IFC film 1999-2007

Can't remember movie I watched on IFC around 1999 - 2007 I believe it was written, directed and acted in by two brothers, one brother escaped from a juvenile detention facility and kind of wander around ransacked someone's house stealing a cowboy hat, in the end he got into a small plane and fell asleep, the plane took off and police shot at plane hitting him and he died in the end.