After the little white lies of Romy and Michele's High School Reunion (1997), director David Mirkin focuses on scheming of a different sort in Heartbreakers. Sigourney Weaver and Jennifer Love Hewitt play Max and Page Conners, a mother and daughter who share everything with each other: relationship advice, hair and makeup hints, and the money they win in costly divorce settlements with rich men. When the film opens, the Conners are putting the finishing touches on conning Dean (Ray Liotta), an auto-body shop owner. When the dust from that scam clears, Page announces she's ready to move away from her mother and set up shop on her own -- but in order to clear an outstanding debt, Max insists they bankrupt one more bachelor together. They settle upon phlegmatic Palm Springs widower William B. Tensy (Gene Hackman), a chain smoker with a heart of gold and a similarly bountiful bank account. Only two things stand in their way: Tensy's Teutonic caretaker Miss Madress (Nora Dunn) and beachfront bartender Jack (Jason Lee), a wry stargazer with whom Page becomes unexpectedly smitten. Heartbreakers is the third collaboration from writers Steven Mazur and Paul Guy, whose previous screwball comedy was 1997's international hit, Liar Liar.
by Michael Hastings synopsis