Sensing that her modeling career was winding down, Macpherson looked to other ventures such as broadcasting (she hosted several TV specials, including "Supermodel of the World") and designing (a lingerie line in New Zealand and Australia that has since become a $10 million enterprise). She has also backed the chain of Fashion Cafes with fellow models Claudia Schiffer, Naomi Campbell and Christy Turlington.
Macpherson made her film debut in a bit part as a party guest in Woody Allen's "Alice" (1990), then went on to co-star with Hugh Grant and Sam Neill in the Australian-made "Sirens" in 1994. 1996 was a busy year for Macpherson, with three films released. The indie "If Lucy Fell" was a pallid comedy in which she portrayed the neighbor and love object of Eric Schaeffer. A nice change of pace was "Charlotte Bronte's 'Jane Eyre'", directed by Franco Zeffirelli, in which Macpherson had a supporting role as Blanche, a snooty debutante. In Barbra Streisand's big-budget disappointment "The Mirror Has Two Faces", Macpherson dumped boyfriend Jeff Bridges, leaving Barbra to pick up the pieces. She landed roles in two 1997 big-budget actioners, Joel Schumacher's "Batman & Robin" and Lee Tamahori's "The Edge". In the former, she was the romantic interest of George Clooney's Bruce Wayne, while in the latter, Macpherson was cast opposite Alec Baldwin as a survivor of a plane crash.