When I first bought my Apple iPod, I suspected that I would not be able to tolerate the feeling of the included earbuds crammed into my ears, but I did not realize that they would fall out on their own. No, not because I typically get the cord caught on something and yank them out of my ear when I move my head, but because these ingenious devices tend to work their way out of my ear canals on their own because, contrary to the belief of the geniuses at Apple (they do call their tech support desk at the Apple Store the 'Genius Bar', right), one size does not fit all. Therefore, I had to go through several different "solutions" before arriving at one that works relatively well for me.

My first thought was to buy some headphones instead of earbuds. Although headphones do not sit as close to the eardrum as earbuds do, the iPod's built-in amplifier is powerful enough to drive headphones with an acceptable level of volume.

So, I set out to my local Circuit City to seek out a pair of headphones that would suit my needs. Please understand that I am not promoting Circuit City here. In fact, I hate the store, but since I had a gift card that I had been holding onto for close to a year, I figured that this would be a good excuse to get rid of it.

Upon my arrival at Circuit City, I stumbled around the isles until I found their very limited selection of headphones. Funny thing, but I would have expected to find them in an area near the stereo / home-theater equipment but they had been relegated to the same accessory aisle where you would find cell phone accessories.

After I started questioning "why would audio equipment go with cell phone accessories" it was clear that nobody understands the concept of "listening stations" that would help potential buyers determine what the headsets feel like, or maybe even more importantly, sound like. So, at this stage, it becomes nothing more than a guessing game based on brand recognition, trying to decipher the miniscule amount of information printed on the package, and guessing what the rest of the unit concealed in the plastic packaging was supposed to look like.

My first headset purchase was that of a pair of Sony headphones that were relatively small and light. I was hopeful that the amplifier in the iPod would be powerful enough to draw these headphones because I really didn't want a heavy contraption over my head if I could get decent sound out of something small and light. After all, the earbuds included with the iPod are tiny and they sound relatively decent, so why shouldn't a step up provide something similar?

After I purchased these headphones and took them home so I could get out a machete to cut through the awful plastic packaging that I couldn't open in the parking lot (okay, so I used scissors instead of a machete, but you get the point), I plugged them into my iPod and started listening. It wasn't long before I realized that it did not matter whether or not I was listening to Rock, Classical or Pop, these headphones were downright "tinny" and produced little to no bass response and let in so much outside noise that listening to them would be impractical and a huge disappointment.

The next day I went back to Circuit City and returned these lousy little headphones for store credit (remember, gift card as opposed to cash so I could then hunt for a real audio enthusiasts shop) and returned to the accessory aisle to take another stab at finding a set of headphones that would suffice.

In looking at my relatively puny range of choices in the price category (under $50.00), I had narrowed it down to two models, one by Sony and one by a company that I had never heard of, Nexxtech. Since the previous headphones had been since a major disappointment, and since I believe Sony has been more of a brand-name marketing machine for quite a few years now, I decided to take a chance on the Nexxtech model for $35.00. Again, after dealing with the removal of the plastic sheath that encased the headphones, I set out to determine what my listening experience would be.

I was relatively pleased by the sound of this pair of headphones and decided that I'd hang onto them even though they were a bit bulkier and heavier than I had originally sought out. I figured that you had to trade comfort for sound quality and just put up with the bar over my head and these heavily padded phones sitting directly on my ears.

Now that I found something that sounded relatively good, I soon realized the discomfort that would occur with long spans of listening. No, not the feeling of my eardrums bleeding in pain from the loud volume and good bass response, but from the discomfort of the heavy phones sitting on my tender ears. Not only that, but I was still frequently getting the cord caught on things. Although these things were not ripped from my ears the way earbuds were, the discomfort of the bar running over my head between the two phones was a bit unpleasant.

After about 6 months or so of this ritual, the cord had weakened enough that the right speaker kept cutting in and out, creating a rather annoying listening experience. So, I was back to trying to figure out the right approach to headphones. Since the wires seemed to be a common theme of annoyances and something that went over the ears provided for better sound but was somewhat uncomfortable, I decided that it was time to go wireless with a light-weight headset that would go over the ears.

Since the technology for many wireless headsets utilized infrared technology with a base unit that had to be plugged into a wall, my options for wireless were shrunk down to the newly evolving Bluetooth headset market. Since the iPod does not have a Bluetooth transmitter built in, it was further reduced to a headset that came with a device that plugged into the iPod and gave it Bluetooth functionality. After some serious issues in getting my hands on one, I opted to go with the IOGear Bluetooth headset (Model: GBIPODKIT). This device comes with a detachable microphone boom that connects to the headphones and gives you the option to pair the device with your cell phone and take calls, interrupting your music stream. It sure seemed like a pretty cool concept to me - pair the device with your iPod and your cell phone and you won't miss calls because of your music blocking out the ring tone. Also, you can pair the device with your computer for gaming and teleconferences via Skype and similar services.

After I charged up the headset, I plugged in the Bluetooth transmitter into my iPod and paired the devices. I put on the headset and found it to be rather comfortable; It was light weight and was attached behind the neck (check this) rather than over the head, which proved to be a bit more comfortable in the long term than listening with the Nexxtech headphones. However, I found that the Bluetooth transmitter did not have the type of range that I would expect based on my experience with my Plantronics Bluetooth headset I use for my phone. The signal was fine if the iPod was clipped to my pocket or on the table next to me while having my morning coffee, but walking 7 feet from my iPod to the refrigerator caused a major lapse in the signal compared to the 15 or so feet I get when walking away from my phone. Additionally, the volume wasn't very loud in comparison to my previous headset and the bass response was downright nonexistent. These headphones clearly wouldn't cut it for me as a music device, but are sufficient for things like voiceovers for video editing (remember the microphone boom add-on) and Skype calls.

For the time being, I reverted back to my $35.00 pain-inducing headphones and dealt with their downside while I did a little reading on reviews by my favorite computer geeks at MaximumPC.  In comparing the types of devices they were reviewing with what I was hoping for, it was obvious that I would need to go back to a corded headset as Bluetooth devices just weren't cutting it for audio quality. Additionally, I had already ruled out earbud and on-the-ear style headphones due to their inherent discomfort, so I set out to find me a pair of around-the-ear headphones that would give the exterior of my ears a rest. They spoke very highly of Sennheiser's offerings and I sought them out when I was at the Consumer Electronics Show to take a listen (since listening stations seem to be something of the past in retail establishments). I found their line of headphones to be very comfortable and sounded quite good (well, as good as you could expect with the outside noise of thousands of people talking to each other and adjacent vendors trying to get your attention with their high-volume displays.

It didn't take me long to realize that I would be paying a much higher price tag for these babies since they were of such high quality and are considered a high-end product, so I resigned myself to accept spending somewhere in the neighborhood of $200.00 for my next pair of headphones. Fortunately, it was January and I had just received a number of gift cards for Best Buy and was hopeful in finding they carried these as well. Unfortunately, the sales people at Best Buy never heard of this brand; my guess was that their Magnolia Audio/Video division would have, but for some reason even though they are part of the same company, I was told that you cannot use Best Buy gift cards in the Magnolia stores. In looking at the higher end headphones that Best Buy carried, they had a model by Shure (a well respected manufacturer of audio equipment) and a model by Bose (another well respected brand). Of these two, they actually had a pseudo-listening station setup to demo the Bose. I say "pseudo" because the listening station did not function, but at least I could put the headphones on and stand there for a while to see how they'd feel, which is a big step above what I had been dealing with in the past.

The Bose Triport headphones cost $139.00 and felt very comfortable considering their over-the-head headband design. They were lightweight, well padded, and overall comfortable, so I bought them with high hopes. I could have easily spent up to $200.00 here since I had more than that in total gift-card credit that I could use, but since this was the highest-end headset they carried, I'll wait until something else strikes my fancy to spend the remaining gift card balance.

When I got home, before I even opened the package, I decided to see if I could find a review of these headphones. One respectable-looking site gave the headphones only a 7 out of 10 rating, stating that one of the reasons for the lower score was durability. However, they also said that if they physically broke, Bose had no trouble repairing or replacing the headphones under warranty. Since I'm not very abusive with headphones (other than at volume level and my inherent ability to use the cord as a fishing hook), I didn't feel that this would be a major issue.

The other thing that the review said was that the bass response "could be better" and said that if you wanted better, you should buy the Sennheiser model HD590 that costs twice as much.  Based on this, I could tell that they had a good concept of what a good headset sounded like. Since I had 30 days to try these Bose headphones for myself with the option to return them for a full refund, I decided to take a chance and open the horrible packaging that we've all come to expect these days and plugged them into my iPod. After a week of listening, I felt that these were definitely the most comfortable headphones that I had ever worn and that the sound was crisp enough that you could hear the rosin across the bow on stringed instruments, the "plink" of plucking of a guitar, the drag of a brush across a snare drum and the nuances of a triangle. I admit that the reviewer was correct that the bass could be a bit better, as these headphones probably wouldn't cut it for genres such as house-music, hip-hop, rap, etc., but then again, I'm not listening to that stuff - I like "music", not "crap". I found that changing the settings of my iPod's built in EQ compensated for much of the reduced bass response.

Although I thought I could be happy with these headphones, I couldn't get over the fact that the bass response was a bit "phony" with the EQ settings and still didn't sound tight enough on certain types of music.  So, once again, I returned these headphones and went back to suffering with the torture devices known as the Nexxtech headphones.

One day I was speaking with my neighbor, who is an audio nut, and he actually had a pair of the Sennheiser HD590s that he offered to loan me to audition.  I could definitely understand why the reviewers of the Bose product gave this pair such high marks, but one thing I found that just didn't work well for me was the fact that it let in all of the outside noise.  This isn't a problem if you're sitting in a quiet room and try to submerse yourself into the music, but it is a problem if you're trying to mow the lawn while listening to your tunes.  So, it was evident to me that no matter how nice these sounded, they weren't the right headphones for me.

About a week later, I went to an event and was talking with a friend who worked for JBL/ Harman about my situation.  Her boyfriend, who also worked for the company, was telling me about a new product coming out that he thought might meet my requirements.  He offered to get me a "demo" model to try out and brought them to me at the next event we'd see each other at.  When I asked him if he was going to get me the employee discount on them if I liked them, he told me that it wasn't necessary because I got to keep these "demo" headphones free of charge.

These headphones were released under the name "JBL Reference 420" and is a relatively nice set of headphones.  Although not as comfortable as the Bose and not as precise as the Sennheiser models, they sound pretty decent and are a heck of a lot more comfortable than the Nexxtech unit that I kept going back and forth to.  Again, the bass isn't what I'd expect, but at least I've taken a step or two up from the Nexxtech unit and it didn't cost me anything but time and frustration.