Very interesting thread. I couldn't help but notice many of you listen to hp's as to not disturb others. I mostly listen to them because I'm otherwise disturbed by other's noise. I'm highly noise sensitive, yet also deeply love music, so hp's is an obvious choice for me in such situations where I'd otherwise be bothered by noise.
I wear them at work when I'm not working on any audio (I'm a video producer), at home when our pets (or my wife) are making noise, and always when cutting grass.
Like a couple of you said, another benefit is listening to anything you want, no matter how weird, and not having to explain yourself to anybody. I also like the more musical detail and stereo imaging/centered sound stage no matter where I'm listening.
However, there are some negatives for me, too, which is why I can't say I prefer headphones over speakers. These are not being able to hear anything else so people can sneak up on me, or my wife can get frustrated by yelling at me and I never hear her with hp's on. I also don't like being thethered to something, especially if I'm trying to work on something physical. However, with the ipod and light ear buds of these times, this is a lot better than it used to be. In the 1970's, I owned a pair of big Sansui's where I about "had" to lay down to use them because they were so heavy! I now own a few pairs I can be comfortable wearing for long periods of time, although compared to many posts I've read here, it's not "that" long, anywhere from 2 to 4 hours would normally be a long time for me.
When I'm home alone, I never wear hp's but use my speakers. btw, my main speakers are giant vintage Pioneers w/15" woofers I have placed on either side right next to my desk as I'm at my desk most of the time.
So, I can't say I'd choose hp's over my speakers, but at times, I would, like right now because the bird is chirping, dog is yelping, wife is yelling at him and the TV is blaring!