Holy shit.  No one on this expansive interweb has done a decent job of telling a typical sports enthusiast what headphones will actually work during their activity.  Here is a breakdown of my 2007-2009 experience with musical workouts:

Let’s start with the worst, most frustrating design:

• The cord is approximately 16 feet too long.
• The cord is made of a super-grippy material, perhaps Formula-1 tire rubber, that grabs your neck when you turn your head to the side, causing anger, strangulation, and the opposing bud to be painfully yanked out of your ear.
• How the “twist-to-fit” design was conceived:  three German engineers took a trip to Amsterdam, and proceeded to take mind-altering drugs, listen to electronica, and then sit down to discuss a headphone design.  Since they couldn’t feel any pain in their state, they never realized that wedging something into your earlobe isn’t at all comfortable.
• If you need to remove them for any reason, you will have to fumble for 15 seconds to find the earbud, orient it, and awkwardly wedge it into your ear (this is a common theme with sports headphones designed without a semi-rigid behind-the-neck connecting piece).

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Sony Walkman NW202:

Sony almost designed the perfect active mp3 player with these.  Keyword: “Almost.”

The good:

• Great sound quality
• 2gig capacity was plenty for a “shuffle” style mp3 player.
• Great battery life
• Lightweight
• Drag-and-drop functionality
• Intuitive controls
• Reasonable noise isolation
• They stay in your ears while hanging upside-down on a climb, or falling from a 6-foot dyno.
• You can yank them off and they conveniently hang on your neck.
• They are easy to put back on if you need to have a conversation with someone.
• Different size silicone buds make them universally-wearable, even by freaks with huge ear holes, or tiny lobes.
• Cheap!

The bad:

• You look like Frankenstein while you are wearing them, or as if you are an über-bluetooth user.  This was acceptable since I thought I had finally found the perfect mp3 player, until………….
• YOU SWEAT ON THEM AND THEY STOP WORKING.  Honestly, Sony, did you test this product at all?  I mean, every review online said the exact same thing.  They all break if you sweat on them.  What did you think people were going to use an ultra-portable, headphone-mp3 player for?  Even funnier was that when my sweat first seeped through the enclosure and shorted something out, the rapid volume increase almost caused my head to explode.  If Sony re-designed these to be more water/sweat-resistant, I’d spend a ton of money on them, because they were otherwise perfect.

Sony MDR-AS40EX:

When these were my utility headphones, I wasn’t climbing, so I can’t comment on their effectiveness for my favorite sport.  However, I put them through the wringer otherwise.

• Pretty stable under heavy use.
• “Hangers” hold onto your ears pretty well, or at least offer the buds a bit of extra support.
• Cord extension allows for handheld music player operation, or armband attachment.
• Collar clip keeps the cord out of the way, so it doesn’t suffer the same problems as the Sennheiser phones
• Good sound quality (if you are using a properly-sized earbud) and sound isolation.

The bad:

• They will find their way out of your ear once you begin to sweat.
• If you want to have a conversation with someone, they just hang around your neck, and you can’t put them back in on the fly.
• People on the website have stated that they suffer the same sweat-induced malfunctioning as the walkman, i.e. they stop working if you sweat on them.  While I never encountered this problem, I’ll take them at their word.

• Totally stable, even for intense climbing/bouldering sessions.
• Good noise isolation
• Good sound, despite poor reviews on Sony’s website.  I seriously think that those people had a pound of wax in their ears, or had the wrong size earbud attachment on.
• The behind-the-neck connector was the perfect blend of rigidity, flexibility, and light weight.
• The behind-the-neck connector also served the purpose of routing the cord with a small adjuster, a genius little feature.
• They were easy to put on and take off to converse with friends.
• Had the same cord extension for wherever you wanted to wear your mp3 player (standard with active-style Sony headphones).
• Reasonable price.
• I like them.
• I miss them.

The bad:

• I feel silly mentioning this, but if you abuse them, the little plastic that connects the earbud to the main structure of the headphones will break.  I guess they could use some more reinforcement there, but they also include a carrying case that was of a convenient design.  If you have the small amount of discipline required to use that when you stow them away, this shouldn’t be an issue.
• People may have realized that these are the ideal headphones, and they like to steal them.

The verdict:

The Sony MDR-AS50G headphones are perfectly-designed for active use (…except for swimming.  Water sports can be handled by H2O Audio).  Don’t bother purchasing anything else. Thank me later after enjoying your favorite Mylie Cyrus tune while bouncing down the path to your local crag.