Mother and son con artist team, Olive (Milla Jovovich) and ten year old Bobby (Spencer List) travel across Oklahoma pulling outrageous scams whilst staying one step ahead of the law. A Ukranian immigrant escaping a troubled past, Olive tries to be a good mother by encouraging Bobby to study hard for a brighter future, even though the boy’s behavioural problems stir up no end of trouble at school. When wealthy businessman Kent Thomas (Bill Pullman) accidentally hits Bobby with his car, he and his kindly wife Mary (Marcia Cross) go out of their way to help the boy and his mother. Having lost their own son only a short while ago, the pair happily step in to take care of Bobby after Olive is unexpectedly hauled away by the police. Eight months later, Olive leaves prison determined to stay on the straight and narrow in order to regain custody of her beloved son.
Written and directed by Famke Janssen, onetime Bond girl in Goldeneye (1995) and star of X-Men (2000) and Taken (2008), Bringing Up Bobby emerges an awkward though not uninteresting hybrid of earnest social drama with a style of quirky midwestern comedy not far removed from Napoleon Dynamite (2004). On this evidence Janssen has an endearingly eccentric sense of humour as she stages some strange comic scenes as when Olive’s disreputable sidekick, Walt (Rory Cochrane, who previously co-starred with Jovovich in Richard Linklater’s outstanding Dazed and Confused (1994)) adopts a Cockney alter-ego called Gerard Butler (!) to convince insurance investigators about Bobby’s injuries. Nevertheless the amoral antics of the self-satisfied protagonists are often less amusing than Janssen evidently believes them to be.
Although far from autobiographical the film nevertheless draws extensively upon Janssen’s own observations as a European immigrant in the USA. It presents a cockeyed view of rural Americana filtered through the sardonic yet pop culture inflected perspective of an East-European chancer, reinforced by the soundtrack bookended by Jovovich’s storming cover of the Ike and Tina Turner standard “Proud Mary” (sung in her native Ukranian) and the closing version of “Amazing Grace” performed by The Flaming Lips. There is a faintly patronising aspect to the film’s portrayal of mid-westerners as obese, bible-thumping hicks who easily fall for Olive’s over-the-top con routines implying stupidity makes them deserving victims.
However, the cartoonish tone of the first half gradually gives way to a more compellingly dramatic second half. Janssen’s unfocused screenplay omits some crucial background information (it glosses over Olive’s eight month incarceration and reveals little about Bobby’s father who plays a crucial role in events) but the twin plot strands detailing the effect Bobby has on Kent and Mary and Olive’s sad realisation that walking away from her son might be the best thing for all concerned provide many of the more sincere, tender and moving moments. Still, the film gives no sense that Bobby regards the Thomases as anything more than a meal ticket. Despite an able performance from young Spencer List, Bobby emerges something of a smart-mouthed brat. His obnoxious pranks may well prevent some viewers from growing involved in his plight. Janssen draws lively, vivid performances from a fine ensemble cast spearheaded by a charismatically vivacious turn from Milla Jovovich, clearly relishing the chance to flex her acting muscles once again away from the increasingly vapid Resident Evil movies.