A yellow 1953 Cadillac Eldorado convertible at a beach

Luxury Cadillacs Age Like A Fine Wine

There’s just something about a Cadillac. The angles. The chrome. The luxury touches. For several generations owning a Cadillac has been the focal point of American luxury. Jerry Seinfeld didn’t buy his dad a Lincoln or a BMW. He bought his dad a Cadillac. Fear and Loathing in Las Vegas wouldn’t be the same without the oversized 1971 Fleetwood Eldorado. Egon, Venkman, Winston, and Ray busted ghosts in a 1959 Cadillac Ambulance. Even the original Batmobile in the 1943 “Batman” film was a 1939 Series 75 Caddy. There’s just something magical about a Cadillac, especially a classic Caddy you can call all your own. Here are just a few of the very best the manufacturer has put out over the years, with some used Cadillacs on the list a little easier to come across than others.

1908 Cadillac Model S

We’re going to kick it off with one of the models that kicked off Cadillac. The 1908 Model S shows the company has always paid attention to luxury details. From the seating to the touches of gold against the blue construction, where other companies at the time looked to simply put something out that could run, Cadillac put out something that would turn heads. It also handled better than just about anything else at the time as well. You’re probably not going to spot many of these outside of a museum (or break into Jay Leno’s garage), but it’s worth mentioning as a true classic Cadillac.

1915 Cadillac Type 51 V8

Here’s another one you’re probably not going to find driving around. We’ll be brief on this one, but we wanted to include it because it became the very first production vehicle to ever use a V8. A V8 in a mass-produced vehicle back in 1915 was unheard of. And while 70 horsepower doesn’t sound like much now, you would have outperformed anything else around you with the V8 under the hood on the Type 51.

1930 Cadillac V16

A classic used Cadillac, a red 1931 Cadillac V16 in a gray showroom

The V8 engine was few and far between at this time. So what did Cadillac decide to do? They dropped in a V16 into the car. Sure, it might not have made much sense, But a car that could produce 185 horsepower in 1930 was the ultimate in luxury performance.

Cadillac eventually went on to release a concept car in 2003 called the Cadillac 16. While they never produced it (it basically looks like if the CTS and Tim Burton’s Batmobile had a car child), it did bring back the V16 engine (with 1,000 horsepower). It’s a fun walk down memory lane if you ever want to look either the V16 or the Cadillac 16 up.

1953 Cadillac Eldorado

Following World War II, Detroit was able to turn its attention from building tanks to building cars just about the size of tanks. And with the Great Depression over people had extra money to buy these cars. The 1953 Cadillac Eldorado took this to new heights as it was pure American luxury. It was one of the first cars to use the wraparound windshield, not to mention you could see the beginning of Cadillac’s classic fin tail lights with this model. Of course, if you ever decided to go with the 1953 Cadillac Eldorado, you absolutely need to make it the convertible model.

1959 Cadillac DeVille

A closeup of the pointed taillights on a green 1959 Cadillac DeVille

Ahhh, the giant chrome fins. These fins are pretty crazy when you look at them now. There’s almost no reason for the fins to look like this, but that’s exactly why Cadillac did it. The company has never been one to be modest. After all, they were dropping V16 engines into cars for the fun of it. And the 1959 Cadillac DeVille sure is a lot of fun. The interior cabin is big enough to fit the entire family, and the trunk is also big enough to fit the entire family (although we won’t recommend testing this one out). With a bug chunky 6.4L V8 engine that produced 320 horsepower, the 1959 Cadillac DeVille remains one of the most picturesque cars ever made by the company.

1976 Cadillac Eldorado

We could probably put every single Eldorado model year up on this list. But we won’t. In many ways, the 1976 Eldorado was the end of what had made Cadillac since the 1950s. It marked the very last time Cadillac used a 500 CID V8. It was also the last convertible Cadillac made for over a decade. Why? Because this was one of the biggest cars Cadillac to this day has ever made (park next to a Chevy Silverado and you may be surprised as to which of the two is longer). Also, a convertible without any roll bars of this size is not exactly the safest model available. U.S. safety laws started to really kick in at the end of the 1970s, which is why Cadillac stopped making convertibles for an extended period of time.

1999 Cadillac Escalade

Cadillac didn’t jump into the world of luxury SUVs for a while. While other companies were producing SUVs for ages (the Chevy Suburban remains the longest continually produced vehicle in the history of vehicles), Cadillac focused on cars. However, after the end of the 1970s, Cadillac struggled with reducing the size of its cars. Markets had shifted to smaller luxury vehicles, which meant Cadillac had to completely reinvent itself and begin producing vehicles it had never really made before. The Cadillac Escalade allowed the company to finally produce something big again. And now, the Cadillac Escalade is arguably the most successful vehicle in its fleet. The newest Escalade is even using the largest OLED display ever in its 2021 release (a full 38 inches!). It’s also OLED, which is the pinnacle of display technology (more so than QLED). So when you want to go big or go home, you’ll want to go with the Escalade.

2008 Cadillac CTS-V

A red 2009 Cadillac CTS-V doing a burn out on a track

The CTS-V really is Cadillac’s way of turning back the clock. The CTS itself helped redefine what it meant to be a Cadillac. At the time, the company was struggling with the upcoming younger generation as most didn’t like the larger, bulkier Cadillacs, so the look of the CTS helped make Cadillac hip again. However, it was the CTS-V that really took it a step further (and in a way, a step back in time). That’s because the CTS-V dropped a supercharged 6.2L V8 Corvette engine under the hood. While it’s no V16, we can’t rule out they won’t try to do that again sometime soon.

What Are We Missing?

These are just a handful of the very best Cadillac models to ever come out. Of course, we could write up a blurb about nearly every single model Cadillac has ever put out, as there’s just that kind of magic revolving around the brand. But which model do you love? Is there a reason why you’ve always loved it? Maybe your granddad sat behind the wheel, and you got to ride in it a few times a year. Or perhaps you saw it drive by one day, and you swore you’d eventually own that used Cadillac. Let us know in the comments. And while you’re at it, let us know your favorite movie car as well. There’s really nothing better than a classic movie car.