Caddyshack II 1988

As the dynamic daughter of self-made real estate developer Jack Hartounian, who boasts both Armenian and Jewish roots, Kate finds herself adeptly maneuvering through the intricate layers of social standing. With aspirations to enhance her position, she unexpectedly bonds with the pretentious Miffy Young, a snobbish WASP who nudges both Jack and Kate to apply to the exclusive country club Bushwood—where, much to their surprise, the mischievous gopher from their prior escapades continues to stir trouble.

Nevertheless, the elite members of Bushwood are far from impressed by Jack’s offbeat methods in real estate development. Despite his affluence, he is regarded as an interloper due to his working-class background and his insistence on rejecting their entrenched old-money ideals. The sole individual who appreciates Jack’s character is wealthy widow Elizabeth Pearce, who perceives the depth beyond appearances. In stark contrast, Bushwood’s president, Chandler Young, deems the Hartounians to be “not Bushwood material,” essentially denying their enrollment.

As tensions mount, Jack finds himself at odds with the club’s haughty officials, including Cynthia Young and her son Todd, who attempts to manipulate Jack’s attorney, Peter Blunt, to their advantage, but to no avail. This breakdown in negotiations compels Jack to resort to extreme measures, leading to a bold auction of several club members—among them Chandler, Cynthia, Mr. Jamison, the Pierponts, and their so-called “secret slaves,” tasking them with labor on his construction site.

The rift between Jack and Kate widens as she forms a friendship with Harry, a caddy at Bushwood. Jack’s outrageous behavior only intensifies Kate’s sense of alienation. Following the club’s snub and the shutdown of his construction site by the freshly minted Historical Preservation Society, Jack reaches out to his friend Ty Webb, a wealthy individual and majority stakeholder at Bushwood.

With Ty’s backing, Jack seizes control of the club, rebranding it as Jackie’s Wacky Golf, a garish theme park that horrifies Chandler Young and the rest of the members. In retaliation, they enlist the services of Captain Tom Everett, a merciless mercenary, to eliminate Jack. As Kate becomes increasingly disenchanted with her father’s antics, she moves in with Miffy, signaling a significant shift in their lives.

The situation escalates when Chandler Young and Todd launch a series of legal maneuvers to financially ruin Jack, forcing him to concede both his construction project and the country club. Seeking an alternative, Ty proposes a high-stakes golf match between Jack and Chandler Young: should Jack lose, he must relinquish Bushwood and the housing project; conversely, if he triumphs, he keeps both. Unbeknownst to Jack, Chandler has cunningly arranged for Everett to eliminate him, but the plan goes hilariously awry when Everett accidentally targets Chandler’s prized Rolls-Royce instead.

As the decisive day approaches, Ty enlists Harry to serve as Jack’s steadfast caddy, prepping him adequately for the pivotal game. Meanwhile, Everett’s assassination plot is thwarted once again by the troublesome gopher, who proves to be increasingly irritating throughout the events. Although Jack initially struggles, he manages to level the playing field before facing an uphill challenge—the daunting task of making a 50-foot putt. Chandler is presented with a chance to equalize with an easy two-foot putt.

Throughout this layered saga, Everett’s bungled assassination attempt dramatically escalates when he accidentally injures himself in the rear with a poisoned dart. Amid fading patience for her father’s ceaseless blunders, Kate ultimately stands by Jack, setting aside her concerns about their family reputation. The gopher, ever the scene-stealer, cleverly swaps an explosive golf ball for Chandler’s, a move that irreversibly alters the outcome.

As Jack sinks what appeared to be an impossibly challenging putt, sealing his victory, both the Young family and their adversaries are left in utter disbelief. In the aftermath, Ty comes to the aid of Everett, who requires assistance extracting a poisoned dart—a minor consolation after the chaos that unraveled. In another corner, Peter mocks the misfortunes of Chandler, while Miffy confronts her mother over potential marriage plans with Chandler Young; Todd is overcome with fatigue, and Jack musters the courage to invite Elizabeth out on a date, which she graciously accepts. Amid the ensuing celebration, the gopher makes yet another appearance, this time with an unexpected affection for a poodle.