I have two to recommend. They are both what used to be referred to as women’s films, with huge female ensemble casts, about family drama and shades of grey moral dilemmas.
The first is Margaret (2011), starring HBO‘s TrueBlood‘s Anna Paquin as a high school student at a Manhattan upper middle class private school for upper west side Jews. Matt Damon plays a married teacher she hooks up with, Allison Janney, Jean Reno, and Mark Ruffalo round out the cast along with dozens of theater actors, including one really good one, J. Smith-Cameron, as Paquin’s mom.
Paquin flirts with a passing bus driver (Ruffalo) on her way to school and he hits a pedestrian and kills her. Paquin lies during the investigation, worried that she will destroy the poor working class bus driver’s life if she tells that he was a distracted driver. Then later she second guesses this decision, and approaches relatives of the victim, initiating a legal case against New York City and its bus system. It’s interesting how none of these people are as moral or intelligent as they think they are, and how the system and the survivors grind out settlements that have little to do with justice. (Also: should left-liberal Hollywooders be making movies in which teen (half-)Jewesses are such vixens they run about like sirens, wrecking marriages and buses?)
The second is Evening (2007) with an unbelievable cast, including HBO‘s Homeland‘s Claire Danes, Glenn Close, Meryl Streep, Toni Collette, Vanessa Redgrave, Hugh Dancy, Eileen Atkins, Barry Bostwick and Natasha Richardson. It’s all flash back from the death bed of Vanessa Redgrave, attended by daughters Collette and Richardson, to the Newport, Rhode Island wedding party where Danes (as the young Redgrave) is a bridesmaid and both she and the bride (and maybe the bride’s brother, played by Dancy, who proposes to Danes in the movie, and married her in real life after meeting her in this movie) are all in love with a young doctor who is not the groom. It’s a good movie, though Danes does Danes, with the cocked head and hair swinging and thoughtful mugging, and Collette does Collette, the slightly freaky person who stares at you, the same characters you’ve seen them do (very well) before. It’s one of those bittersweet movies where you survey the whole life and wonder whether the characters should have all made different choices in their twenties. Regrets, they have a few.