Some of these were successful, others not so much, but all will be remembered for their incredible boldness.
As great as it is, NASCAR is not a motor sport where you see a lot of innovation, so these winged Mopars truly stand out. They were the first stock cars to play with downforce, the first to hit 200 MPH, and they were so good, they were banned from the sport. What's more, ChryslerCo had to build road car versions of these, which were total sales flops.
It's still one of the biggest gambles in NASCAR history, and one that created a legend.
Audi in the 1980s was not the company that they are now; they were a niche player overshadowed by BMW and Mercedes-Benz. Entering rally – a sport that favored rear wheel drive – with an all wheel drive car was insane, but Audi redefined the sport. Even getting Audi to sign off on this plan required years of work within the company in secret.
Suggested By: Autojunkie, Photo Credit: Getty Images
In 2004 the Lola B2k/10 wasn't a competitive race car, so Taurus Sport Racing decided to install a Volkswagen V10 TDI motor modified by Caterpillar (yes, that Caterpillar, the one that makes bulldozers) and enter it in Le Mans.
The car quickly retired because of a gearbox failure (too much torque), but it did foreshadow Audi and Peugeot's diesel LMP1 cars to come.
Suggested By: themanwithsauce, Photo Credit: Getty Images
Reader cybershrike has the unlikely story about an F1 Champion
"At the time, it seemed like a pretty huge gamble. The  Honda was a nightmare: they had no real level of competition and started development on the car that became the BGP001 early, but they'd also made the decision it was going to be the final season so you can't imagine development resources being thrown at it.
Then in steps Ross Brawn, who'd rustled up the required money to buy it, line up a couple of sponsors to keep the team going and take it over. I'll admit to thinking it was going to be a mid-pack team due to the team woes, but I probably wasn't the only one. Brawn made it work, despite all the many challenges that were faced, pretty big gamble that paid off massively."
Suggested By: cybershrike, Photo Credit: Getty Images
Here's the abridged version: Roger Penske went behind Chevrolet's back to strike a deal with Ilmor and Mercedes to make an engine solely to win the 1994 Indy 500. They exploited a loophole to make a turbocharged engine that made over 1,000 hp, nearly 200 more than any competitors.
Al Unser Jr. crushed the competition with the 500i engine, which was summarily killed off by the series organizers. Read the whole story here.
There were a handful of dually F1 cars before the P34, but none with twin front wheels. The thinking was that by having two small front wheels, the car would have a greater contact patch and less drag.
It was competitive for a minute, but Goodyear couldn't make tires that were up to the task. Even still, an incredibly bold move for a smaller team competing against Ferrari and McLaren.
There are very few race car manufactures as crazy as Chaparral, and the 2J was arguably their craziest car. This doorstop looking thing had two fans driven by a snowmobile engine in the back, which sucked the car down to the road to the tune of 1,000 pounds of downforce at any speed.
Amazingly, it worked. The problem was that Chaparral was first plagued by reliability issues, then by their rivals McLaren. They had the SCCA ban the 2J since they felt it would allow Chaparral to dominate Can Am. McLaren went on to rule the series.
There's not much crazier than a turbine powered race car with the driver and engine sitting next to each other, but this car is exactly that. Carroll Shelby called it "hogwash," but Parnelli Jones nearly won the 1967 Indy 500 with it, only to retire with gearbox issues.
Many argue that Ford took a huge risk with the GT40 program, going head to head with an experienced rival Ferrari. Ford really only risked embarrassing themselves. The thing is, Ford was flush with cash when they developed the GT40, and it was Ford that spent big bucks promoting their own program in the media.
When Porsche developed the 917, they were a tiny company by comparison, and they had never built a top-level prototype car. Going for an outright win at Le Mans for them was even riskier than what Ford did. Somehow, Porsche managed to pull off overall victory, and create a legend.
Suggested By: Kyle, Photo Credit: Porsche
You've probably never heard of the Ford Sweepstakes before, and that's ok, but you should know about it because it's the car Henry Ford bet the company on.
Literally, he bet the whole company on it. When his fate in the auto industry was at its least stable, he himself raced this car against one of the most established car builders in America (Winton) and won. That's what got investors to line up, eventually leading to the start of the Ford Motor Company.
Welcome back to Answers of the Day - our daily Jalopnik feature where we take the best ten responses from the previous day's Question of the Day and shine it up to show off. It's by you and for you, the Jalopnik readers. Enjoy!
Top Photo Credit: Getty Images