While certainly mp3s lose something, the biggest loss between the player and the ears is usually the headphones. Most mp3s now are fairly good quality (128 bitrate or over). iPod earbuds, however, are terrible, and are only suitable to be burned to appease the gods of music.

Spend $35 and get the cheapest acceptable headphones and you gain a tremendous amount. This is true even if you have some hearing loss in the highs (I have damage to my left ear) - the bass is better, separation is better, EVERYTHING is better. And that's with just a small step up.

You really have to be deaf to say that better audio equiptment is unneccessary - there are diminishing returns, but the step up from the bottom is a BIG step up, and even at the top there are differences.

Yeah, this is a valid point. You will still be saddled with whatever DAC you happen to have, but there is simply no cheaper way to go "audiophile" than a solid pair of headphones.

On that score, I cannot recommend the Grado Labs SR-60 model enough. They're unwieldy and ugly (I actually kind of like the sort of Bauhaus style they present, but most don't), and somewhat heavy, so you'll get plenty of laughs if you wear them while walking down the street, but they sound great and can be had for less than $70.

That said, they just aren't portable enough for me. Though I'm sure it undermines my "cred" with the audiophile set, I do actually own an iPod (or, more precisely, a pair of iPods) and use it all the time on my commute and while kicking around the neighborhood. I like the devices, a lot, and I'm not ashamed to admit it. However, the buds they come with are pure crap, and I broke them long ago anyway.

I could really use a new set of DURABLE, COMFORTABLE and PORTABLE earphones, ideally for less than $100. I'm having very little luck in this endeavor. Almost everything I've tried either (a) sounds like crap; (b) is intolerably uncomfortable (I tend to hate in-ear designs especially); or, (c) falls apart with a few months of use. I have probably bought six different pairs of headphones in the past two years. I'm stuck with a crappy-sounding pair of Sony clip-ons right now b/c they are the only ones rugged enough to take the punishment that train rides and storage in my desk drawer apparently dish out. I actually had one pair (Sonys as well, oddly enough...Fontopias) that simply disintegrated within 6 or 8 weeks. I can only guess it was because of human sweat, because I don't recall pouring any acid on them. In any event, I would LOVE to upgrade, and am even willing to dish out a fair amount, if it means that I'll have them for a while and not have to keep buying a new pair every few months. What are you using? If anyone has any suggestions, I would dearly LOVE to hear them.

I am currently using Koss PortaPros and before had Sennheiser PX100s. Neither of these have any isolation, though, so for loud areas you will hear things from outside (which is good and bad - you're less likely to get hit by a truck). I actually had two pairs of the Sennheisers, but they both died after a little over a year of my abuse. I haven't had the PortaPros long enough to tell you how rugged they are. One thing - the PortaPros are "distinctive" looking - some people think they're really ugly.

I've heard good things about the Grados and plan to upgrade to them when I have some money.

Grados are nice but not as comfortable as one would hope, and they are not sealed so they leak sound like crazy, not good for commuting. For full-sized sealed headphones I suggest Sony's MDR-V900HD. I've had a pair of MDR-V900's for about four years now. They are super-duper comfortable, very efficient (portable players drive them with ease) and are essentially a consumer-oriented clone of Sony's MDR-7509HD which are very popular for studio monitoring.

Grados still might be slightly better sounding than the V900/7509 Sony cans, but the Sonys are just so much more comfortable and discreet (sealed) that they are worth a good look. Don't pay more than $180 for the V900s, buy them from an online dealer... many big-name retailers (Guitar Center) sell the V900s at quite a markup... but also know that Guitar Center lets you negotiate the price of almost anything they sell. Do go try them out in person, if a pair of high-end full sized cans that will work with a portable is what you crave.

Thanks for the suggestions, guys, I will definitely take a look at the Sonys. I saw Amazon is selling them through a 3rd party for $170 or so, which I could stomach IF they are durable--I will pitch a major fit if they don't last at least a couple of years. I actually had a pair of PortaPros (they might have been "SportaPros", I honestly can't recall) some years ago when I was in school and remember kind of loving the sound quality but positively hating the fit and finish. Too bad, they are so cheap. I also had a pair of Sennheiser PMX100s, which must be related to the PX100s, and felt they were about the best of the lot I tried in the past couple of years, but unfortunately they broke about 5 or 6 months in. I guess I am just really rough with my earphones, which is strange b/c I have never broken a cell phone or iPod or Discman any other portable device.

I will vouch for the Sony V900 being durable, before I bought them I just assumed that headphones did not last, even expensive ones... and now I've had the Sonys for all this time, and I've actually abused them more than any headphone I've owned before.

It's true -- good headphones are the least expensive way to good audio.

I now use Shure c500s, which are a 2-driver design. They've now been discontinued and replaced by a 3-driver design, but they rock tight bass and awesome treble (I imagine the mid-range is even better with the 3-way).

They're in-ear sound-isolating phones that are great for loud, crowded places and flying on planes. The weakest when is the iPod's wimpy amplifier, but as Fred says in the article, when in public the convenience IS the quality. Some people may not like the "secret-service" look (the wires are snugged behind the ears, and the cord can be worn in back or front), but I love it. When used at work with a proper amplifier, they're feckin' wonderful. At home, though, I still like filling the room with my Gallo Ref. 3.1 speakers (no kids, and the dogs don't seem to mind).

I have Grado SR-80s (don't know how they compare to the SR-60s) and think they are great. Not that durable however -- I don't believe the construction is up to par with the sound quality.

I also have a pair of Sony Fontopia EX51 earbud headphones and they aren't too bad. I wanted decent, cheap ear canal headphones and these fit the bill. I've always had good luck with Sony headphones.

Try the (Seinhousser PXM 300) spelling, they are noise cancelling and simply amazing, I bought them cause my projector sounds like a screeming banshee, drives me nut. they were about $200 open box from Tiger Direct

I compare them sonically to the $600 Grado