I haved worked on sound from both aspects: as a musician, and as a soundman.

The Italian singer could NOT hear what he sounded like in the audience. All he heard was the stage monitor mix. At some point the musician has to trust the sound engineer to do an acceptable, attractive sound mix for the house speakers.
As to a clean sound, I think most music listeners are conditioned to accept radio quality in the music they hear--and radio quality is definitely low fidelity audio. Or it could be that the clean sound your dad likes is not as warm as others might prefer. Perhaps adding a little bit of delay or reverb, or a change in mics could make the sound more appealing...