(1967 - 1977)
Although Mazda has become synonymous with the rotary engine, they were not the first company to put the Wankel into a production vehicle. Now defunct German car company NSU was the one, and the Ro80 was their attempt that putting the engine on a family sedan. In addition to the then-revolutionary motor, the design of the car was extremely modern and forward-thinking. Sadly, the rotary engine proved to be a maintenance nightmare as suffered from countless apex seal issues —something even modern rotary owners all too familiar with— costing the company lot of money and tanking their reputation. Eventually, the company went under and was absorbed into Volkswagen Group, where design influences from the Ro80 could be observed on various Audi products.
Chrysler Airflow (1934 - 1937)
Airflow is a cautionary tale about why the auto industry should not invest in technology before consumer demands it. Designed by Chrysler engineer Carl Breer, the Airflow was one of the first cars that were designed with aerodynamic efficiency in mind. The featured a unibody construction with a sloping front grille with flush headlines, a radical departure from the boxy, horse-drawn-carriage like structures that were popular at that time. Too radical as it turned out, as people simply did not like the design. And since it was a time when fuel was extremely cheap and roads were terrible, appearance mattered more than efficiency. Combined with build quality issues on the first few cars resulted in terrible sales, and the Airflow is now considered one of the biggest failures in automotive history.
GM EV1 (1996 - 1999)
Quite possibly one of the biggest misstep in automotive history, the GM's EV1 electric coupe was a blunder that hunts the company to this day. Developed and built solely to meet a mandate by California Air Resources Board that required all major US carmaker to offer at least one zero-emission car, GM calculated they had could not make a profit with the EV1. Instead, the company built 1,100 units and leased them out for a high monthly charge of $205 to %500. GM planned to destroy the cars after the mandate was met, as they didn't expect the car to be a hit among the users. The prediction proved to be completely wrong as many of the lessees loved their car, and went as far as to offer to buy the cars from GM. These offers went to deaf ears, and GM rounded up all the cars and crushed them, with 40 deactivated units being handed out to educational institutes and museums. The move has remained a black mark on GM history ever since, as the company is now scrambling to catch up to a drivetrain technology they once the leader of.
(1986 - 1993)
From the outside, the seventh generation Buick Riviera was not too exciting. It was an average looking front-wheel-drive coupe that is only offered with a four-speed-automatic. But GM took a design approach that was frankly two decades ahead of their time and loaded the Riviera advance tech. It was the first car to feature a touchscreen infotainment system, in the form of a 9-inch black and green CRT display. Sadly, the new technology proved far too unreliable and distracting for people of the time, to the point that Buick had to stop offering the system in 1990.