as an option on the Cutlass in 1972.

When the launch of its third generation, the Cutlass line expanded, as evidenced by this 1968 Cutlass S here. (Image/OnAllCylinders)

1968 also saw the introduction of the trusty Oldsmobile 350 V8 as a Cutlass option. The Olds 350 was an evolution of that aforementioned Oldsmobile V8, and was distinct from the Chevy, Buick, and Pontiac 350s that were released at about the same time.

The Olds 350 would wind up in plenty of vehicles, including the Vista Cruiser wagon and even a few Cadillac models. (Image/OnAllCylinders)

The next year, the Cutlass got a facelift and then in 1970, something significant happened: when ordered as a Cutlass Supreme, the Cutlass became the only GM A-Body with an optional notchback roofline—unless you count the newly-minted Monte Carlo and Grand Prix, which were only available as notchback coupes.

The notchback coupe was exclusive to 1970-72 Cutlass Supremes. (Image/OnAllCylinders)

You also may hear the Cutlass Supreme notchback referred to as a “hardtop coupe” as the steel roof mimics the side profile of the ragtop version.

You could still get the Cutlass as a traditional fastback coupe and a convertible as well.

The notchback joined the fastback coupe and convertible, also available through 1972. (Image/OnAllCylinders)

As for the F-85 base model, it soldiered on until 1972, when it was reduced to a sole four-door sedan before being ultimately dropped from the lineup altogether.

Experienced drag racers could get a showroom-fresh H/O into the 13s. (Image/OnAllCylinders)

And now’s probably a good time to mention Oldsmobile’s top-of-the-heap performance A-Body, the Hurst/Olds. Essentially a 442 cranked to 11, the Hurst/Olds was built, obviously, in conjunction with Hurst Shifters and included the mammoth Oldsmobile 455 engine.

oldsmobile rocket 455 in engine bay of a 1971 442 cutlass
The H/O’s “special edition” status helped circumvent GM’s 400ci displacement cap for intermediates, but GM soon dropped that restriction, which allowed the 455 to be added to the regular Cutlass options sheet too. (Image/OnAllCylinders – Katie Rockman)

The Cutlass Stands Alone: the Colonnade Era

GM redesigned its entire A-Body lineup again in 1973, adopting what is popularly referred to as “Colonnade” styling. It was at this point that the F-85 officially disappeared, while the Cutlass branched another trim level, the Cutlass Salon.

Though performance took a hit, the Hurst/Olds and 442 packages carried on as options under the Cutlass name too.

As seen in this 1974 model, the distinctive Cutlass split grille carried over from the second generation. (Image/OnAllCylinders)

Updates were relatively minor for the Cutlass and its submodels as the Colonnade era progressed, and perhaps the biggest revisions were under the hood, as Oldsmobile (and every other manufacturer) scrambled to find a good answer to tightening emissions laws and increasing fuel economy demands.

As you’d expect, horsepower continued a gradual slide through the mid-1970s, yet the massive 455 carried on until 1977. The 442 was still around too, though primarily as an appearance package.

The Cutlass Salon submodel was inspired by European luxury coupes, and offered an enhanced suspension and upscale interior. (Image/OnAllCylinders)

Oldsmobile sensed a winning recipe here, and the Cutlass would soon begin its march to market dominance as it became the best-selling Oldsmobile (surpassing the Delta 88) in 1975, and ultimately the best selling car in America almost every year(!) between 1976 and 1981. That feat wouldn’t be bested until the Toyota Camry began its incredible run in the late 1990s.

The “waterfall” style grill shown here on this Cutlass S arrived in 1976. (Image/OnAllCylinders)

One Big Happy Cutlass Family

The Cutlass lineage gets a little bit murky as the 1980s arrived. For starters, GM shrunk the A-body across every division in 1978 (which would soon be rechristened the G-Body), and the Cutlass grew other submodels like the Calais.

This era era also has the infamy of carrying the ill-fated Oldsmobile 350 diesel.

The Cutlass went through a transition period in the early 1980s, breaking off into various FWD submodels, while the Cutlass Supreme, like this 1980 edition, carried on with the traditional front-engine, RWD layout. (Image/OnAllCylinders)

It gets more nebulous in 1982, when Oldsmobile started treating Cutlass like a mini-marque, spawning the Cutlass Ciera and Cutlass Supreme as distinct, standalone models, then soon thereafter, the Cutlass Calais would arrive in 1985. While the Calais and Cierra were rather ordinary front-wheel drive commuter cars, the RWD Cutlass Supreme is still worth talking about.

The Cutlass Supreme is relatively easy to upgrade, making it a popular choice for grassroots drag racers still today. (Image/OnAllCylinders)

Riding on that aforementioned G-body, along with cars like the Buick Grand National and Chevy Monte Carlo SS, the Cutlass Supreme 442 and H/O could be considered some of the last body-on-frame, rear wheel drive musclecars that GM produced. As such, they were embraced by the performance community and are still common sights at drag strips across America.

1984 hurst olds h/o oldsmobile
Andy R. shared a pic of his 1984 Hurst/Olds with us a while back. It was one of the last vestiges of the musclecar golden era. (Image/Andy R. via Summit Racing)

In fact, both the 442 and Hurst/Olds packages briefly reappeared around this time, adding some throwback street cred to the Cutlass faithful. The factory powerplant of choice was a 307 cubic inch version of Oldsmobile’s familiar V8—but nowadays it’s not uncommon to see Cutlasses (Cutli?) running SBCs and even LS- and LT-series engines.

Long overlooked on the show car circuit, GM G-bodies like the Cutlass Supreme are now starting to earn some much-deserved appreciation. (Image/Summit Racing)

Sailing Into the Sunset

After a 1988 redesign, even the Cutlass Supreme found itself on a front-wheel drive platform. Yet Oldsmobile kept some vestiges of performance alive during the Cutlass’ fifth generation. At various points over its production run, you could get a five-speed transmission paired with Oldsmobile’s relatively potent Quad-IV and 3.4L V6 engines.

Ultimately though, the Cutlass would drift away as little more than a re-skinned FWD Chevy Malibu.

But the Cutlass legacy endures, as the earlier RWD models continue to rise in both value and popularity.

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Check out more Oldsmobile Cutlass photos below, Mateys:

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Author: Paul Sakalas

Paul is the editor of OnAllCylinders. When he's not writing, you'll probably find him fixing oil leaks in a Jeep CJ-5 or watching a 1972 Corvette overheat. An avid motorcyclist, he spends the rest of his time synchronizing carburetors and cleaning chain lube off his left pant leg.