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I prefer the HD280's but it could just be because they are new to me and bring a new perspective and frankly, they're more comfortable. I'm probably able to give music my full attention while driving, in the same way you are able to on the train. When I drive it tends to be easy-going freeway driving and not much thought is needed. That said, I'm also able to treat music like a soundtrack to my life. I LOVE doing that, like I said in airports or new cities, it's a blast. my favorite music listening experience ever was with a crappy pair of stock iPod earbuds.