Season 1 2006 | 9 episodes The season 1 of Twenty Good Years aired from Oct 11, 2006. Cast (4) Heather Burns Jeffrey Tambor John Lithgow Jake Sandvig Crew (6) Michael J. Leeson Producer.he Terry Hughes Producer.he Tom Werner Producer.he Jimmy Miller Producer.he Eric Zicklin Producer.he Eric L. Gold Producer.he Images Posters Similar Series An American in Canada Ann Jillian Diana Take Five