Nearly a decade prior, Ryan had dropped out of a part Roberts eventually played so that she could star in When Harry Met Sally.

GREGG DEGUIRE

With Pretty Woman, Notting Hill, and My Best Friend’s Wedding, Julia Roberts has starred in some of the best romantic comedies of all time. But as fate would have it, she could have added another to her impressive roster: 1998’s You’ve Got Mail.

While promoting her latest film, the psychological thriller Leave the World Behind, on Thursday’s episode of Watch What Happens Live With Andy Cohen, Roberts was asked to reflect on any roles she regretted turning down. Instead, the Oscar winner shifted the question to share two movies she passed on that “maybe wouldn’t have been as great and wonderful” with her in them.

One was 1992’s The Last of the Mohicans, starring Daniel Day-Lewis. The other? You’ve Got Mail, in which she would have acted opposite Tom Hanks and played Meg Ryan’s part as hopelessly romantic bookshop owner Kathleen Kelly.

Instead of Roberts, who went on to star with Hanks in 2007’s Charlie Wilson’s War and 2011’s Larry Crowne, Ryan reunited with her Sleepless in Seattle love interest. That same year, Roberts opted to coheadline the domestic tearjerker Stepmom alongside Susan Sarandon.

Nearly a decade prior, it was Ryan who was originally cast as Shelby in 1989’s Steel Magnolias, a part based on screenwriter and playwright Robert Harling’s sister, Susan.

“The day after we cast her, she came to us in tears and said, ‘I’m sorry, but I just got offered this film, and I’ll be a leading lady with Billy Crystal…’” Harling recalled last year. “So you know we said, ‘Of course, go make When Harry Met Sally.’”

It was Sally Field, who plays Shelby’s mother, M’Lynn, in the film, who suggested producers meet with Roberts, according to Harling.

“Sally said, ‘You know, there’s this girl and she’s been off making some movie about a pizza. She’s Eric Roberts’s sister,’” he told Southern Living, referencing her breakout role in 1988’s Mystic Pizza. “We brought her in, and she was Julia Roberts, so she was magic. She just walked into the room and lit it up, and I thought, That’s my sister.”

On WWHL, Roberts also mentioned the Steel Magnolias switch, which helped earn her the first of four Academy Award nominations. She noted that she also nearly missed out on her earliest project with the late filmmaker Mike Nichols.

“Cate Blanchett was supposed to be in Closer, but she got pregnant, and so then I got that part,” Roberts said of the 2004 romantic thriller costarring Natalie Portman, Jude Law, and Clive Owen. “So I’ve lucked into some good stuff.”