[MrPanda]

Telex 610's and Telex in general are up there. All the Aiwas that used to come with their walkman clones. 
The most recent headphone disaster I bought was around 2009 - an impulse buy of some Philips circumaurals from Best Buy that had really big ear cups ( I have big ears).  I brought them home thinking, "these are light and these are going to fit!"... well, they sounded like those little white transistor radio earpieces stuck in a 24 pack of Charmin crammed into a Kleenex box.   Absolutely no dynamic range, absolutely no clarity.  The driver sounded like it was being smothered in wet cotton balls.  I was looking for them last night to get the model number, but I remember now that I threw them away when the headband broke.  I kind wish I had the model number, in the same way you kind of want to remember the title of that bad horror movie who's name you can't place...

 

[noxa]

For me the worst not overall put for the price were the CKW1000ANV, i was expecting so much and was so dissapointed.

 

[AnalogSavior]

Worst phones I've used were probably some early 90s cheap, off brand on ear phones from a discount bin.

Phones that are objectively good but left me disappointed were Hifiman RE400 iem. So hyped at the price point, but I found them very flat, and a little boring. I preferred my Sony XBA-1 during an A-B test but then again, I like the balanced armature sound.

 

[Roboturner913]

New candidate, the 2XL Spoke. Made by Skullcandy. Not like I was expecting much but they were $3. Worst three dollars I have ever spent. EVER. I could've gone to Burger King and hit up the cheapie dollar menu and come away infinitely more satisfied. In fact, thinking about all the good and decent things I could've got for $3 makes me want to be sick. I could've gotten 2 two-liter Cherry Cokes, a few postage stamps, most of a gallon of gas, a gallon of milk, a roll of scotch tape, a 40 ounce Miller High Life, a box of Girl Scout cookies, a box of paper clips, a couple packs of Juicy Fruit, a cheap pair of socks, a bunch of those ponytail rubber bands my wife strews all over the house, a bargain bin vinyl from the used record store down the street, a few disposable razors or my kid's favorite episode of Yo Gabba Gabba from Amazon Prime. But nooooo, I just had to buy yet another pair of cheapo headphones that were predictably crap and which listening experience I can only compare to the time I disconnected the tweeters and midrange from some ancient Realistic speakers which had been sitting in my uncle's attic since the mid-70s and hooked them up to an Emerson boombox for use as "subwoofers". At least I had an excuse then - I was 12. What am I doing with my life? damn that was depressing. Time for another glass of scotch.

 

[cswann1]

.......a 40 ounce Miller High Life.......

 
 
Da'amn knee-grow!  Where you be gettin yo MHL?  Saks 5th Ave?  

 

[semaj8james]

  I could've gotten 2 two-liter Cherry Cokes, a few postage stamps, most of a gallon of gas, a gallon of milk, a roll of scotch tape, a 40 ounce Miller High Life, a box of Girl Scout cookies, a box of paper clips, a couple packs of Juicy Fruit, a cheap pair of socks, a bunch of those ponytail rubber bands my wife strews all over the house, a bargain bin vinyl from the used record store down the street, a few disposable razors

Where do you live where you can get all of those for $3??
And I must say, I'd prefer those items over 1 episode of yo-gabba gabba.

 

[ThickGlasses]

  Where do you live where you can get all of those for $3??
And I must say, I'd prefer those items over 1 episode of yo-gabba gabba.

Not all at once for $3.

 

[IEMagnet01]

$3 gets you cover charge at the most exclusive club in the city...The Fountainhead.

 

[Penta]

LG buds from a cellphone I bought on this christmas. It manages to be worse than a 3,5$ headphone I bought once.
Just tested it again on Ryan Farish's Songbird: It sounds like the music is coming from a tube and has no detail at all. The guitars sounds like they're coming from a kid's toy.

 

[ru57y]

 
Some of the higher end stuff is actually pretty loved around here, but if you were ever unfortunate enough to hear the $5 earbuds they make, you will be scarred for life.
 

yeah bro! I love my XBA-30's they seriously rock my socks when I'm out and about and am too scared I'll get mugged wearing my 650's. 
 
My pulse headset for gaming is ok for LOUD NOISES
 
BUT 
 
worst headphones - the POS $5 Sony pack in 'buds I got with my voice recorder. 
Not only did they grate at every frequency, they didn't even fit in properly. 
They have since been confined to my "Bag of crappy headphones I'll never use even in an emergency but if someone who doesn't care about their sanity needs a pair they can seriously just have them" along with my pack-in Samsung galaxy ones, my PS4 pack-in headset and my SE210's, cos they broke and were way too bassy. 

 

[DangerToast]

Anything turtle beach makes

 

[lin0003]

  yeah bro! I love my XBA-30's they seriously rock my socks when I'm out and about and am too scared I'll get mugged wearing my 650's. 
 
My pulse headset for gaming is ok for LOUD NOISES
 
BUT 
 
worst headphones - the POS $5 Sony pack in 'buds I got with my voice recorder. 
Not only did they grate at every frequency, they didn't even fit in properly. 
They have since been confined to my "Bag of crappy headphones I'll never use even in an emergency but if someone who doesn't care about their sanity needs a pair they can seriously just have them" along with my pack-in Samsung galaxy ones, my PS4 pack-in headset and my SE210's, cos they broke and were way too bassy. 

Lol seriously? You consider the SE210 to be one of the worst you've ever heard? I'll buy them off you if that is the case!

 

[ru57y]

  Lol seriously? You consider the SE210 to be one of the worst you've ever heard? I'll buy them off you if that is the case!

 
I treasured them hoping they would one day sound like heaven but the day never came and as such caused mucho bitterness. 
I found them way too muddy, ridiculously comfortable but the bass was overpowering and lacking in any oomph, seemed way too flat. Felt like I wasted my £70 back in 2008. Guess that's when I rediscovered Sennheiser! 
Trust me you don't want them, the cables were terrible, they literally split themselves open after a year. I resoldered them to some super high quality cable back in 2009 but they now live back in England in a box of stuff I really wish I'd tried out before dropping cash on, the rubber back bit of them has gone a weird colour and went uncomfortably hard and flaky. 
Maybe I got a crappy pair? 
they looked sci-fi as hell though. loved that. 
 
 
 
AND the 'phones I got with my Clip were pretty ghastly. Who uses them anyway?! 

 

[lin0003]

Lol. I tried them and they were decent. Better than the SE215s IMO. 

 

[pacman46]

Worst phones I've used were probably some early 90s cheap, off brand on ear phones from a discount bin.

Phones that are objectively good but left me disappointed were Hifiman RE400 iem. So hyped at the price point, but I found them very flat, and a little boring. I preferred my Sony XBA-1 during an A-B test but then again, I like the balanced armature sound.

sorry for the really late response.. But really? You think they are one of the worst? Of course everyone has different tastes.. I think that Specially for the price is a very nice phone.. I do agree that it's not a fun sounding iem.. In terms of like a v. Sounding earphones.. I think it sounds great.. Imo of course.. At first when I got it I was like.. Huh? Lol but when using it for a while.. Like most iems.. Or some anyways.. Takes a little time to adjust.. After using it for a while then taking it out and putting something else in.. That was like almost three times as much.. I was like no no put the re400 back in.. Lol I wouldn't have expected to see that phone on here lol but hey each their own rite... Again just my opinion... Happy listening..