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Getting good quality guitar sound

Hello, i have been having trouble getting a good quality sound when i record an electric guitar. With distortion and without distortion the sound is muddy and muffled. I should most likely list my equipment:

Shure SM57 - for recording acoustic and amp (Behringer )
Tascam US-428 - input for mics and guitars
IBM Thinkpad t42 1.6ghz notebook - DAW running Cubase 5

Guitar Impedance Loading/Buffering etc for Pedalboards

I had a most disturbing revelation today. My guitar tone sounded kind of wooly and lacked the dynamics that it used to, so I thought to myself "new strings"? But.. just to be safe, I tried unplugging from my pedalboard and straight into the amp. Lo and behold, the sound was brighter, LOUDER, and had a much greater dynamic range. I'm trying to figure out why this is...

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