I would also support Edwood's comments about source and cans...particularly source. I would spend probably two to three times on my source what I spend on my amp and cans combined.
As for the amps...I think it depends on whether they are tube or solid state, as they have significantly different sonic signatures.
TUBE:
Moth Audio 2A3SiH - This would be Nightfall's amp, and it's a damn fine one. Not only does is sound great, but it's a good looking amp too.
ASL Twinhead Prototype - This would be Jude's famous "ringer" amp, which has since departed this earth (or at least around Detroit). I heard it for the first time at a meet, hooked up to a Wadia 861, and all I could say was WOW!!
Ray Samuels Emmeline II (The Raptor) - Ray has done something here in which he should take great pride. This is a sweet sounding amp with nice detail and well-controlled bass. It really takes some of the best features of tube and solid state amps. I've heard it a couple of times now, the last listen at a recent Detroit meet with an SACD-Mods Sony 555, and I've been more impressed each time. A very nice amp!
SOLID STATE:
HeadRoom Max w/ 2004 Reference Module and Stepped Attenuator - This is how music ought to be done in Solid State. It's sweet, detailed, with nice punchy bass...but they really get the midrange right on this one. It's one of those amps that just disappears when you listen to it...all you hear is the music. I happen to think that it's got a lot to do with the crossfeed...but that's my opinion.
Ray Samuels Emmeline HR-2 - Dead quiet, with nice detail...yet the highs don't sound harsh. Paired with the AKG K501 or Sennheiser HD-600 it will knock your socks off.
Meier Corda PreHead - That it includes preamp functionality makes it a very nice buy.
I also make a special mention of chosen1's Uber-PPA, which is without a doubt the finest DIY amp I've heard. He has made something very special here.