Airline Empires has posted an interesting collection of pictures showing some of the “ugliest” planes that have actually flown. Although there are no clear winners as to which plane is the ugliest, the Caproni Ca.60 Noviplano definitely wins both the “ugly” and the “that thing actually flew” award. Featuring eight engines, three sets of triple wings and two pontoons, this flying boat was meant to be a prototype for a 100 passenger trans-Atlantic airliner. On 4 March 1921, it made one short flight over Lake Maggiore in Italy and attained an altitude of 60 feet before crashing and quickly sinking to the bottom of the lake (killing both pilots).