The Tupolev Tu-144
In the 1970s Tupolev Tu-144 was created as a supersonic airliner. Sadly, the prototype crashed and was a huge failure during the Paris Air Show. It flew around 55 times but that was all because they decided to stop using it.
The Dassault Balzac V
This was another flight that seemed great on paper but when put into action, it did not work as high as expected. The French were interested in joining the vertical plane train and take the design idea from the Mirage III. During the first run, two pilots were killed. However, they did not give up yet. They tried again two more times and again crashed. Thankfully the pilot survived.