Billy Crystal reveals his honest reaction when Rob Reiner offered him 'When Harry Met Sally' role

Billy Crystal has opened up about how he landed his iconic role in When Harry Met Sally..., revealing that his close friend and director Rob Reiner initially considered several other actors before offering him the part.

In an exclusive interview with People, the 78-year-old actor reflected on the making of the beloved 1989 romantic comedy and his creative partnership with Reiner, who died alongside his wife, Michele Singer Reiner, in December 2025.

Crystal admitted that learning he was not Reiner's first choice to play Harry Burns opposite Meg Ryan's Sally Albright was difficult, although he understood why his friend wanted to explore other options.

“It was difficult in that I was not his first choice for Harry,” Crystal said.

The actor recalled accepting that Reiner needed to consider different performers for the role. Albert Brooks, Tom Hanks and Michael Keaton were among those reportedly considered for the part before Reiner ultimately approached Crystal.

“I said, ‘Listen, when he wants me, if he wants me, then he wants me. But I know he's seeing other people, which he should do,’” Crystal recalled.

When Reiner eventually called, he reportedly reassured his friend that he had always envisioned him playing Harry but wanted to see other actors first.

Crystal's response was characteristically humorous. After Reiner asked him to read the screenplay, the actor joked that someone had secretly given him the script and that he did not like it. The pair then burst into laughter before discussing how they could approach the film.

“I have a lot of ideas,” Crystal remembered telling Reiner. The director responded by suggesting they begin working the following day.

Crystal ultimately contributed significantly to the film's dialogue and character development, bringing his own ideas to Harry rather than simply following Reiner's interpretation.

“It was great to do them because Rob was Harry,” Crystal explained, referring to the director's personal connection to the character. Reiner was going through a divorce from actress and filmmaker Penny Marshall during the film's development, experiences that helped inform Harry's emotional journey.

Crystal said he eventually had to tell his friend to step back so he could develop his own interpretation of the character. Reiner understood the request, allowing the actor to bring his perspective to the role.

Some of the romantic comedy's most memorable moments also emerged from their conversations outside the screenplay. Crystal recalled regularly speaking to Reiner late at night, with their discussions inspiring scenes that became central to the film.

One example was the sequence in which Harry and Sally watch Casablanca together over the phone from their separate apartments. Crystal said the idea drew on his frequent late-night conversations with Reiner while the director was navigating his personal life.

The pair also developed the film's famous exchange about a headache and the possibility of having a tumour. Crystal recalled Reiner complaining about a headache during a phone call and dismissing the suggestion that he see a doctor because he expected the doctor would tell him it was nothing.

“And it's one of my favourite little exchanges,” Crystal said. “That was pure us.”

Released in 1989, When Harry Met Sally... became one of the most celebrated romantic comedies of its era. Written by Nora Ephron and directed by Reiner, the film explores whether men and women can maintain a friendship without romantic feelings eventually complicating their relationship.

Crystal's performance helped establish Harry Burns as one of the genre's most recognisable characters, while the film's dialogue and New York setting have kept it popular with audiences across generations.

Reflecting on the collaboration, Crystal's memories highlight how his friendship with Reiner shaped the film beyond the casting decision itself. What began with uncertainty over whether he would get the role ultimately developed into a creative partnership that helped produce one of Hollywood's most enduring romantic comedies.