Milla Jovovich is Olive, a single Ukrainian-immigrant mother caring for her progeny, in Bringing Up Bobby, a film whose only relatable element is the absolute disdain felt by Olive's boyfriend, Walt (Rory Cochrane), for the titular kid (Spencer List). That scorn is largely born from her fawning over the twerpy kid like he's a perfect prince rather than a punkish delinquent who cares nothing for school but plenty for the illegal shenanigans perpetrated by his dear old mom, a thief and scam artist on the run for crimes committed in Kansas City. Landing in Oklahoma, Olive continues to coo over Bobby and argue with Walt while stealing cars from dealer lots and defrauding old men out of pizza, hijinks that actress turned writer-director Famke Janssen shoots with a breeziness that immediately feels undeserved, in large part because Olive and Bobby are, from the get-go, an unctuous pair, so full of each other and their inside-joke-y rapport that they alienate at every turn. Of course, even if they weren't a smug duo, they'd still resound as a phony one, thanks to both a turn by List that's nothing but enthusiastic mugging and a Ukrainian accent by Jovovich that, though the actress attempts to take Olive's increasingly troubled plight seriously, leaves the character feeling like a cast-off from an SNL sketch, minus the punchlines.
While Jovovich often sounds like she's doing a bad impersonation of Sesame Street's Count von Count, there are also other off-putting verbal inflections in Bringing Up Bobby, courtesy of Bill Pullman and Marcia Cross, who both affect a Southern twang as wealthy parents still grieving over their dead son—and who, through a series of convenient circumstances, come to adopt Bobby after Olive winds up in the slammer. Janssen opts for over-the-top melodrama whenever possible, so that more than one sequence features mother and son tearfully being pulled away from each other set to the sounds of earnest soundtrack tunes. And once Olive is released from the big house and again starts interfering with Bobby's maturation process, the film takes a steep turn into obviousness, with the story transforming into one long waiting game for Olive to realize that her felonious lifestyle isn't the best example to set for a troubled kid trying to figure out how to grow up. That Very Important Lesson culminates with Bobby pulling a Columbine-style prank that lands everyone in hot water, though such heavy-handed plotting is by that point unnecessary, given that a preceding scene in which Bobby steals a dress from his adopted mother to give to Olive makes plain that Bringing Up Bobby is just an extended dramatization of the 1980s anti-drug PSA that memorably cautioned, "I learned it by watching you!"