Gran Turismo 4's Mercedes manufacturer history high speed chase mission (mission 34) was hell. not even Forza Motorsport 7 gave you that long a handicap.
1. Red bull X2010 Challenges in GRAN TURISMO 5 (BEFORE THE PATCH) Try doing 2 laps in Suzuka in 2:10 minutes... Doing the Nurburgring GP in 2:09 was almost equally as difficult. Monza was not hard but not as easy as it looked, especially with a controller. 2. Mission 34 in Gran Turismo 4. 123 seconds of wait everytime you fail a corner or get a penalty, and you have to drive really fast in the hardest circuit of them all in a fast and heavy car with sports tires 3. ... Hard to think of anything else, a few licenses in GT4-GT3-GT2 come to mind. Anything in GT6 was easy, Ayrton Senna's challenge with the Lotus was the hardest and it wasn't really that hard. GT5 Eiger with the Alfa 8C was hard, but even harder would be the Event where you drive a Murciélago in a REALLY DARK road where you can barely see anything, this also had to be patched.