Wealthy Yemeni American brothers Steve (Will Ferrell) and Doug Butabi (Chris Kattan) thrive on the nightlife, often found in clubs where they enthusiastically nod to the infectious beats of Eurodance. However, their attempts at charming women are consistently thwarted, leading to their ejection from various venues due to complaints about their antics. Their ultimate goal is to gain entry into the illustrious Roxbury, a legendary Los Angeles nightclub, but a formidable bouncer (Michael Clarke Duncan) keeps blocking their path.
Despite receiving an $80 ticket from a striking police officer (Jennifer Coolidge) while speeding, Steve’s meager flirtations go unnoticed. Back at home, the brothers share a room and work during the day at their family's artificial plant store, owned by their affluent father, Kamehl Butabi (Dan Hedaya). The brothers often slack off, dreaming big about launching their own club where any wannabe can feel like a celebrity. Doug, on the other hand, uses his credit card responsibilities as a guise to flirt with a telephone operator he dubs "Credit Vixen" (Meredith Scott Lynn).
Their store shares a wall with a lighting emporium owned by Fred Sanderson (Dwayne Hickman), whose daughter Emily (Molly Shannon) is smitten with Steve. However, Doug holds a grudge against Emily, claiming his brother is off the market, as they live life on the edge.
After a sun-soaked day at the beach, the brothers are determined that tonight is the night they will finally step foot in the Roxbury. However, a clash with their father about skipping a planned dinner with Emily and her family results in their privileges being stripped away. Instead, their mother, Barbara (Loni Anderson), gifts them enormous cell phones for emergency use but limits their access to their BMW, instead giving them the artificial plant store's delivery van. They once again face rejection at the Roxbury's entrance.
A chance encounter after a minor accident with actor Richard Grieco allows the brothers to leverage his fame and gain entry into the highly coveted club. Inside, the brothers pitch their vision to Benny Zadir (Chazz Palminteri), the club’s owner, who is intrigued by their plans to create a nightclub where the outside mirrors the inside—a concept they excitedly elaborate on. He appreciates their creativity and arranges a follow-up meeting.
While at the club, they attract the interest of two women, Vivica (Gigi Rice) and Cambi (Elisa Donovan), who mistakenly believe the brothers to be wealthy, leading to unexpected romantic entanglements for Doug and Steve. An evening filled with quirky troubles unfolds as they continue to annoy Zadir's driver, Dooey (Colin Quinn), while sharing wild ideas like covering the pool with a glass top for a unique dancing experience.
However, the following day presents a setback when Dooey denies them access to Zadir, falsely asserting that Zadir was inebriated and forgot about their meeting. The brothers later face heartbreak when the women realize the truth about their financial situation, prompting a fallout between them and the Butabi brothers. Doug and Steve find themselves arguing about the blame for their misfortunes, leading Doug to vacate their shared room.
Just as Steve is about to enter a forced engagement with Emily in a backyard ceremony orchestrated by their father, Doug makes a flamboyant entrance fueled by fluffy whip, ultimately causing a stir and halting the wedding. This leads to a moment of reconciliation between the brothers, but only after comedic chaos unfolds, revealing the truth currently surrounding the engagement.
When Doug and Steve finally reconnect with their father and mend their relationship, the story culminates as they discover a brand-new club that uncannily resembles the vision they had pitched to Zadir earlier. To their surprise, their names await them on the VIP list, as Zadir, in a twist of fate to honor their creativity, makes them part-owners of the new venue, showcasing the brothers' journey full circle as they bump into the very women from their past, igniting new sparks of potential romance.
