Bobby and Olive standing in front of the car that they stole.
In the heartland of America, Olive (Milla Jovovich), a single mom originally from the Ukraine, spends her life conning others. Her cons have included stealing a car (the opening scene), stealing a pizza dinner, conning the members of a religious group into believing that she runs a religious shelter in Europe and taking their money. Later we learn that Olive also was responsible for a series of suspicious fires in Kansas City. The rest of her life is occupied with doting on her ten-year-old son Bobby (Spencer List). Bobby, born in America, has never had a father in his life. He has been raised as a free spirit like Olive, undisciplined and encouraged to participate in her scams. The two clearly love each other. They call each other Bonnie and Clyde as they go from Kansas to Oklahoma, a few steps ahead of the law. Most of Bobby’s actions rub other people the wrong way, like their very conservative, religious neighbor who spouts bible verses and freaks out when his son and Bobby pretend to have their own rock band.
Bobby is introduced to the class at his new school.
Olive has one other friend, Walt (Rory Cochrane), who she can turn to for help. Walt has no love for Bobby, who he sees as a delinquent punk kid wrongly fawned over by Olive. To Walt’s chagrin, Bobby’s over the top behavior is encouraged by Olive at every turn. Their life together is one inside joke after another. They don’t seem to realize that their behavior alienates others. Their lack of any moral compass is something that will eventually come back to haunt them. Bobby doesn’t care about doing well at school because he doesn’t like anyone telling him what to do. Bobby is actually very bright, quoting memorized lines from films like Gone With the Wind and the Pirates of the Caribbean but lacks a work ethic when it comes to school work. Another element comes into their lives when Bobby is skateboarding out in the street with a couple other neighborhood boys. He is accidentally hit by a distracted driver Kent (Bill Pullman) who turns out to be a wealthy businessman in town. Kent is very sorry for the accident, and Bobby is rushed to the hospital for treatment. Kent takes care of everything and gives Olive his business card. Bobby is not badly hurt at all but Olive immediately goes after the insurance company, trying to scam them into believing that Bobby was badly traumatized by the accident. Kent and his wife Mary (Marcia Cross) both take a liking to Bobby and Olive. They recently lost their own son; helping Bobby meets a need they have in their lives.
Bobby is climbing up the wall, literally.
Things suddenly change in Olive and Bobby’s lives when Olive’s past catches up to her and she is arrested at a bowling alley in quite dramatic fashion — the two are literally pulled apart from each other as she is taken into custody. Separated from Bobby and desperate, she brings in Kent and Mary, who agree to adopt Bobby so that he won’t be put into the foster care system on a permanent basis. Kent and Mary explain to Olive that there are conditions attached to the adoption. If she wants to regain custody of Bobby once again, she will have to settle down, get an honest job, and show proof of stability in her life. Olive is released from prison eight months later. When she returns to visit Bobby at Kent and Mary’s elegant house, things have already changed. Bobby is thrilled to see her, and wants to know if they can live together again. But they both already know the answer to that question, at least for the time being. Kent says that they can set up visiting times on a schedule. Having Olive back in his life does not turn out well for Bobby, who continues to make bad choices in his daily life. No longer can everything he does be described as the mischievous pranks of an innocent kid. That lack of a moral compass gets him into very hot water. Now Olive must decide what is the best path for Bobby to travel to avoid having a life style like hers with the same disastrous results.
Bobby spends time with wealthy businessman Walt and his wife Mary.
Bringing Up Bobby is the first film written and directed by actress Famke Janssen. One gets an uneven impression from viewing it. On the one hand is the comedic element presented to us as a series of pranks against pompous and clueless people. This contrasts with the dramatic element of a kid being raised without any sort of moral compass or sense of discipline. If it wasn’t for the convenient intervention of the Bill Pullman and Marcia Cross characters, Bobby would have been taken into custody by the state and placed in a foster home. Ultimately Bobby’s future is up to Olive. This dichotomy is present in the character of Bobby. On the one hand we see him as a typical mischievous kid; on the other hand he is an annoying mama’s boy who gets your hackles up by his bad decision making and bad attitude. Some credit has to be give to Spencer List for his acting performance that gets such a variety of reactions. Despite her over the top accent, which could be attributed to part of the con, Milla Jovovich gives an interesting performance as Bobby’s mom, at first wild and crazy, then sad and repentant, as the significance of what she has done to her son sinks into her conscience. Bill Pullman and Marcia Cross are excellent in their portrayal of the wealthy married couple who eventually bring some stability into Bobby’s life. If nothing else, Bringing Up Bobby is an interesting character study of life in a small town.
Bobby walks down the wrong path with his friend, Sam.
Bobby talking on the telephone.
Spencer List is seen wearing black high top or blue low cut chucks in many of the scenes. They are the perfect footwear for a kid with attitude and issues like Bobby. The two best scenes with chucks are at the very beginning when Bobby and Olive are test driving the used car they are about to steal and Bobby sticks one of his chucks up on the dashboard. The second scene is when Bobby is making a phone call to pull a prank on Walt.
Bobby sticks his foot up onto the front window while riding with his mother.
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