When Richard Dreyfuss Passed on When Harry Met Sally: ‘Not a Great Script’

When Harry Met Sally is one of the greatest rom-coms of all, and as director Rob Reiner explained this past weekend, Richard Dreyfuss could have played the role that went to Billy Crysyal.

Reiner discussed the film in a roundabout way while speaking at the 2025 TCM Classic Film Festival to mark the 35th anniversary of his film Misery alongside the film's star, Kathy Bates, who won an Oscar for her portrayal of deranged romance book fan Annie Wilkes.

When asked about the many actors who were up for the male lead in Misery — the part of author Paul Sheldon, who was ultimately played by James Caan — Reiner mentioned that one was Jaws and Close Encounters of the Third Kind star Richard Dreyfuss.

He explained that he had offered Dreyfuss the lead of his film before 1990's Misery, 1989's When Harry Met Sally, but that Dreyfuss had passed on the idea for what seems, in retrospect, like the most surprising of reasons.

"We met a little bit, He said, 'You got a great director, but not a great script. 'And I thought, Geez, Nora Ephron was a great screenwriter," Reiner recalled.

Oscar voters concurred: Ephron's script for When Harry Met Sally was nominated for an Academy Award. Audiences embraced the film as well, making the film a huge hit, and dramatically raising the profiles of both Harry (Crystal) and Sally (Meg Ryan).

"So now, When Harry Met Sally becomes a huge hit, I call him up about this," Reiner recalled, referring to Misery." "And he says, 'I'll do it, whatever it is.' And then he turned this down."

Dreyfuss loss was again another actor's gain: Misery was another massive hit.

Also Read: 10 '90s Rom-Coms You Won't Have to Fake Excitement About

Besides Richard Dreyfuss, Other Potential Stars of Misery and When Harry Met Sally

Reiner also discussed some of the other actors he sought for the James Caan role in Misery, including Robert Redford, William Hurt, and Warren Beatty.

Reiner said Beatty was so interested in Misery that he met with him several times to work on the script after William Goldman turned in his take on the Stephen King adaptation. He said Beatty offered a very interesting take on the film, in which Annie holds Paul captive and forces him to write her a new book.

"He said, 'This is not a horror movie. This is not a thriller. He said, This is a prison movie. That's what you have to think about. ... This man is in jail, and he has to be as smart as you guys are in trying to figure out how to get out of jail," Reiner said.

The Misery panel also included Reiner recounting how he knew Bates was right for the role as soon as she started auditioning, and their disagreement about whether Annie should cut off Paul's feet, or hobble him — as she ultimately does in the film.

“I was crushed that you took that out,” Bates told Reiner of his decision to tone down the film's violence by letting Paul keep his feet.

The TCM Classic Film Festival was been a treasure trove of cool film lore for lovers of classic films. Among the other highlights was George Lucas, at a 45th anniversary screening of The Empire Strikes Back, explaining why the 900-year-old Jedi master Yoda talks the way he does.

When Harry Met Sally, meanwhile, has aged well — it was even resurrected this past year for a Super Bowl ad, in which Crystal and Ryan revisited the film's most famous scene, the deli sequence in which Ryan's Sally proves, very publicly, how easy it is to fake sexual satisfaction.

Main image: When Harry Met Sally. Columbia Pictures.