Interesting. Didn't think that a headphone debate would occur from this, but.... Never tried the Sony MDR-A22, (Or have I? Read on.) but I've DJ'ed for years with a pair of Sony MDR-7506 Monitor full-cup headphones and loved the balance of highs and lows that they've brought out. 15 years ago I bought cheap a pair of Panasonic RP-HT710 headphones so that I could modify them with a condenser boom mic add on, and I've used them since, albeit I think that they sound way inferior to the Sony's and AKG's. I've tried the earbud phones, but never liked how they felt. Instead I've gone with headphone that actually came with walkmans in the 1980's and 90's. My 1st pair of portable headphones were a pair of 1982 Nova-25's. At that time the sound quality blew away anything else I had at that time. They also felt good to me. Now, as far as puting AKG K240's to an HF rig, that was a "what if". I like monitoring the AM HAM's on 3740KHz, 3885KHz, and 7295KHz, and actually do talk AM on 29.000MHz and 50.400MHz. The audio tonal quality with those AKG's on the Kenwood rig totally surprised me just how broadcast quality these dudes sounded. And if you have a good sounding music MW, or SW, station then the AKG's just bring out the natural quality of these broadcasts as well. I understand that Drake R8's sound super as well. And if you use these phones to listen to mono toned utility stations, they seem to bring out the full 300Hz - 2.5KHz that they only transmit well with great clarity. Now, as far as a recommendation to a decent pair of earbud headphones, I'm afraid that I'm the wrong one to ask of that since any earbuds that I do have are as new as 1995, and they may possibly be Radio Shack rip-off's of your Sony MDR-A22's that were on a clearance sale at the time. However, they look the same, and bare the Radio Shack name on them. I do remember that it was one of those better impulse buys that turned out to be a good one. Sorry I couldn't really answer your question.