While not the five worst in absolute terms, these are some of the gears which I had lots of expectations for but in the end turned out to be overhyped upon actual listening.
Caveat: I personally favor a well-amped HD800 over anything electrostatic. The best electrostatic headphone system I've owned was a BHSE/SR-007 MK1--yes, I prefer SR-007 MK1 to SR-009--but even that got me bored eventually so they had to go.
1. Woo Audio WES
This was undoubtedly the most regrettable purchase during my journey as a headphile. I had it paired with my SR-009 at the time, only to my utter disappointment. Made me wonder if I had been cheated into buying a faulty unit. Later I got to hear another WES at a meet, and it sounded as awful as the one I had. The BHSE which I purchased later was a much better amp in every way, albeit at the same price.
2. Sennheiser Orpheus
I had very high expectations for this system, considering its legendary status among headphiles, so I was very excited when I got to hear it for the first time several years ago at an exhibition. While it wasn't bad per se, I thought to myself 'this is the sound of a so-called legendary system?' I understand some folks who like their music to sound romantic may enjoy the Orpheus a lot more than I did, but it just wasn't for me. The BHSE/SR-007 Mk1 was superior.
3. Ultrasone Edition 5
I was never a fan of Ultrasone. Shamelessly overpriced POS is what I would call them at best. However, seeing the price tag of $5K on the Edition 5, they must sound at least good, right? I mean, price ain't everything but it was even more expensive than the Abyss or SR-009. But heck no, it sounded horrendously metallic as most Ultrasones are and I would take a sub-$500 HD600 or HD650 over it any day.
4. Audeze EL-8, both open and closed
I heard both open and closed back versions, and they all turned out to be POS. Among all Audeze headphones I've owned/listened to, I personally liked my very first Audeze headphone--LCD-2 Rev.2--the best. F'ck me, right?
5. AK240/JH Layla
The AK240/JH Layla, which I believe costs over $4000, was the single most overpriced portable setup I've had the misery of listening to. Call me crazy, but I actually preferred my RWA-modded AK100 driving JH13 Pro FP over this combo for only about half the price.
While a bit off-topic, the following are my personal "leaderboard."
1. HD800 (best with ecp L-2)
2. SR-007 MK1 (best with HeadAmp BHSE)
3. HD600/650 (best with EC ZDSE)
4. JH13 Pro Freqphase
5. Sonic Frontiers SFD-2 MKII, SE+ modded by pcX --> the single best DAC I've heard, bar none. Stomps MSB Analog/Master 7/Metrum Hex/Bricasti M1/PWD2 with unmatched resolving power to detect even the tiniest microdynamic planktons while capturing the macrodynamics that just blew me away. While I'm not sure how it would hold its own when faced against the Yggy, but I'm confident it won't be a slouch.
