Madeleine Stowe in Worth Winning (1989)

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Some suave and moneyed lady killers have all the luck. Test your resistance to lifestyle envy by observing the chick-rich exploits of the charmed mesmerist whose sensual excesses provide the dramatic impetus to the endearing relationship comedy Worth Winning (1989). So enamored is Worth Winning’s hero of his fully requited Casanova complex that he accepts a wager from three of his lesser-blessed brethren that requires him to secure marriage proposals from three women of his pals’ picking. Pride, we all know, goes before a fall, the most humbling descent of all being that fall into love.