I've tried to think of a list that I could actually live with. Of course, there are many supercars I wouldn't mind having, but, in terms of pure usability, I'd like some sort of variety.
1: McLaren F1
Despite the Veyron's ultimate numbers, something about the F1 just appeals to me. I've had multiple dreams about this car. Obsessed? Probably. Oh, and, it's immensely usable with its relatively ample trunk space, seating for three, and the best customer service in the world.
2: Ferrari 599
Its one fault is the singular lights in the back, in my opinion. From the side, though, the lines are sexy as hell.
3: (Insert one crazy, senseless car here) Not limited to: Pagani Zonda, Spyker C8, Lamborghini Countach
Basically, a category of car that isn't so much driveable, as ostentatious and just out-there with the styling. Something that you can laugh about. Something where they don't say "oh, he's got money" as much as "what a moron"
4: BMW M5 (or an Audi equivalent.. RWD has its faults in snowy conditions)
5: Land Rover Discovery (Need something to store lots of crap and haul other crap.. and won't break)