Honestly, if I was fresh out of school and had that kind of money to drop on something 'fun' and just had to spend it (instead of putting it towards a downpayment on a house or something boring and practical....) I'd buy a classic muscle car, enjoy it and then when the time came to buy something more practical, I'd sell it for the same amount or more than I paid to begin with. You won't do that with any 'modern' car. 1965 GTO would be my choice for a convertible (of course not a hard top, but I'm fairly certain I wouldn't care).
And it would go UP in value over time...just sayin'...