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[Kim]

@ Kim, are you using an audio interface? If so, doesn't that have a headphone out?

I have two computers.  One is a Mac Mini and the other is a Windows-based custom tower.  Both have the typical 1/8" speaker/headphone and Input jacks on the back.  I don't use USB for any of this at this time.  The active monitors are plugged into whichever pc I'm using and then when I use the cans, they are pugged right into the Headphone jack on the front of one of the monitors. 

[van Sinn]

So you're routing distorted signals through two different PC interfaces.
Which audio chips are used?  The Mac Mini has a fairly good Intel converter/codec (had one a few years ago), but what's in the PC?

Do you know how the headphone driver in the Alesis speakers is implemented?
It's quite possible that, while the build-in amp is ok, the headphone amp could be a simple  opamp..
My experiences with my DT770 vs the old Denon AH-D300 is that the Denon is a lot easier to drive than the DT770, even this is just the 80 Ohm version.

Another maybe issue could be that the Alesis monitors could be slightly rounding-off on the tone, and when you ten plug the more linear DT770 into an opamp-based headphone amp (assuming it is so made), you'll end up with a somewhat different tonal balance.
Suggestion: If you have access to a set of those inexpensive Sony earplugs I mentioned, do give it a try.
Ahh, the model is printed on the plug: MDR-2808.  Give 'em a spin!

[Harley Hexxe]

@ Kim, are you using an audio interface? If so, doesn't that have a headphone out?

I have two computers.  One is a Mac Mini and the other is a Windows-based custom tower.  Both have the typical 1/8" speaker/headphone and Input jacks on the back.  I don't use USB for any of this at this time.  The active monitors are plugged into whichever pc I'm using and then when I use the cans, they are pugged right into the Headphone jack on the front of one of the monitors.

  Wow, I thought my setup was complicated. What kind of interface connects your audio signal to your DAW then, MIDI?

[Kim]

Wow, I thought my setup was complicated. What kind of interface connects your audio signal to your DAW then, MIDI?

I think you might be overthinking this.  A bit.   

Direct recording/playing:
2 Quad Tube 1/4" Record Outs > (L & R TS 1/4" In) breakout box (TRS 1/8" Out) > Mac Input or tower pc Input.
Then when I use mic(s) I have an inexpensive ART tube mic preamp to interface one of the mics to the tower pc.  I don't bother with the Mac at that point because I won't get the mics out for just a practice or writing.  The Mac gets used for practice/writing/composing/iTunes and then all my normal internet stuff.  The tower pc is only for music recording/mixing/editing etc. and never on the net.

[rnolan]

Hey Kim, cool you've answered my question, all your A/D and D/A is done in the on board audio chips (mac and pc).  While these have got quite a bit better over time, you can still do allot better with a decent external (USB) audio interface (or descent PC sound card) and you get a midi interface (depending on gadget but is common).  There are a plethora of them available, eg the one Harley was looking at is a very good one.  Most of them come with some software bundled (quebase, protools etc albeit sometimes cut back versions).  Up side is these are dedicated devices and don't need to compete (as the on board chip sets do) for machine resources (well not in the same way). And they generally come with a decent headphone out.  Eg A simple Yamaha 2 in/out are not very expensive (comes with quebase IIRC). IMO something like this would be a very worthwhile addition to your setup and not a huge spend.  You can then run both your monitors (the Alesis are pretty flat and reasonable IIRC) and your headphones as required. And use the midi interface for MP2 editor program etc, or a keyboard, or change effects and patches on the fly...

[MarshallJMP]

Well I have to agree with R, usually those onboard soundcards are bad sounding.I never use them, even on my work PC I have an external soundcard for my headphones.
It's and old M audio card but it sounds a lot better then the build in card.