He won the Outstanding Supporting Actor Emmy in 1989, in his fifth season. The award was recognition of the specific quality of his performance in a specific season, but it also marked his arrival as someone the industry took seriously rather than as a competent cast member in a successful show.
His personal life during the Cheers years included his brief marriage to Nancy Simon — the daughter of Neil Simon, the playwright whose Biloxi Blues had given him his understudy work when he first arrived in New York. The marriage took place in Tijuana in 1985, described by Harrelson as an impulsive decision. It lasted approximately ten months. The specific circumstances of its end are not extensively documented, though “whimsical Tijuana wedding that lasted less than a year” describes a recognizable category of young adult decision-making that requires no further elaboration. He has spoken about it with the kind of rueful lightness that time and a successful subsequent marriage make available.
The Cheers years were also the years of his most regular contact with his father. The prison visits — approximately once a year, according to his 1988 People account — were conducted during the years when the character he played on television was as far from a convicted killer as it was possible to get. Woody Boyd was uncomplicated moral sunshine. Charles Harrelson was serving consecutive life terms. The contrast existed, and Woody lived in it, apparently without the contrast becoming something that required public performance or resolution. He visited his father. He made his show. He received his Emmy nominations. He continued.