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If you want to have a car that everybody and their mother drives, waste your money on a new 3-series. As for Benz's, you have to figure that they require a LOT of $ down and $ to maintain, so that seems out of the question.
Consider a used Inifiti Q45, Lexus LS 430, BMW 7-series (or even a brand new fully loaded Nissan Maxima).
They are all flagship/top-of-the-line models for their respective companies, very pimp indeed, and if you get one that's at least 2-3 years old, it will be super affordable because of all the depreciation. It's also much more fun driving a top of the line car from a luxury car company than it is to drive a low-end model from an ultra-luxury company.
Good luck on your car pimping endeavors.
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