It certainly would influence my hiring decision. Not a show stopper, but certainly a minor negative. Probably the damage done by lost opportunities for experience would be worse than having a record, though. That even functions as an excuse of sorts--I suspect I'd actually like someone who was in prison for five years and got a degree over someone who lived off a trust fund for five years and did nothing.
All depends on the person, though, and what exactly I'm hiring for. And someone coming out of prison after 20 years? The fact that they committed a crime is long past, but it's hard to overstate how damaging decades in prison is. People have a really hard time adjusting, and any hire of someone like that I did would be out of charity, not out of expecting to get any value out of the person. If they manage to do well, I'd take that as an unexpected plus.
