Molly's Game was marketed as an insider look at the high stakes poker world, we get a couple of those every decade, but it's actually a middling study of ego penned by famed screenwriter Aaron Sorkin in his directing debut. Jessica Chastain stars as Molly Bloom (not the James Joyce character) a champion skier who went on to manage some of the most lucrative poker games in Los Angeles and later New York during the 2000s. Despite a first rate cast and Sorkin's trademark hyper-drive dialogue, Molly's Game disappointingly never strikes the right tone, wavering between all knowing "this is how the world really works" sequences and strained attempts to make these cold characters engaging.
Molly's Game opens with an annoying montage sequence with Molly informing us on her family's awesome accomplishments. Kevin Costner, growing more insufferable with each year, plays her "driven" father Larry who demands greatness from his children (he's a prominent psychiatrist.) Costner's speechifying as the tough love Dad comes off as obnoxious, verging on self-parody. Determined to prove she can make it on her own, Molly skips law school moves to L.A. and gets a job as a personal assistant for sketchy real estate dealer Dean Keith (Jeremy Strong) who verbally berates her, but eventually allows Molly to run his high stakes poker nights that include power players from the entertainment industry. In time she's running her own games. After A-list actor "Player X" (Michael Cera) buys her out Molly relocates to New York City.
Once the story shifts to New York, we enter into Scorsese lite territory. We see elite, beautiful people flaunting their money as they pull the levers of the global economy. The Russian mob gets involved. Idris Elba co-stars as Molly's lawyer and brings a conscience to the film to a thankless role. The scenes between Elba and Chastain do achieve a compelling dynamic.
Chastain's believable, but her character motivations are never fully explained, other than wanting to make money. But, for what? In a problematic scene towards the end, Molly's estranged father Larry (Costner) randomly shows up and psychoanalyzes her! It's a strange moment to select for a film's emotional high point. Almost every set piece features Molly playing opposite a man, usually in negotiation, and she does hold her own, but the never ending verbal warfare gets wearisome, especially for a 140 minute movie.
Sorkin's memorable scripts for Steve Jobs (2015) and The Social Network (2010) were keen insights into character and ambition in the 2000s, while Molly's Game explores similar themes, it never hits the dramatic heights of those two films.