Natalie Portman in "Love and Other Impossible Pursuits."

Credit: TIFF

Writer/Director Don Roos is a really funny guy.  And he's pretty talented too.  His breakout flick "The Opposite of Sex" has grown in stature as one of the quintessential indie movies of the late 1990s.  Unfortunately, he's never really duplicated the magic of the dark comedy that helped convince Hollywood Christina Ricci had real sex appeal.  His latest film, "Love and Other Impossible Pursuits," debuted today at the Toronto International Film Festival for press and industry and to say it's a disappointment is an understatement. 

Adapted from a novel by Ayelet Waldman, "Impossible" centers on a young New York city legal associate Emilia (Portman) and Roos has done pretty much, um, the impossible with her.  He's taken a young woman who has lost her baby only months before and made her completely unlikeable and unsympathetic.  The first 20 minutes or so finds Emilia bickering and insulting her 8-year-old stepson Jack (an OK Charlie Tahan) while flashbacks reveal she systematically seduced his father, a senior lawyer at her firm who also happened to be married at the time.  She pretty much treats everyone like [expletive] that you don't understand why even her "best friends" (an underused Anthony Rapp and Lauren Ambrose) are in the picture at all.  "Impossible" also follows a number of storylines (including an unnecessary plot device of having Emilia's father having cheated on her mother) whose sole point seems to be to show just how caring, screwed up and unappealing Portman's character is.  So, when you get to the pivotal scene where Emilia has a revelation on the fate of her deceased daughter, you don't really care.  It's almost pointless and the tacked on happy ending feels like an afterthought.

Part of the problem is that like Roos' grating romantic drama "Bounce," "Impossible"  suffers from trying to have too much of a glossy, commercial sheen on the proceedings.  His underrated "Happy Endings" allowed him to rebound from "Bounce" because it was precisely less stereotypically Hollywood.  The filmmaker clearly wants to be serious but have his cake and eat it to by incorporating the writer's trademark snarky one-liners.  It completely disrupts the tone and turns too many of the characters, such as Charlie's mother Carolyne (played by Lisa "I've done this bitchy role way too many times before" Kudrow) into caricatures.  Portman was obviously intrigued by the dramatic arc of her character -- she's an executive producer on the project -- but everyone involved failed to realize how difficult it would be for any actress to pull it off.  Even someone as talented as Portman.

It's hard to imagine mini-major such as Fox Searchlight, Miramax or Focus acquiring "Impossible," but the independent production may get a deal with a Magnolia or IFC willing to use Portman's star power on a VOD deal. 

For constant updates on awards season and entertainment news follow Gregory Ellwood on Twitter at Twitter.com/HitFixGregory

Needless to say, "Impossible Pursuit" indeed.