Happy Endings advances on three intercut narrative fronts. Fortyish and unhappy, Mamie (Lisa Kudrow) is the survivor of a bad marriage and now works as a counselor in an abortion clinic where she's not very helpful to her clients. Mamie is pro-choice, but she nonetheless rejected abortion for herself when she became pregnant by her step-brother Charley (Steve Coogan) when both were teens. Today, Mamie is sexually involved with Javier (Bobby Cannavale), a Mexican-American immigrant who works as a masseur. Mamie likes the physical aspect of her connection with Javier well enough, but she's openly contemptuous of the idea that their relationship will ever become anything more. Then out of the blue, student filmmaker Nicky (Jesse Bradford) shows up with a wild, even extortive proposal. He will introduce Mamie to the son she gave up for adoption two decades ago if she will let him film the reunion. In a movement typical of this picture's complications, Nicky's original proposal morphs into the massage documentary.
Meanwhile, step-brother Charley, who manages the restaurant business he and Mamie inherited from their deceased parents, has long since discovered his homosexuality and lives happily with Gil (David Sutcliffe). These two gay men have a close and caring relationship with a lesbian couple, Pam (Laura Dern) and Diane (Sarah Clarke), so close that Gil donated sperm when Pam and Diane were trying to conceive a child. Pam and Diane have a child now, but they maintain Gil is not the biological father. When the men get to doubting that fact, all manner of bad behavior breaks out.
Last, we meet a busboy named Otis who hears a woman named Jude (Maggie Gyllenhaal) singing karaoke in Charley's restaurant. Otis asks Jude to become the vocalist in the nowhere band he serves as a rhythmless drummer. The band itself exists only because of the support of Otis's rich dad, Frank (Tom Arnold). Jude sizes all things up quickly and concocts a despicable plot to seduce Otis and then blackmail him so she can mooch off Frank. This third storyline serves to illustrate the old adage "be careful what you wish for."
As is almost inevitably true with films featuring so many characters, not all are treated equally or in the final analysis satisfactorily. Javier's story is resolved as a kind of punchline to a dirty joke; he ends up with a client fond of his skill at delivering happy endings. Nicky, too, is allowed to drift away, and what we're ultimately told becomes of him seems consistent enough with his neurotic self-obsession but not with his surprising talent. There's a better, nastier but more successful end for Nicky than the one Roos has devised.
Even the three stories themselves are unbalanced. Mamie's and Jude's narratives lead somewhere convincing and thematically important while Charley and Gil's story dissolves into inconsistency. We can buy the suspicion arising over the baby's parentage and even the deceit Charley employs in search of the truth. But Pam and Diane respond with a viciousness that borders on cruelty not moored in their characters as portrayed earlier. They become mean rather than, more appropriately, disillusioned.
But these are mere bubbles of complaint amid a sea of admiration. Mamie and Jude are richly imagined, deeply complicated, convincingly human characters. They are flawed, and they are selfish in their profoundly different ways. But however many times they disappoint us, Roos keeps us from giving up on them. And one has to hail Roos' unconventional faith in family, even dysfunctional family. A desire for blood tie, after all, is what drives Charley's mischief and what ultimately binds him to Mamie. It's what makes Mamie want to know her son and -- however much he's a blockhead -- makes Frank a hero.
Happy Endings is also notable for its performances. As she did under Roos' direction in The Opposite of Sex, Kudrow proves that her talents are hardly limited to comedy. Her Mamie is as richly realized a character as the big screen will deliver this year. Gyllenhaal is comparably brilliant. Her Jude is a sexpot who perhaps actually finds herself. And Tom Arnold (yes, Tom Arnold) is a revelation as a man whose most valuable organ lies not hanging between his legs but thumping in his chest.