Actually ? I don't know anyone that's served time in prison personally, so that's a new one on me. Doesn't sound like much to be proud of though.
It is disturbing. They wear it as a badge of courage and "I paid my dues".
No. I know many, including several family members who have been in a revolving door and they're happy to keep going back. Its no big deal to them.
I once knew a man who served 6 years, out 30 days, returned to serve another 5 years. Happy camper.
I haven't known anyone who was proud of it. Quite the opposite. In one case, he doesn't want anyone to know, and he's worked hard to live a better life. Prison was their wake up call. It was either prison or death.
I have only seen reference to that on TV or in the movies and have never met anyone like that. Anyone I know who went to prison wanted to put it behind them and move on with their lives. Of course doing time limits your job opportunities.