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I've a huge head, too, and it's an issue that you should take seriously, both for his comfort and for the life of the headphones. So many headsets have broken on my head over the years through no fault of anything other than they are made to fit certain sizes of heads that don't include the larger ones!
With that in mind, I recommend these: Plantronics GameCom 367
That's the set I've used for gaming for years now. They're solid but light and comfortable on my huge head. "Years" is an important word, since I've spent hundreds and hundreds of dollars on 'nicer' headsets that last 6-9 months before one of the cups breaks off.
These have faithfully served me for at least two years... I would highly recommend them.
I had a Gamecom Headset On Amazon and it was decent. Problem was, the mic broke, so I lost a headset but gained a decent pair of headphones. I wouldn't recommend them though.
what i have is the Plantronics GameCom 367 Closed-Ear Gaming Headset -- they work pretty well (but the problem is that after wearing them for a couple of hours they start to hurt your ears a little...but thats only after a couple of hours)
I've had this for about a year now and I'm so happy with them I'll buy a new one when it eventually breaks. It's really sturdy, I've dropped it 50 times~, even sat on it a few times (and I'm quite heavy, 195lbs) and it's still up and kicking. The microphone is of good enough quality, works great on Source Games and Skype and other VOIP services, even though it's a little short. The sound quality is perfect, and while it's not the best by far, I really like the bass it kicks. It makes it easy to detect where other players are in FPS and games like that. The ear cup is quite large (which is good since I have big ears) and comfy, I've never had any problem with it. At first you'll need to get used to it because it's warm, but after a week of wearing them it'll be like a new pair of ears. The only downside is that it doesn't keep the sound in the ear cup. If I turn up the volume enough I can use it as a speaker
Im currently checking into some for myself was told to check these out.
Someone just recommended these.
They are both lower than your price range but I can recommend both of these:
[link] Plantronics headset. My roommate has this and it is awesome. Large and very comfortable - the sound really booms. The mic is undetectable when you fold it back into the headpiece itself - it does not look like a cheap headset at all.
I have used this headset in the past and really enjoyed it. It goes behind the head so you don't have to worry much about size, and every angle on the headset is adjustable so that you get a perfect fit. If you like things really loud there is some sound leakage that might bother the people around you but aside from that it is an awesome set. Good luck with your search!
I bought theGamecon 367 some years back when Circuit city was closing, they've been the best most comfortable headset that I've had.
I bought a pair of turtle beaches for my computer bag they fold nicely into the headset pouch on my bag after a year of light use they're falling apart and have rips in the cloth. I'll be looking into buying another pair of from plantronics.