Driving a 1965 Oldsmobile Cutlass After 55 Years

The 1965 Oldsmobile Cutlass F-85 coupe.

The 1965 Oldsmobile Cutlass F-85 coupe.

Ryan Tomas, Staff Automotive Editor

Imagine driving down your favorite scenic road on a perfect sunny day. The hills are green, it’s not too hot, it’s not too cold, and there’s not a cloud in the sky. You’re relaxed, one arm steering, and the other resting on the top of the door. Where are you? It doesn’t matter. What day is it? It doesn’t matter. What year is it? It doesn’t matter. The Bluetooth speaker on the dashboard is playing AC/DC and life is easy. Because you’re driving a 1965 Oldsmobile Cutlass.

The Oldsmobile Cutlass is a huge sedan based on the Chevrolet Chevelle. Even though this one is just a two-door coupe, it’s still hard to overstate this car’s size. The trunk is just as long as the hood, which is made longer than it needs to be by the six or eight inches between where the 330 cubic-inch “Jetfire” V8 ends and where the hood stops. It’s comedic almost, driving this massive car alongside modern traffic. Cars that would be considered big today look like compacts next to the Cutlass, Oldsmobile’s smallest model in 1965. 

Even though the Cutlass isn’t one of the world-famous sports coupes like the Mustang, it’s still really fun to drive. But with this car, it’s a different kind of fun. There’s no drag racing, burnouts, or drifting in this car. It’s going to the donut shop, parking right in front, and watching people look at you in confusion. It’s shifting the ancient two-speed automatic transmission into low gear on downhill offramps and hearing the backfires echo off the minivan next to you. The car’s steering is hilarious. The power steering is way overboosted, so much so that you could drive with just one finger on the blue two-spoke steering wheel. The real fun comes as a result of how slow the steering is. It takes about six turns to get all the way from left to right, so for parking lot maneuvers, you have to spin the wheel like it’s Pirates of the Caribbean. In most situations, it’s more comfortable than a modern car, especially with the wide, couch-like blue vinyl seats, soft ride, and light steering. Everything’s easy in this car.

This Cutlass belongs to my friend’s family, so one day we took it to go get some food at the McDonald’s drive-through. There was no one in the line when we got there so we went up and ordered our food as usual. We finished up our order and went to move up to the window, but right before we got there, we heard a huge bang, and steam started billowing out of the hood. I shut the engine off as quickly as possible to save the engine in case something went really wrong. When my friend and I got out and walked around to see what happened, there was a huge puddle of brown water under the car and the grille was all wet on one side. Still not sure what had gone wrong, I opened the hood to discover a hose had slid off of the radiator and poured water all over the place. 

I started the car and quickly pulled it into a nearby parking spot. Fortunately, this was the best-case scenario; the clamp was still on the hose, and a screwdriver was in the glove box, so I slid the hose back in place and tightened down the hose clamp. We then went to the nearest gas station and bought three gallons of water to refill the radiator. The engine only drank about a gallon and a half, so we kept the rest of the water in the trunk just in case something like this happened again. We got back in, started the Oldsmobile up, and went about our day. We’ve never had a problem with the hoses again.

The magic behind the Cutlass is that it defies time. Even if you or even your parents weren’t alive in 1965, you can drive this car and it will take you right back there. Back then, General Motors used to be thought of as The Establishment, your parent’s car, something you’d want to rebel against to have your voice heard. Driven by the “get off my lawn” kind of people. But now, it’s the opposite. Every new car is so focused on being different, bold, and aggressive, that the giant black Oldsmobile stands out far more than the new Hyundai Sonata ever could. It’s just like they say: everything comes full circle. What was once normal and boring is now unique. Trying to make a statement now just makes a car fit in more, so the Cutlass’ lack of crazy modern lines is what makes it special on today’s roads. It doesn’t matter where you’re going, an Oldsmobile Cutlass is your slice of freedom.