I have to disagree with some of what's been said. I drove both (along with a '99 996) and decided to buy the TT. I liked the 996 best, but to be in my price range it had to have ~60 K miles on the odometer. The Boxster was nimble and the gearbox was amazing, but it definitely did not have the level of options the TT had for the price. The TT feels a little heavier than the Boxster, but it is loaded for the price. I've never regretted my TT, except on long trips since I'm 6 ft. tall. What the Audi has going for it that the Porsches don't is value. You get a turbo 225hp I-4, AWD, heated seats, 6 disc, more aft storage, and a better interior (in my opinion) for roughly the same price as a less-well-equipped Boxster. The newer TT and TT S are amazing and have even more power. While you sacrifice a little speed, you gain in handling with the AWD. Okay, I'm done with my sales pitch. I think I will go for a larger Audi next time, the wife and I are ready for a sedan. I wonder if an A8L is enough of a sedan for her.