Supernatural's Sam Winchester started as a law school student but ended up hunting demons with his brother instead. Despite wanting to settle down and leave the hunting life behind, the show's ending didn't pay off Sam's original goal. While it's unclear what profession he ended up in, Sam did get married and have a child named after his brother, and eventually stopped hunting. However, his son having an anti-possession tattoo on his deathbed shows that hunting was still part of their family legacy. It would've been nice to see the brothers retire together and leave hunting behind for good.