The Bachelor 1999

As Charlie Samson (played by) navigates the complexities of being a devoted husband and aspiring accountant in Manhattan, he’s suddenly faced with the life-altering news that his wife is expecting their first child. The weight of this responsibility prompts him to re-examine his readiness for fatherhood, just as he’s preparing to take on the role of best man at his colleague Arnold Craig’s impending nuptials.

The evening before the wedding, Charlie and four fellow bookkeepers - including Walter, a seasoned married man struggling with the diagnosis of asthma, and Eddie, a carefree bachelor - gather for a raucous bachelor party. As they screen explicit short films at one member’s apartment, their revelry soon gives way to bar-hopping, marking a pivotal moment in the lives of these five men.

For Charlie, the night becomes a testing ground for his loyalty to his wife as he narrowly avoids an affair with a captivating stranger met on the streets of Greenwich Village. Meanwhile, his young wife at home is rocked by her visiting sister’s revelation about her own husband’s infidelities, casting doubt on the institution of marriage.

As the evening wears on, Walter becomes increasingly despondent over his health, eventually wandering off in despair. Arnold, once the picture of enthusiasm for impending matrimony, succumbs to intoxication and a crisis of conscience, ultimately calling off the wedding. However, after sobering up and receiving a heartfelt pep talk from Charlie about the benefits of married life - despite Charlie’s own earlier reservations - Arnold changes his mind.

As the night draws to a close, we find Eddie striking up an unlikely conversation with an older woman at a bar, a poignant reminder that even those who seem to have it all can be searching for something more. Ultimately, Charlie comes to realize that building a life with his wife is a worthwhile endeavor, far preferable to the empty existence he once envied in his friend Eddie.