Leonard Kraditor (Joaquin Phoenix), in a major depression after a recent heartbreak, moves back into his childhood home with his parents, Ruth (Isabella Rossellini), and Reuben (Moni Moshonov). His parents try to play cupid with Leonard's love life, matching him with a long time family friend's daughter, Sandra Cohen (Vinessa Shaw). Sandra's parents, Michael (Bob Ari) and Carol (Julie Budd), also agree with the arrangement and welcome their families coming closer together. The Cohen's will be buying and taking over Leonard's family run dry cleaning business. And although Sandra is a truly loving, caring and adoring girl, his eyes are focused on the exciting new girl, Michele (Gwyneth Paltrow), he's discovered living in his same building, Seemingly so much out of Leonard's league, Michele keeps calling out her window to him and running into Leonard that he finds himself becoming completely infatuated with her lifestyle. So much so, that even when he finds out Michele is dating an older married man who's ripping her heart out, Leonard still continues to passionately fall in love with her, while valuing just being her friend.
Meanwhile, Leonard's parents are pushing him into this ideal relationship with Sandra, forcing him to make an impossible decision between Michele, the one who has reignited his lust for life, or Sandra, who will offer him comfort, love and security while possibly sending him back into the massive state of depression from his boring former life.
2009 - National Board of Review - Best Independent Film
2929 Productions, Wild Bunch, Tempesta Films, Magnolia Pictures
Director: James Gray
Writers: James Gray, Ric Menello
Producers: Anthony Katagas, Donna Gigliotti, James Gray