In 1982 Brooklyn, young Charlie Carbone is about to become the stepson of a notorious crime boss named Salvatore Maggio. During a brief yet dangerous moment, the delinquent apprentice Frankie Lombardo attempts to drown Charlie in the water, but he's saved by a brave boy named Louis Booker. This incident marks the start of a lifelong friendship, though it often finds Charlie in trouble, with Louis consistently reminding him of his heroic act that day.
Fast forward to 2002, Charlie, portrayed by Jerry O'Connell, now operates his own beauty salon, while Louis, his ever-loyal best friend, still stands by his side, albeit with complications. Sal's henchmen seize a staggering 80% of the salon's profits, leaving Charlie barely enough to keep his business afloat. When a covert job involving stolen TVs goes awry, resulting in a combative encounter with police, Sal gives Charlie and Louis a last chance to prove their worth. They are tasked, under Frankie's orders, with delivering a mysterious package to a man named Mr. Smith in Coober Pedy, Australia, with strict instructions not to open it.
However, Louis, unable to resist curiosity, opens the package mid-flight to discover $50,000 in cash. Upon landing, they embark on their quest but encounter unexpected chaos after accidentally hitting a red kangaroo. Mistakenly believing the kangaroo is dead, Louis dresses it with his "lucky jacket" and they take funny pictures, only for the kangaroo to hop away with the jacket — and their money — sparking a frantic chase.
Later, at an Alice Springs pub, Louis attempts to connect with Mr. Smith to explain their predicament, but the response is far from favorable. Mr. Smith threatens their lives, insisting they have the money ready upon their encounter. Meanwhile, back in New York, Sal gets wind of their delay and sends Frankie to retrieve them, tightening the noose around Charlie and Louis.
In a bid to recover their lost money from the kangaroo, they opt for a wild plan involving tranquilizer darts, which backfires spectacularly, leaving them stranded in the desert. They fortuitously meet Jessie, a woman from the Outback Wildlife Foundation, who agrees to help them in exchange for a grant. Amid their adventures, Charlie finds himself developing feelings for Jessie, though she initially gives him mixed signals.
Their misadventures escalate as Mr. Smith and his men capture the trio, only for Charlie and Louis to turn the tide and escape in an unexpected showdown involving Frankie, leading to an exhilarating final chase on camels. After a series of unexpected events, including a dramatic confrontation with both the kangaroo and the mobsters, the true nature of their mission reveals itself — they were sent to Australia to meet their demise.
But just as danger seems inevitable, the police arrive in the nick of time, apprehending Frankie, Mr. Smith, and the rest of the criminals. Ultimately, Charlie and Louis find solace in their friendship, reclaiming the lucky jacket from the kangaroo, which has proven invaluable.
Fast forward a year later — Charlie and Jessie are happily married and have successfully launched a new line of hair care products featuring a kangaroo logo, and Louis has stepped into Charlie's creative advertising ventures. Meanwhile, their former adversaries are behind bars, facing justice. To cap it all, the beloved kangaroo, now named "Kangaroo Jack," enjoys a happy life in the outback and humorously breaks the fourth wall, concluding the story with a playful rendition of "That's all, blokes!"
