The nine best Cadillacs ever made, is the last one convincing?

Cadillac is believe it or not one of the oldest carmakers in the world. Yet for all that endurance, on first thought, it’s difficult to pick out real stand-out models from its history, recent and distant. Especially for Europeans. But bear with. This century-old proprietor of luxury and latterly, performance, has some absolute gems in its back catalogue, be they objectively good or culturally significant. Let’s get into them.

2004 Cadillac CTS-V Gen 1

We start, weirdly for a company first founded in 1902, in 2004, with the first-generation CTS-V. This was arguably the first sign of Cadillac’s 21^st century renaissance, as a competitor to the German executive racket. With a chassis developed at the Nürburgring, 400PS (294kW) of LS6 Corvette small-block power, a limited-slip diff and a six-speed manual ‘box, it was fully equipped to give a BMW M5 a bloody nose, at the price of an M3. It looked good, too.

1959 Cadillac Series 62 convertible

Yes, in 2004 Cadillac needed to change. Because it had traded on the same soft luxury tropes that had effectively been its bread and butter for over a century. A pink Series 62 is perhaps the car that defines that ethos, with a splash of jet-age styling for good measure. Pink Cadillacs were popularised by a Mr Elvis Presley and over the following half-century, they became cars seared into pop culture. There’s both a song and a film called ‘Pink Cadillac’. It’s this era of cars that perhaps did the most to immortalise the Cadillac name.

2016 Cadillac ATS-V

Back to the modern era and the ATS-V, another genuinely great sports saloon from Cadillac. Perhaps even more significantly, it achieves this without leaning on the charm of a big growling V8. That was the preserve of the larger CTS-V. The ATS was somewhat lumbered with a 3.6-litre turbocharged V6 engine. Powerful with 465PS (342kW) but not brimming with personality, the chassis and handling did the legwork. By most accounts, a genuine alternative to the contemporary BMW M3.

1992 Cadillac Seville

Cadillacs are perhaps the only cars in the world you could give points to for being set dressing. Look at any late 1980s and early 1990s movie set in an urban American environment and you’ll see something resembling a Cadillac Seville parked somewhere in the background. For the 1992 fourth-generation model, Cadillac received a great deal of praise, too. It was the Motor Trend car of the year in 1992.

2010 Cadillac CTS-V Wagon

Cadillac’s modern era unicorn is the second-generation CTS-V Wagon from 2009, available with a manual gearbox. Yes, a 556PS (409kW) supercharged V8 rear-driven estate with a manual gearbox. Sounds like the perfect concoction, doesn’t it? Naturally, they sold barely any, so stick-shift V2 Wagons are dearly loved and rarely seen for sale.

2003 Cadillac DeVille

Another pop culture sensation, for us at least. For those of you familiar with The Sopranos, the late-model DeVille is none other than the choice limousine for the New Jersey mob. Front-driven and lumbered with the Northstar V8 as it is, it’s far from a great car objectively but it looks the part lumbering in and out of the car park at Bada-Bing.

2021 Cadillac CT5-V Blackwing

Cadillac perhaps knows the days of a tyre-ripping V8 super saloon are numbered, just as the days of the outlandish American luxury car were in the 1970s. What better time to fit its latest 5 Series fighter with a growling V8 and a manual transmission? The 670PS CT5-V Blackwing is a supercharged swansong for the super saloons we’ve known and loved. If it’s anything like what Cadillac has been churning out these past 15 years, it’ll keep M cars honest all the way to the track and beyond for chunk-o-change less.

1930 Cadillac V16

The glory days of Cadillac, for many aficionados of the brand, were the pre-war years. Its most decadent coach-built era saw Cadillac on top of the luxury motorcar world. The era when more cylinders meant more luxury, as the marque out-gunned rival V12 cars with a breath-taking V16. Want more proof that this was peak Cadillac in the traditional sense? Multi-million-dollar sales figures for V16s should fit the bill. There were plans for a new V16-engined car in 2003, previewed by the Sixteen Concept, but the financial crash of 2008 killed that dead. Appropriate, really, given the original V-16 launched not long after the Wall Street crash of 1929.

2002 Cadillac Cien

Finally, a Cadillac that didn’t quite make it but so nearly did. Originally presented as a 100^th anniversary celebration, the 2002 Cien packed a 7.5-litre V12 with 750PS (552kW) and styling inspired by fighter jets. It was a fully running vehicle too, with engineering work carried out by Prodrive. It was also very much being considered for production, with GM execs assessing the feasibility of low-volume production in the UK. TWR, Prodrive and others were considered before they got cold feet and canned it before 2002’s end. The car is latterly featured in the 2005 film The Island, set in 2019, where the car is referred to as a “V12 ‘09 Cadi, 750 horsepower $500,000 car”. Oh, if only it were.