I've had a problem with the parable of The Prodigal Son ever since first hearing it in Sunday School. Look at it from the good son's perspective, and there's no reward for being good; look at it from the perspective of the errant younger son, and there's license to screw up as long as you want, as long as you recant in the end. But what if you look at it from the father's perspective?
I'm a school-teacher; I work in a small private school. We use a lot of incentive programs and token economies with the kids. One day last year, one of my students who has a horrible track record with turning in homework actually turned it in on time. I quickly praised her and gave her a gold star (literally. My kids are big on stickers.) Of course, this started an uproar from the rest of the class. They had done their homework, and they wanted stickers, too. Without really knowing where I was headed (and feeling a little weird about bringing up a Bible story), I asked if anyone knew the parable of the Prodigal Son. One kid did, and was happy to relate it, casting himself and his friends in the starring roles. (In his updated version, the younger son ends up working at McDonald's, not for pay but for scraps...)
When my student finished telling the story, I told my kids how I'd never liked it, and always thought it was unfair. But thinking about it in terms of my classroom, I found it suddenly made sense. Pupils who do well, and get good grades, and complete their homework are rewarded; they know that they're successful, they feel good about themselves, and they don't constantly have that sinking, guilty feeling that they're about to get in trouble. I don't value my honor roll students any less than the ones who don't do well, but I do make more of a fuss over the underachievers when they are successful. They need the positive feedback. They need reinforcement of their good behavior. They aren't getting the subtle, intrinsic rewards that the good students take for granted.
So maybe this is the point. Maybe the older brother just wasn't aware of how good he had it. Maybe it's not about how much squandering you can fit in before you have to come crawling back, looking for forgiveness. Maybe the parable is supposed to be viewed from God's perspective, from the point of view of a shepherd who wants all of his flock safe and close by.