In 1982 Brooklyn, a boy named Charlie Carbone is about to become the stepson of a crime boss named Salvatore Maggio (Christopher Walken). The mobster's juvenile delinquent apprentice Frankie Lombardo (Michael Shannon) tries to drown Charlie (he throws a long pass at the beach into the water and asks Charlie to retrieve the ball, when Charlie didn't know how to swim), but a boy named Louis Booker (Anthony Anderson) saves him and they become best friends. That was the only day Louis got Charlie out of trouble.. For the rest of his life Louis reminds Charlie that he saved his life and gets him into trouble. Twenty years later, in 2002, Charlie (Jerry O'Connell) now runs his own beauty salon and Louis still remains his best friend, but Sal's henchmen take a majority (80%) of the salon's profits, leaving Charlie very little for improvements. After they botch the job of hiding some stolen television sets (This was Louis's deal and he wanted Charlie's help to hide the TVs before he can make the delivery), resulting in the discovery of Sal's warehouse (after being chased by the police, only 5 sets remain intact which Louis takes to Sal's warehouse, and are followed by the police in a helicopter) and the arrest of at least one of his men, Sal gives Charlie and Louis one more chance. Under instructions from Frankie, they are to deliver a package to a man named Mr. Smith (Marton Csokas) in Coober Pedy, Australia. Frankie also warns them against opening the package "under any circumstances" and to call Mr. Smith at the phone number he gives them should they run into any trouble. Unknown to Charlie and Louis, however, Sal tells his Capo (Tony Nikolakopoulos) that he is "canceling their return trip." On the plane, Louis opens the package, against Frankie's warnings, to find $50,000 in cash. Upon landing in Australia (Charlie is so afraid that he is strip searched by the customs, but luckily Louis had taken the envelope and hid inside his jacket), they rent a Land Cruiser and head to Mr. Smith. Along their way, they accidentally run over a red kangaroo. Thinking it is dead, Louis puts his "lucky jacket" on the kangaroo and with Charlie's sunglasses to pose for photographs as a joke, as he thinks the kangaroo looks like "Jackie Legs", one of Sal's henchmen from Canarsie. The kangaroo then suddenly regains consciousness and hops away with one problem; the $50,000 was in the jacket. Charlie and Louis get into their car and try to reclaim the money from the jacket on the kangaroo, but the ensuing chase ends with the duo crashing through a field of termite mounds and then into a pile of rocks, wrecking the car. At a pub in Alice Springs, Louis manages to call Mr. Smith and tries to explain their situation. Mr. Smith, however, thinks they stole his package and threatens to kill Louis and Charlie, telling him that they had better have the money ready when he meets them, or he'll "chop them into snags and feed them to the crocodiles"; he then plans to find them himself. Smith tracks the number to the bar from where Louis called him. Back in New York City, Sal gets the call from Mr. Smith saying that Charlie and Louis haven't arrived; Sal then sends Frankie and some men to Australia to investigate. Meanwhile, Charlie and Louis attempt to reclaim the money from the kangaroo by shooting it with a tranquilizer dart from a biplane (Louis had met a girl Jessie from the wildlife foundation, who gave him this idea after hearing his story). The attempt fails when Louis accidentally shoots Blue (Bill Hunter) the pilot and strands the trio in the desert. Louis asks Blue to point them to the nearest wildlife foundation center, hoping that they run into Jessie. They spend many hours wandering in the desert, during which Charlie hallucinates about a jeep, and they soon meet a woman from the Outback Wildlife Foundation called Jessie (Estella Warren), who Louis previously met in Alice Springs. Thinking she is only a mirage, Charlie grabs her breasts and she knocks him out with her canteen. While unconscious, Charlie dreams about meeting a speaking, rapping version of the kangaroo, while Sal and Louis mock him in kangaroo forms. Meawhile Blue stayed with the plane and tried to fix his radio. He gets it working, but his location is heard by Mr Smith, who then severs the connection. Smith gets to Blue and finds where Louis and Charlie are headed. The following day, the trio get on camels (Jessie agrees to help them when Charlie offers a $2000 grant to her foundation. Louis had told her that the Kangaroo had their passports, and nothing about the $50K) then track the kangaroo at the nearby Todd River and try again to catch it with bolas (They cover themselves to mud to cover their human scent and get close to the Kangaroo), but Louis accidentally botches their attempt when a swarm of ants crawls up his pants. While waiting for the next opportunity to catch the kangaroo, Charlie begins developing feelings for Jessie, which she claims not to return at first, but he senses that she is lying. The next day, Mr. Smith and his henchmen arrive and capture the trio. Smith takes Jessie with him to track the Kangaroo, and orders his men to kill Charlie and Louis. Charlie and Louis turn the tables (Louis cuts their ropes by taking a scissor hidden in Charlie's pockets) and outsmart them, only to find Frankie has tracked them and is prepared to kill Smith, Charlie and Louis. Just as he is about to however, the kangaroo suddenly returns causing a fist fight between Mr. Smith's henchmen and Frankie's crew, who outmatch them. The distraction allows Charlie, Louis, and Jessie to escape on their camels. A final three-way chase ensues, with Charlie, Louis and Jessie chasing after the kangaroo while being pursued by Frankie and his goons. Louis finally manages to retrieve the money from the kangaroo but ends up nearly falling down a cliff and is narrowly saved by Charlie and Jessie. After getting the money back, Charlie tries to hand it over to Frankie once and for all, but the latter angrily declines and reveals that Sal really sent them to Australia to pay for their own execution at the hands of Mr. Smith much to the shock of Charlie and Louis. Out of nowhere, the police force led by an undercover cop Mr./Sgt. Jimmy Inkamale (David Ngoombujarra) arrive and arrest Frankie, Mr. Smith, and their respective henchmen. Charlie and Louis call each other true friends, and Charlie reclaims Louis' lucky jacket from the kangaroo (it was proven lucky as otherwise they would have delivered the money to Smith and ended up dead), who turns out to have a family. One year later, Charlie and Jessie are married and have used Sal's $50,000 to start a line of new hair care products bearing a kangaroo logo, and Louis has become Charlie's advertising partner. Frankie, Mr. Smith, and their men have been imprisoned for life as has Sal who has failed at using his high-level connections to avoid arrest as mentioned in Charlie's narration where the newspaper states that he is currently on trial. The kangaroo, now called "Kangaroo Jack", is still happily living in the outback. Now able to speak again, Jack breaks the fourth wall, explaining why the film should end with him and closes it with his version of Porky Pig's famous catchphrase "That's all, blokes!"
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