#2 Nigel Mansell - Portugal 1989
Nigel Mansell had a very good qualifying session and started the 1989 Portuguese Grand Prix from the third place. Driving the Ferrari, the Briton was in the thick of things and had lived through a great tussle at the top of the field. He led the race on lap 34 before entering the pits for a change of tires.
Mansell misgauged his pace and overshot his designated spot. He later reversed the car inside the pitlane to park in position. This was a clear violation of the rules, and the Briton received a black flag from the stewards later in the race.
Controversy erupted when Mansell did not comply with the stewards and continued a fierce battle with Ayrton Senna. The two collided forcing early retirements, which not only ended the Brazilian's chance for a podium but also ruined his chances to win the 1989 world championship.
#1 Hans Heyer - Germany 1977
Hans Heyer's black flag at Hockenheimring during the 1977 German Grand Prix is easily the most memorable black flag incident in F1's long history.
The German was a renowned touring car driver at that time before he tried to test his skills in Formula 1. With minimal experience in F1 cars, Heyer had an abysmal qualifying session, which ensured that he would not qualify for the race.
However, Heyer started the race, and the race marshalls did not raise an objection to it. The German put some laps around the track before a gearbox problem forced him to retire. Following that, he was disqualified and was credited DNQ, DNF and DSQ in a single race.