In many ways, Jacques Villeneuve, the son of Ferrari legend Gilles Vileneuve, didn't fit the traditional F1 driver mould. The Canadian arrived on the F1 circuit as the reigning CART champion and Indy 500 winner. With his baggy overalls and blonde hair, Jacques caused a stir in F1 both off the track as well as on it. During his stint with the Williams team, Jacques bet Technical Director Patrick Head that he could take Suzuka's 130R flat, a feat that he did without coming off the throttle or left foot braking – although it did require him to drop two wheels in the dirt. After he rolled at Eau Rouge, another famously difficult corner, Jacques got out and proclaimed it was his 'best crash ever'. 

But perhaps the moment that Jacques' daredevil image was cemented was during the 1996 Portuguese Grand Prix. Earlier in the season JV had likened the last corner of Estoril to an oval track, and he used all of his previous oval experience to pass Michael Schumacher around the outside of the high-g corner. That takes guts.

- Charles Kha

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1

He also bet his mechanic that he could drive through this corner flat. But then he said he got to the overtaking position and instincts told him to go flat. Finally he said that he would never do that again seeing it now :D (from F1 Magazine)

2

hey, are these overtakes limited to 4 wheels. iv seen Valentino Rossi make some stunning overtakes on more than 1 occasion.

3

Dafty's question is an interesting one, though the motorcycle content on this site is a bit sparse, so i'm going to assume that they are all indeed of the four-wheeled variety

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