Kiss of the Spider Woman being the first. His second was the highly anticipated but ultimately disappointing Ironweed, released in 1987. It earned its stars, Jack Nicholson and Meryl Streep, Oscar nominations, but I think was ultimately too downbeat to capture the public's interest.
Base on a Pulitzer Prize-winning novel of the same name by William Kennedy, which happens to be one of my favorite books of all-time, Ironweed is part of Kennedy's Albany Cycle, a series of books about the interconnected Phelan and Quinn families. Ironweed is about Francis Phelan, a one-time baseball player who lives as a bum, punishing himself for accidentally killing his baby son.
Phelan is played by Nicholson, and if anyone needs a reminder that he was a great actor and not just a personality should watch this film. Sure, the trademark Nicholson grin comes out a few times, but his role is downplayed. He is a beaten man, haunted by ghosts of the men he is killed (one was Nathan Lane, a scab in a trolley strike whom young Francis stoned in the head). He has an on-again off-again relationship with Helen (Streep), who struggles to maintain her dignity though neither one knows where they will sleep from night to night. Nicholson's acting when he visits his son's grave is about as good as it gets.
The crux of the plot is Nicholson's decision to return home again. His wife (Carroll Balker) and son (Michael O'Keefe) are forgiving, not so much his daughter (Diane Venora). The scene, which he meets his grandson and shows him a baseball signed by Ty Cobb, has a lovely nature to it, but the whole film needed some quicker pacing. There is no redemption for anyone, which can work in a piece of literature but is tougher to pull off in a film.
There is also a scene in which concerned local citizens raid a hobo camp, which has no foreshadowing and no context. The film is set in 1938, so I imagine there was a lot of homelessness in those days.
I think the scene everyone knows from the film, if they know one at all, is when Streep, once a nightclub singer, gets a chance to belt out "He's Me Pal." Her imagining of how it goes is quite different than reality, and her attempt to maintain her pride is just heartbreaking.
Ironweed was a noble effort, but ultimately a failure. Perhaps some books can not be made into good movies.