[Arainach]

Grados with Bowls. Closely followed by Grados with anything else except C-Pads.

 

[craftech]

The most uncomfortable headphones I have ever worn were actually my first ones. The Superex ST-Pro B. They sounded great but were built like aviator headphones and could hold together two 4 x 8 sheets of 3/4" plywood for gluing.
My grandfather who liked classical music and opera was going deaf and was thrilled when he heard them.
He used to wear them for hours because he was a "maestro" who was frustrated at age 94 that he could no longer hear the music he loved. When he took the Superex headphones off he had red rings around his ears and a splitting headache, but he had a smile on his face.
Before he died I bought a pair of Audio Technica ATH-7 electret condenser headphones which are still amazing today. What a difference.

 

[kitaoji]

i'd say those clip on headphones Sony produced (Q55 or Q22 or something like that). The _clips_ hurt my ears, and then the sound would be pretty bad, since there was so much space between my ear canal & the speaker. Stopped after 5 mins. And I'm much happier sticking with earbuds & IEMs.

 

[DJGeorgeT]

super.fi 5 Pro and EB. They hurt my ear canals.

KSC-75. They feel like they are halfway hanging on my ears. It irritates me.

 

[CJ_CoCa]

Quote:

Originally Posted by kramer5150 Shure e2c... cant leave them in for more than 40 minutes. They tickle the little hairs in my ears and its very annoying. Especially while walking around. I never had this problem ~6 months ago, just more recently. Garrett

I agree.
Also, I've had my SR 225 for a week, and at first I could barely use them for an hour...I've been listening to them for about 3 hrs now...with bowls

 

[jagorev]

Most uncomfortable I've ever tried: Etymotic er-6i or er-4 with tri-flange tips. It was like ear-torture. Grados are nothing compared to Etys.

 

[coco]

I once had a pair of behind the head sonys, circa 1995 or so. I am not sure if they still make them. They are held in place with a clip thing that pinches the ear. It was the kind of pain that sort of creeps up on you. Feels fine for about 10 min, and then...damn, what is that burning sensation on my $#@$!! ear. Is someone putting out a cigarette on the crown of my ear?!! A special kind of pain. Good thing they sounded horrible.

 

[kencer]

Quote:

Originally Posted by CJC252 I think almost all behind-the-neck (or street style) headphones are really uncomfortable, because the weight of the cans are always digging into the top of the base of your ear. Plus, you can't really lean back on anything while you have them on.

i second that..bought one out of curiousity and realised i wasted my money.

AKG K-66, hurts my left ear lobe after 40 over minutes

 

[jjcha]

Hmm, I'm okay with Grado and the various IEM, but for me the most uncomfortable is easily the Senn HD25-1. Man such clamping superaural force! It did improve with stretching out and figuring out how to wear them, but man, these were easily the worst.

Best,

-Jason

 

[familyman]

alrighty, my vote is for the hd280 pro.

someone had to.

 

[spraggih]

AKG K26Ps - Small earphones with a harsh clamp. Wore them for about 5 minutes.

 

[Jahn]

IEMs. The whole damned dirty lot of 'em.

 

[NotJeffBuckley]

Quote:

Originally Posted by Jahn IEMs. The whole damned dirty lot of 'em.

You're right, these are far less comfortable than Grado headphones to me. However, I've recently found a brand of earplugs that is exceptionally comfortable, so I'm looking into IEMs that have a similar tip style.

 

[mjb]

Quote:

Originally Posted by Jahn IEMs. The whole damned dirty lot of 'em.

here here...ugh. in addition to the ear canal pain, the isolation/ear seal makes my stomach queasy.

 

[sxr71]

These SR-225s that arrived today hurt like crazy. I can barely tolerate them for 15 minutes. Even worse is that I really don't like how they sound with the bowls as they do with reversed bowls. The reversed bowls actually let the plastic contact your ears and they hurt in about 5 minutes.


All this aside I will admit that ER-4s with triflanges have in the past hurt to the point that I wanted to scream and curse. However. now with foamies I listen to them for 4-5 hours continuously with no problems.