The story is set in 1965 and centers on three teenagers from Los Angeles: Woody (Tom Cruise), Dave (Jackie Earle Haley), and Spider (John Stockwell). Driven by the pressures of puberty and male ego, they boldly embark on a cross-border road trip to Tijuana, Mexico, with one specific mission: to lose their virginity in the local legal red-light district.
The journey in a 1957 Chevrolet quickly spirals into layered chaos. First, Dave’s young younger brother, Wendell, secretly sneaks into the car trunk. Second, along the way, they cross paths with Kathy (Shelley Long), a frustrated adult woman intent on getting a quickie divorce in Mexico. Upon arriving in Tijuana, their expectations of an instant night of fun instantly collapse. The group of teens finds themselves trapped in a whirlwind of trouble involving local thugs, corrupt police, and even a chase by rampaging Marines.
The film's success in keeping the audience engaged stems from its character dynamics. Tom Cruise, who was only about 20 years old at the time, portrays Woody with a compelling mix of innocence and natural charisma. Unlike his aggressive and reckless friends, Woody serves as the group's moral compass. His chemistry with Shelley Long adds an unexpected emotional dimension for a low-budget teen comedy, allowing their relationship to grow beyond mere shallow physical attraction.
In terms of cinematography and direction, Curtis Hanson successfully captures the wild, noisy, and neon-lit atmosphere of the border town, creating a sharp contrast with the innocence of the characters. The presence of character actors like Jackie Earle Haley also injects a cynical, explosive comedic energy. The first half of the film is filled with fairly solid situational humor, exploiting the nervousness of know-it-all American teenagers dealing with the harsh reality of Mexican nightlife.
However, the film's narrative structure stands out as its main weakness, leaving the second half feeling unbalanced. Hanson executes a tonal shift that is far too drastic: a film that opens as a relaxed, lighthearted sex comedy suddenly morphs into a somewhat dark crime drama. The scenes of detention, threats of physical violence, and the climactic car chase feel overly serious, sacrificing the comedic elements built from the start.
Additionally, as a period film set in the 1960s, Losin' It is considered careless with its historical details. Numerous visual anachronisms slip onto the big screen, ranging from the actors' hairstyles and clothing styles to the appearance of 1970s and 1980s production cars on the streets, which shatters the illusion of the past.
Overall, if you are looking for a clever comedy with a deep moral message, Losin' It may feel cliché, formulaic, and dated. Conversely, if enjoyed as a cinematic time capsule—a fun retro feature to watch a megastar like Tom Cruise hone his acting chops at the dawn of his career—then this film remains an engaging piece of '80s pop-culture entertainment well worth a look.