Mark Twain famously said, “History doesn’t repeat itself, but it often rhymes.” This can be especially true in the automotive world, such as Cadillac taking on Bugatti. Twice. Seventy years apart.

In 1930 Cadillac launched a new flagship. The Cadillac V-16 was a incredibly limited edition model. Over 11 years, just 4,076 were made. This exclusive custom car was on par with Bugattis of the day, such as the Type 57 grand touring coupes with their straight-eight engines.

Fast-forward to the early 2000s: VW had bought the Bugatti brand name in 1998 and was rumored to be working on an ultra-luxurious supercar to revive it. With Volkswagen already developing a mid-engine Audi supercar (the R8), it was obvious that the new Bugatti (the 2003 Veyron with its monstrous W16 engine) would debut at a price point above even Ferrari and Lamborghini.

Rumor had it that Ford and Chrysler were also working on high end supercars. They both happened to be mid-engine and turbocharged, designed for track use. The Ford GT would go into production in 2004. The Chrysler ME-412, with its 12-cylinder Mercedes engine, would never see production. But Cadillac executives couldn’t have known this. They just knew they needed a halo car.

GM went all-in on a Cadillac concept. It sent two Gen-4 LS V8s to Katech Engines (a private company that builds engines for the Corvette racing team). Engineers were able to join the engines into a single 13.6-liter V16. Cadillac claimed the engine could make 1,000 horsepower and 1,000 lb-ft of torque.

Around this engine, Cadillac designed a hulking front-engine, RWD sedan. Its hood was, of course, Cruella DeVille lengths. Instead of opening like normal, it had a power-assisted “butterfly” orientation, swinging open on both sides. This is a classy 1930s design cue.

The Cadillac Sixteen had a dramatic body crease echoing the butterfly hood’s center line. This was a design cue more in line with the 1967 Eldorado. The car also debuted GMs multi-cylinder deactivation technology, giving it a 16 mpg rating. Not too bad for a 5,000 pound car with a four-speed automatic!

The Cadillac Sixteen debuted at the 2003 Detroit Auto Show and made quite the splash. Rumors swirled about it going into production. Later, the halo car morphed into a front-engine, RWD, “Ultra Luxury Sedan” (ULS or XLS) with a V12 or even a big V8. But as Bugatti, Ford, and Chrysler revealed mid-engine halo car concepts, Cadillac seemed to waffle on the Sixteen. In the end, it used this concept car’s dramatic styling to inspire the Cadillac CTS.

Cadillac finally released a halo car with its Celestiq EV. This four-door lift back will start at $340,000. While it is an incredible and luxurious electric supercar, it doesn’t do much to differentiate itself from its competitors with Rolls-Royce and Bentley badges. I have to argue, something more along the muscular lines of the Sixteen–even with EV power–would have been a halo car that was also uniquely Cadillac.

Next, learn more about how Chrysler almost built a Corvette-killer, or see the Cadillac Sixteen reveal for yourself in the video below: