Herbert Ross Director, Producer Whoopi Goldberg Jane Actor Mary-Louise Parker Robin Actor Drew Barrymore Holly Actor Matthew McConaughey Abe Actor James Remar Alex Actor Billy Wirth Nick Actor Anita Gillette Elaine Actor Dennis Boutsikaris Massarelli Actor Estelle Parsons Louise Actor Amy Aquino Anna Actor Stan Egi Henry Actor Stephen Gevedon Johnny Figgis, Jane's Band Actor Amy Ray Indigo Girl Actor Emily Saliers Indigo Girl Actor Jude Ciccolella Jerry Actor Gedde Watanabe Steve Actor Jon Seda Pete Actor Mimi Toro Carrie Actor Lori Alan Girl With Attitude Actor Mary Anne McGarry Dr. Newbauer Actor Danielle Shuman Young Robin Actor Julian Neil Nightclub Owner Actor Niecy Nash Woman at Diner Actor Ted Zerkowski Drug Buyer Actor Jill C. Klein Waitress Actor Marnie Crossen Nurse Actor Aaron Lustig Judge Actor Terri White Female Guard Actor George Georgiadis Cab Driver Actor Arnon Milchan Producer Steven Reuther Producer