Rise to Fame
Cheers needed to replace an actor who died mid-run, and Woody stepped in as the new bartender in Season 4 without anyone expecting much. He won an Emmy by 1989 and spent eight seasons playing the lovable simpleton while quietly stacking film credits. Natural Born Killers in 1994 finally buried the sitcom persona. Oliver Stone handed him a serial killer, and he made the character the most charismatic person onscreen. The People vs. Larry Flynt earned him his first Oscar nomination in 1996. Two more followed over the next two decades, which is not the career arc anyone predicted for the guy who replaced a dead bartender on TV.
In the Spotlight
The 2023 Saturday Night Live monologue where he compared vaccine mandates to a drug cartel scenario went viral for all the wrong reasons. It wasn't his first COVID stumble. In April 2020, he posted 5G-COVID conspiracy content to his Instagram and deleted it after backlash. Scientists publicly called the claims 'complete rubbish.' His public persona now carries a tension he doesn't seem to particularly mind: decorated character actor on one hand, committed conspiracy skeptic on the other. True Detective in 2014 and Three Billboards Outside Ebbing, Missouri in 2017 cemented him as one of the better actors working, but the SNL moment is what a lot of people remember now.
Side Notes
His father Charles Harrelson was a contract killer who shot a federal judge in Texas in 1979 for $250,000, earned two life sentences, and died at ADX Florence, the U.S. supermax, in 2007. Woody spent roughly $2 million in legal fees trying to get him a new trial, including hiring Alan Dershowitz. The appeals failed. His first marriage, to Nancy Simon (Neil Simon's daughter), happened in Tijuana in 1985 as what both parties described as a joke. They planned to annul it the next day, but the annulment office was closed. The marriage lasted ten months, which, given how the week started, was probably longer than expected.