At 72 years of age, actor Sam Elliott has played cowboys in Tombstone and The Big Lebowski and then switched tracks appearing in romantic dramas and comedies such as I'll See You in My Dreams and Grace and Frankie (as Jane Fonda's beau). In this film, he is Lee Hayden, an actor known for starring roles as a cowboy hero. In the opening sequence, he's in a studio taping an ad for barbecue sauce; the man in charge is a perfectionist who has no qualms about pushing Hayden to do just one more take. It is humiliating.
The actor's patience and resilience is tested further when his doctor tells him that there is a malignant tumor in his pancreas. Looking for a place to escape this harrowing news, Hayden pays a visit to his weed-smoking buddy Jeremy (Nick Offerman) where he meets Charlotte (Laura Prepon), a flirtatious 35-year-old stand-up comedian who admits to having a thing for old guys. Can this December and May relationship bloom or is it doomed from the start?
Hayden struggles with his legacy when he goes to a banquet where he is given a lifetime achievement award from the Western Appreciation and Preservation Guild. Charlotte goes along for the ride. He flounders through his speech, which surprises everyone by going viral. Soon scripts are filling the office of his happy agent who sees Hayden on a comeback path. But more tension arises when the cowboy listens to Charlotte's comedy club sketch on the vicissitudes of sex with old geezers.
Brett Haley directs this drama that showcases Sam Elliott's durability as the mythological cowboy who repeatedly rides off into the sunset, alone with his mortality and faded dreams. His cowboy character wins our empathy as he tries desperately to make up for his failings. This comes across most vividly in his fumbling attempt to re-establish a connection with his estranged daughter Lucy (Krysten Ritter). We also respect his resilience as he tries to move beyond the heartbreak of broken relationships with women. In the end, all he wants is what all cowboys yearn for — to be free as a bird.