The years between The People vs. Larry Flynt (1996) and No Country for Old Men (2007) were the years of consolidation and diversification: he continued making films across a wide range of genres, maintained a public persona that was increasingly defined by his personal commitments — hemp advocacy, environmental causes, a lifestyle that was organized around the values he held about sustainability and natural living — and took roles that reflected his taste for moral complexity without always receiving the critical attention that the early films had generated.
He was also, in these years, continuing the appeal effort on his father’s behalf. The Dershowitz involvement and the 1998 federal court testimony by Charles both belong to this period. The experience of being an Oscar-nominated actor with the resources to fund a high-profile legal effort, while the father you are trying to help remains in federal prison, produces a specific kind of biographical tension: the son’s success has created the capacity to help, but the help cannot undo what the father did or what the law has concluded about it.
## Messenger, Hunger Games, and the Breadth of a Later Career
The Messenger (2009) was the film that produced his second Oscar nomination, this time for Best Supporting Actor. Oren Moverman’s drama about the Army’s Casualty Notification Officer program — the soldiers tasked with delivering death notifications to the families of soldiers killed in combat — placed Harrelson as the senior officer who trains and mentors the younger soldier played by Ben Foster. The role required restraint and interior depth rather than the physical energy and surface charisma of his earlier standout performances: Sergeant Stone is a man whose professional purpose is to deliver the worst possible news as humanely as possible, whose personal life is a quiet wreck, and whose relationship with the Foster character develops into the kind of genuine friendship that extreme professional circumstances can produce.