The Baade 152
The Germans made this airliner with the use of bomber concepts. It had outrigger wheels and a high-wing, which are great features for bombers but not for airliners. The prototype crashed after two flights and killed an entire crew. Engineers eventually saw that the fuel lines did not work during the descent and caused the engines to fail. It ended in 1961 and remains the only airliner created in East Germany.
The Rockwell XFV-12
We bet it was hard to design the first airplanes. By the ‘70s, one would think that the wealthiest aviation company would not mess up big time. However, it surprised everyone with the creation of the Rockwell XFV-12. It looked fancy with a pointed front and unique wing style. It also used “thrust augmenter wing”, which was meant to be used for vertical flight. It never took off and fly, unfortunately.