Cameron Crowe’s semi-autobiographical film Almost Famous, about the fictional folk rock band Stillwater in the early 1970s, was a breakout hit for star Kate Hudson. Hudson played the mysterious Penny Lane, winning a Golden Globe and earning an Academy Award nomination for the role. But according to Crowe, Natalie Portman, who was a much more well-known actress at the time, was originally in the running. In fact, several of the film’s major parts were initially intended to be occupied by bigger names.

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Image via DreamWorks PIctures

Speaking with host James Andrew Miller on the Cadence13 podcast  “Origins: Almost Famous Turns Twenty," Crowe described how his initial choice for Stillwater’s lead guitarist Russell Hammond was Brad Pitt. As reported by RADIO.COM, the director said “Brad Pitt was on my mind because I had a really good meeting with him around the time of Say Anything, and he was just starting out, and he just really had something,” he said. “So I called him with this to play Russell Hammond, and we spent about four months working on it. He read with Natalie Portman.” And screen legend Meryl Streep was being considered for the role of Elaine Miller, the mother of lead character William Miller (Patrick Fugit), who goes on tour with Stillwater to document the experience for Rolling Stone. Of course, the role ultimately went to the inimitable Frances McDormand, but it’s interesting to picture Streep terrifying the aloof Russell into finally granting William an interview.

Pitt ultimately passed on the project, which devastated Crowe. “I wept. I knew that [Brad Pitt] had never fully fallen in love with the character. He had fallen in love with the idea of the character. But maybe there just wasn’t enough on the page.” Crowe speculated a bit on why Pitt decided to vacate the role, which wound up going to Billy Crudup. “He told me [money] wasn’t the case. I think it was probably half and half. I think he was also uncomfortable with the age difference between Russell and Penny Lane.”

You can listen to the entire episode on the RADIO.COM app. For more Hollywood near misses, read about which iconic Mad Max: Fury Road character was nearly cut from the film.