Need Help buying headphones and head amps

My nephew is looking for quality headphones and a head amplifier for listening from his MAC computer. I know very little about headphones and head amps so I need some recommendations. After some research, I found the Sennheiser HD 650 Headphones and also the Grado GH1 headphones. The IFI - MICRO IDSD DAC also looks very interesting but I do no know. He will probably run a USB cable from the MAC to the head amp (any other suggestions?).

Does anyone have any suggestions for a high quality headphone and a head amplifier? Let’s assume a budget of $1,000 or less for both items. Any suggestions would be appreciated.

My plan is to give him 2-3 suggestions for each item and will then suggest he visit a dealer for listening and additional help. Where should he go in the downtown Chicago area for assistance? He needs a dealer that will help him make these decisions. Of course, purchasing items on line is also an option if someone suggests something. Thanks..
With a budget of $1000, you should be able to get something very good. The only problem is that there are so many choices, it can be overwhelming. I can give you 2 pretty good options. First, is The Cable Company. If you don't already know who they are, Cable Co's speciality is that they have a huge inventory of demo components to lend out. You can have them send you 3 or 4 pairs of headphones and amps to match, and you can try them all at once. They will give you good advice based on your needs, and not what they have in stock that needs to get moved. I've been doing business with them since the early 90's, and are one of the most reputable businesses I've ever dealt with. If you pick something that they don't have in stock, they'll let you keep the demo gear until it comes in. If you can't already tell, this would be my first choice.

You can also try Headroom. Web site is If anything, its a great resource. They have a huge inventory and a lot of user reviews from customers on their web site. I don't know them well enough to take advice from them, but they do have an excellent reputation and you can learn a lot on their web site.

If you already know what you want, you can try They're mostly known as an online company, but they are in Chicago and you can actually go there if you live locally. They're not a bad place to do business with, but they are a very high pressure sales oriented business. They try and sell you want they want you to buy.

With headphones, I like to try them first because the fit has to be right. So even if you read some good reviews, the ergonomics play a big part in the decision.
Sennheiser HD600 or HD650 with a Bottlehead Crack amp. Total investment is probably about $600. The only caveat is you have to build the headphone amp but to me that just makes it more fun.
Read it's what audiogon is just for headphone listening. Many smaller companies offer the best stuff. Many of the reviewers compare tons of items. The relatively lower costs results in many who build a collection and can compare in ways that we often can't here with high $ speakers, etc. Cheers,
Take a look at the Topping TP32ex. You can find them on Amazon. It has a
good Dac, USB input, plus a digital coax and analog input as well. It is not
only a headphone amp, but is also a 50 watt per side digital power amp to
drive speakers if so desired. I have it and it sounds great.