Might as well make a serious attempt:

New Cars
2011 Maserati Gran Cabrio $157 980
2011 Mercedes E-350 Coupe $48,850 (though I'd prefer one of the Euro diesel versions)
2011 Aston Martin Rapide $199,950
2011 Audi A8 L $84,000 (Again would choose diesel but not sold in USA)
2011 Audi R8 V10 Spyder $172,800
2011 Chevrolet Camaro LS $22,680 (Steel wheels on this model are cool)
2010 Ferrari 458 Italia $225,325
2011 Land-Rover Range Rover $94,615
2011 Lotus Evora $64,000
2012 Ford Mustang GT Premium Convertible $38,045
2011 Peugeot RCZ GT200 $42,642
2011 MEV Rocket M225 $26,648

Classics/Used Cars
1971 Jensen Interceptor SIII $40,000 (Slightly high estimate based on UK prices)
1970 Chevrolet Chevelle SS $88,990 (Based on: http://www.oldride.com/classic_cars/131010.html)
1997 Rover 820 Vitesse Sport Coupe $3,000 (Despite being for that market never sold in US)
SAAB 900 Turbo $5,000 (Not really fussed about year)

AFAIK I'm well under (Probably at least $1/2 million) so this can go on any other classics that catch my eye or maybe some old bangers.

It would be grand to be so rich.