Hmmm... between the headphones I've owned, the Audio Technica ATH-W10VTG. Great looking headphones, but they are by far the funkiest sounding headphones I've owned.

Its not THAT bad, at least not till the price skyrocketed to its current retail. It was cheap and good at the time it was released.

I can only think of two off the top of my head that I felt were utterly wretched.

The original Beats Solo
- sucks like a two dolla tranny that's all fanny and nothin' else

Grado HF-1
- dear sweet jebus these make the 325 tame by comparison

Sure, it isn't THAT bad - actually it's better than most single opamp Cmoys. The legend around it was its main problem. Sold it to a friend of mine, who actually liked the sound through some Beyer cans.

Definitely the legend around it that's the problem. When I had my O2, I liked it. I was able to enjoy it because:

1. I understood that it was an entry-level semi-portable amplifier;
2. It sounded better than a FiiO E11 or the amp section of an Audioengine D1.

I wasn't exposed to the rabid, Heaven's Gate-like fanaticism surrounding the O2 until after I had already *heard* how much better other better amplifiers sounded. As a result I knew that all of the "audibly transparent" talk was a bunch of nonsense. Add that to the very low expectations created by other entry level products available at the time, and it means I can look back with a little nostalgic fondness for the Harsh Sounding Amp That Could.


My own expectation-based pick: fuck the Sennheiser Momentum. I was so excited about that headphone because of its sexy looks and great materials...and when I put it on I was like, "Where's the treble? Do these things just *stop* at 7k? How are the mids that far back?" My ears even fit inside the pads, albeit with no room to breathe. I know rationally that the Momentum isn't that bad of a headphone. It's certainly not one of the worst headphones that I've ever heard. But the lizard brain still loathes what it loathes. 

This is a toughie. I've had some pretty bad experiences. This will be a mix of just bad and really terribly missed expectations:

PHA-1 - My unit that Marv and CT hated . I asked for a specific DAC from a buddy coming back from Japan and he was convinced by the shop owner to buy this instead...

Beats Solo 1 - First time I heard them I started laughing out loud at my buddy who had purchased them.

Leben CS300 xs - Probably the worst purchase I've made in my life. It's like someone poured Karo syrup on my sound

Goldenear Triton 2 - My buddy's father co-founded the company with Sandy Gross and offered me dealer pricing. I was so excited until I went to audition them and shut my mouth. They were worse than Energy RC-70s paired with a shitty Klipsch sub for both HT and music. This was also when I got to demo a pair of Philharmonic 3s and (secretly) fell in love with Dennis Murphy. The contrast between the two was pretty stark.

Dying LCD3 - when my pair was on it's last legs it made all music sound like it was being reproduced by a donkey's rear end.

BONUS:

Senn HD700 - Having owned the 580, 600, 650, and 800 at various times, I figured the 700 would be right up my alley. I figured wrong.