Take a bunch of inmates and put them into a house. Not like murderers/rapists and things like that, but also not small crimes. Trying to hit the sweet spot between serious, but not too serious. Like severe destruction of property (but not harming any actual living beings), or theft above a certain threshold. These are people who chose to commit crimes, and would do so again given half a chance.
These people would be made aware of exactly what their housemates did, and also have to deal with the stress of being constantly on camera, ala big brother. They each get one day, separate from the rest, to go to town and do whatever they want. They can do charity work/community service for bonus points or an edge in the next challenge, or just blow the day doing whatever. If they're caught doing anything illegal, they're immediately eliminated, and their sentence is increased appropriately.
One day a week, which no one is allowed to have off, there is a challenge. Each challenge is designed to aid the community in some small way. After three challenges, there scores are tallied up, and the lowest scoring person goes home.
Last man standing receives $25,000 and can go free, regardless of the length left on their sentence. Should it be that enough people are eliminated before the actual scoring period, then the last person must make it to the end of that month, when elimination would normally be held.
Now, you may be thinking that this is boring, or just a plain bad idea. But there are two kickers.
1: Unbeknownst to our contestants, events are staged, tailor made to entice our little inmates to wander from the straight and narrow, increasing in payout, and therefore becoming more tempting, as the show goes on. Perhaps someone will leave their little cherry-red sports car running while they head into a shop that our felon was just leaving. Or maybe someone will leave an easy to pocket, but quite expensive doodad out in the open while they're distracted. The contestants will have to fight their baser urges, ones they've already succumbed to before.
2: Once you've been on the show, you don't leave. You're not followed by cameras anymore, and you may have peace of mind, but you still have to follow the rules. If, for any reason, you should be on the wrong side of the system again, you'll be forced to forgo your winnings. Paying anywhere between 1x-2.5x the prize money as compensation to the ones you've wronged, depending on the crime. Not only that, but those years you lost will be added back onto your new sentence.
Just need to work on a name for it.