The Bachelor 1999

As Charlie Samson (played by Chris O’Donnell) navigates the intricate landscape of being a dedicated husband and an aspiring accountant in the heart of Manhattan, he receives life-changing news—his wife is expecting their first child. This unexpected development forces him to confront the monumental responsibilities of fatherhood just as he is set to assume the role of best man for his colleague Arnold Craig (also played by Chris O’Donnell) at his upcoming wedding.

On the eve of the wedding, Charlie joins four fellow bookkeepers, including Walter, a seasoned married man grappling with the challenges of asthma, and Eddie, a laid-back bachelor, for a wild bachelor party. In a friend’s apartment, they indulge in a night filled with explicit short films that transitions into a bar-hopping escapade, setting a transformative stage for their lives.

For Charlie, the night serves as a true test of loyalty to his wife as he narrowly sidesteps the temptation of an affair with an intriguing stranger he meets while wandering the streets of Greenwich Village. Back home, his wife is shaken by her sister’s startling revelation about her own husband’s infidelities, igniting doubt about the durability of marriage itself.

As the hours pass, Walter grows increasingly troubled by his health and ultimately slips away into the night, while Arnold, who was once brimming with excitement for his impending marriage, spirals into drunkenness and a profound crisis of conscience, leading him to call off the wedding. However, after a sobering moment and an earnest pep talk from Charlie about the merits of married life—despite Charlie’s own earlier uncertainties—Arnold regains his resolve.

As the night draws to a close, we witness Eddie engage in an unexpected dialogue with an older woman at a bar, highlighting the notion that even those who appear to have it all might still be yearning for something deeper. Ultimately, Charlie comes to the realization that forging a life with his wife is a noble and fulfilling pursuit, one that stands in stark contrast to the hollow existence he previously admired in his friend Eddie.