Well, you can usually get Sennheiser HD580s for less than that on EBay. They're amazingly good headphones. They're "circumaural", meaning they go completely over your ears, and are so incredibly comfortable that you can literally forget you have them on. They're 'open', meaning that outside sound still gets in and your music leaks out, which can be a problem under some circumstances. Closed headphones don't leak sound, but are almost always less comfortable.

The only real drawback to the Senns is that they're a high-resistance load, 300 ohms. That means they need a headphone amp (or a device with a high-powered port, which is unusual) to reach their full potential. They sound good 'naked'; my iPod is able to drive them very nicely. But if you have good quality sources, they'll benefit from an amp. The sound opens up and goes from 'great' to "holy crap, I can't believe how good that sounds!"

If you're into music, most computer soundcards do not put out a good quality signal. Finding a really good source is a pain in the ass. One solution is the very cheap Chaintech AV-710, which is about $20 on Newegg. You can drive this card in ASIO or kernel streaming mode using the included drivers. It sucks, horribly, for gaming, but it's a good music card. (you can have more than one soundcard in the system...you just tell Windows to use the other one by default and point your music players at the Chaintech.) I haven't tested, as I use my 710 to drive a receiver, but rumor claims that the channel 7&8 DAC chip is the best on the 710. It's widely claimed you'll get the best sound by plugging into that port. (and telling Winamp or Foobar to play on those channels.)

Another option is the Bithead from Headroom; it's a little headphone amp and stereo DAC, all in one. It can draw power from USB or from batteries. (batteries are better.) The major downside? These are expensive little units. They'll blow your whole budget just by themselves. So you'd probably add one later. (you can find them over here.) This is, however, a nearly perfect solution; it includes everything you need for dynamite sound with little to no fuss.

If you're at all handy with a soldering iron, one of my Make magazines has a project to build a headphone amp into an Altoids tin. I think the parts are about $30, but if you don't have any tools, you'd probably end up spending $75 or so. If you're interested in that route, I can forward you the info on how to build one.

The other major names in extremely high quality headphones are Grado, Stax, and Beyerdynamic. I'm not too familiar with Stax and Beyer, because they were so much more expensive than the Senns were when I was buying. The Grados have a rep of deeper bass. Their sound is reputed to be a little 'colored' toward the low end; they're better suited to bass-heavy music. Many people find them a bit uncomfortable. They're sealed headphones, too, which could be an important feature for you. In the Grado line, you'd probably want to look at the SR-60 or SR-80. The $60 is a $70ish headphone, and doesn't need an amp. The 80 is about $100, and DOES need an amp to sound its best. I don't think either is going to be as good as the Senn 580s, but they're substantially cheaper.

I'll let other folks comment on Stax and Beyer, as I have no experience with them at all. The brands I have exposure to are Sony, Bose, and Sennheiser, and the 580/600/650s just absolutely destroy anything I've heard from those other makers.

A good alternative to the HD580's would be the HD595's. The don't have the crazy high resistance the 580's do (50 ohms versus 300) so they're a lot easier to drive with something like an mp3 player. The sound on the 595's is a teensy bit brighter than the 580's and it has a more "open" or "airy" sound but they still have that usual Sennheiser warmth to them. They won't have quite the bass response that the 580's do (or even a set of 280 pro's) but they'll still blow away any set of headphones you get at a consumer electronics store. Great pair of phones for just about everything. They've been referred to before as "Jack of all trades, master of none" by some and I'd say that's not a bad description nor is it a bad thing. They'll easily blow away your pair of Plantronics or probably any other pair of headphones you've bought but they won't excel at say.. classical music like the 580's do when paired with a decent amp. It's a question of what exactly you're after.

Pricing on the 595's is down to like $190 or so on Headphone.com. The 580's are maybe $5 more, but again I think to really get the most out of the 580's you kind of need an amp and that adds to your cost.

If you look into Beyerdynamic the DT770's ($250) are hugely popular with the gaming crowd and are supposedly really good for people that want a lot of bass. You break into the "kinda needs an amp" range here though too with an impedance rating of 250 ohms. I almost went with them as they're a sealed design so they block outside noise a lot better than either of the of Sennheisers. In the end though I just really wanted to save $50. Plus I knew getting the 770's would lead me to eventually purchase a new amp (I have a little "prosumer" level amp but it's just ok, nothing great) and I really just wasn't up for the extra dough.

You don't want any of the various "gaming" 5.1 sets, or any multi-driver sets really. Not even the set (Tritons?) that Rabbit recommended. Just trust me on this one. None of them have good frequency response on the low end. I've used two sets now and while one of the two sets I tried would probably sound like an improvement over your Plantronics phones they're still crap compared to even a middle of the road set of $100 Sennheiser or Beyerdynamic cans.

I'm still sticking with my recommendation on the 595's. I think they're the best multi-purpose set out right now in your given price range.

I also can't recommend Headroom (headphone.com) enough. You might be able to find whatever set of phones you decide on cheaper elsewhere if you look, but I've dealt with Headroom 4 or 5 times now and had really great experiences with them. I'll always spend an extra $15 or $20 to throw business their way over a big site like Amazon or wherever else. I had a problem with one order when I killed a credit card ($480 in spent in Mexico on the same day I made multiple purchases in Kentucky... yay for fraud!) and they called me about 25 minutes after I submitted the order to ask if I wanted to use a different card number or cancel or how I wanted to handle it. They were super helpful and still got my order out to Fedex that day, which was awesome as it was a Christmas gift. Again, I just cannot recommend them enough.

My takeaway here is that the 595's would be a good bet for now. If I feel I want more later, I'll bring them into work and get a new set plus amp for home. Both the 595s and 580s are just barely under my price-out range, and the reviews in general on both cans are very good. This would seem to catch me the potential best of both worlds?

The Triton AX 360s. They are phenomenal and have almost completely replaced my $800 surround system. The mic on them some have had issue with, but once you get it in the right place it's golden. They are not at all hard to set up, have optical and digital coax and are Dolby Digital certified. Buy them now.

Audiotechnica A900 or Beyerdynamic DT-770. The Audiotechnicas don't need an amp so if you're trying to stay near the $200 mark that's what I'd go with. Both produce much more boom to their bass then the Senns that have also been recommended, which can be a fault musically but works well for games and movies.

I use the old style 770-80 Pro's as my everyday music headphones, because I haven't found any headphones with better bass. I completely agree that their sound (and the A900's) is not for everyone, and even for me there are some kinds of music that just doesn't work well with them. But they are great overall cans in my book.

I would not get the current model 770's as long as the old ones are still easily available. If you happen to have a Guitar Center near you then you can try before you buy also, as they stock them. Even with the 80 ohm version though you will still need an amp to get them to sound right. If you're going unamped, the A900's are definitely better for music or games.

EDIT: I forgot to mention that the A900's have pleather ear cups, which is an immediate deal breaker for some people. They are very comfy but can give you the Ear Sweats if you are prone to that sort of thing.

Great info in this thread guys, I really appreciate it, and I'm sure lurkers in my boat do as well

I decided to go with the Senn 595s - they seem to be a good multi-tasker, and that's what I like. An EE I work with actually has two different pair at work - the Grado 225 and the Senn HD 580, and I got to try out. I wish he had a pair of the A900s but I was actually really happy with comfort of the Senns, so I decided to go with the similar 595s as I was leaning that way anyway. Plus, if I decide to upgrade with an amp they would make for good at-work headphones and I could get something else for home down the line.

Ah. The Head-Fi slogan

Yeah, after listening to a few different sets of headphones I have to say a lot of the stuff they buy sounds like placebo effect. I've managed to avoid most of their purchase-inspiring jargon so far. The proof is right here on my desk in a cheap little amp and one set of headphones. The other set I have travels around with my laptop.

Got the cans in the mail today, hooked them up the computer and I must say I am very impressed. The quality is fantastic, and they are very comfortable. This is hooked up to my ancient SB Live! as well - I want to stick them into my nicer AV Receiver in the living room and play some CDs later. Great pick guys

I do like my Tritton's but now I need to find a way to take the optical out of my 360 and get it into my regular speakers as well.

I find a good "burn in" improves the sound. With a new pair, I usually setup a diverse playlist and let it run all night. Let us know how comfortable they are after long listens. I find that to be one of the biggest problems with picking out headphones.

A question: why headphone amps seem to be so freaking expensive?

This is exactly what I meant. For a $300 or so, you can easily buy a full blown receiver. A 5.1 or even a 7.1 multichannel variety, brand name, with half a dozen outputs, multiple coax and optical inputs, not a snooty audiophile level, but certainly more than enough to cover 99% of a home theater scenarios. Go to a BestBuy, and chances are these same $300 will even get you a receiver + speakers bundle.

With these headphone amps, OTOH, $200 only begins to buy you a little piddly little box that boosts your stereo signal level. This is way whack. Or am I missing something?

Well the only thing I can think of right offhand is that most receivers aren't going to drive an expensive set of headphones to their full potential. You'd be surprised how many HT receivers put out just as little power on their headphone jack as your dinky mobile mp3 player does.

That said.. DS is completely right. Whether the cost is worth it to you or not is entirely relative and personal.