The 288 GTO and the Miura are part of the few cars I did not yet meet IRL but that I would really love too. I encountered F40s a few time but only one on the road. With the Mercedes W154 and the Alfa 8C coach 2.9A, there are the 3 most impressive cars I ever saw. Whatever the cars they are next to, you cannot take your eyes off those 3.
Not sure about the top 5, but high in my list there is a place for a 911 GT1 road version, and a grey Liberty Walk F458. I must say, I never liked the F458 but damned that one looked good, way better IRL than in picture. The perfect balance of "too much" with Japanese perfect execution