I have a Route 66 (the original with 'regular' footswitches, not the big round ones). Never have run it direct, what did you use to "load it"- a DI box? The reason that I ask this is because Visual Sound pedals are designed with an output buffer to "see" an amp's input as its' load. Also, was the distortion or the compression the issue? There are several mitigating variables here...

You know I wasn't really watching exactly, I had him in and was mostly trying to get a sim amp for the session reverb, tone and let him fool around with the settings himself, I was answering the phone for part of this and recorded the whole thing. All other parts of the recording sound great. I played it back and the tone of the overdrive (but I'm thinking compression & overdrive) just sounded like sh&% to me. Yes he was DI into the Presonus instrument level preamp channel, he is also (active) Radial DI'd before the pedals for recording, potentially re-amping. I had started out with him Radial DI after the pedals but was not liking the sound enough so I figured I'd DI the guitar alone and then send it on to the pedals. Feed the pedal board to the Presonus in another channel for the monitor/headphone mix so he has his "sound". I attended, very briefly, a practice the band was having and I do remember him doing the song in question and not noticing that I was offended by that pedal's use. That is why I was thinking the amp load might be the issue.

Yeah, I think that may be the case. He may be able to simply re-adjust the tone of the OD section on the 66. It's probably too "gritty" or "fizzy", rolling down the Tone control may help reducing that top end trash. It would really be best to let him run through the amp, that acts like a giant "filter"...

Yeah, good ideas, when we record his parts definitely going for the miced amp so it shouldn't matter, but you identified exactly the sound, way, way too fizzy.