Wholesome & Timeless: Inside Billy Crystal & Rob Reiner’s Five-Decade Friendship

The deaths of Rob Reiner and Michele Singer Reiner have left Hollywood and fans around the world in mourning. While the world mourns the loss of an icon and his beloved wife, among those grieving most deeply is Billy Crystal.

Crystal and Rob Reiner first crossed paths as costars, but over time their working relationship grew into a lifelong friendship. What began on a sitcom set in the 1970s evolved into a creative partnership that helped shape some of the most iconic films in modern cinema.

From “All in the Family” to “When Harry Met Sally,” Crystal and Reiner collaborated closely and remained a constant presence in each other’s lives, both professionally and personally.

Reiner and his wife, Michele Reiner, were found dead in their Los Angeles home in December 2025, a devastating loss that marked the end of a friendship that spanned decades and helped define a generation of storytelling.

How Billy Crystal and Rob Reiner First Became Friends

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He was 78. Crystal first met Reiner in 1975 after being cast as Al Bender, a friend of Reiner’s character on “All in the Family.”

“I hadn’t met Rob before, and here we were cast as best friends,” Crystal wrote in a guest column for The Hollywood Reporter in September 2016. “What impressed me the most about Rob was, one, he was so genial, but two, he was so smart … It’s a very impressive combination of talents that I first met — plus, he was just hilarious.”

Crystal recalled that Reiner was already shaping scenes behind the scenes.

“It was Rob who was fixing the script with the writers and the producers; it was Rob who was making sense out of what we had to do in the piece,” Crystal wrote. “He was so smart and so accurate and funny at the same time. And he was a terrific actor as well.”

After their on-screen dynamic clicked, the two decided to extend that bond beyond work.

“We became the closest of friends,” Crystal shared. “And when I moved out here, we just spent all kinds of time together.”

From Supporting Roles to ‘When Harry Met Sally‘

Reiner continued casting Crystal in his films through the 1980s. Crystal appeared briefly as Morty the Mime in “This Is Spinal Tap” in 1984 and as Miracle Max in “The Princess Bride” in 1987.

In 1989, Reiner made a pivotal decision. He cast Crystal as Harry Burns opposite Meg Ryan in “When Harry Met Sally,” even though he had considered other actors for the role.

“Whenever you do something this personal and you’re best friends, if it doesn’t work, it’s like, ‘Oy!’” Reiner told People in 2019. “Finally, I said, ‘Aw f*** it; he’s perfect!’”

Crystal’s contribution became legendary. “The biggest laugh in any film I’ve ever done was a line Billy came up with: ‘I’ll have what she’s having,’” Reiner said.

Crystal later recalled sitting beside Reiner at the first screening.

“Rob and I were sitting in the back next to each other. Then the orgasm scene happens, and the place goes berserk,” Crystal told The Hollywood Reporter in 2016. “When Rob’s mother, Estelle, says, ‘I’ll have what she’s having,’ it was thunderous.”

A Friendship That Lasted Through Life’s Hardest Moments

The two continued to support each other across decades, from premieres to panels, including appearances together at San Diego Comic-Con in July 2025 and the premiere of “Spinal Tap II: The End Continues” in September 2025.

After the death of Reiner’s father, Carl Reiner, in 2020, Crystal spoke about the family bond they shared.

“He was an uncle to me,” Crystal said during a January 2021 appearance on “The Late Show with Stephen Colbert.” “Rob is my dearest friend.”

Crystal added, “He was just a giant. I mean really a giant.”

That closeness was visible again in the days following Reiner’s death.

Footage obtained by USA Today showed Crystal walking near Reiner’s home with his wife, Janice Crystal. A neighbor said he “looked like he was about to cry.”

Billy Crystal Breaks His Silence After Rob Reiner’s Death

After the deaths of Reiner and his wife, Michele, Crystal joined a group of close friends and longtime collaborators in a statement shared with the Associated Press.

“Going to the movies in a dark theater filled with strangers having a common experience, laughing, crying, screaming in fear, or watching an intense drama unfold is still an unforgettable thrill,” the statement read.

“Absorbing all he had learned from his father Carl and his mentor Norman Lear, Rob Reiner not only was a great comic actor, but he also became a master storyteller.”

The tribute continued, “There is no other director who has his range. From comedy to drama to ‘mockumentary’ to documentary, he was always at the top of his game.”

The group also reflected on Reiner not just as a filmmaker, but as a collaborator who made those around him better.

“For the actors, he loved them. For the writers, he made them better. His greatest gift was freedom,” they wrote.

The statement closed with a line from “It’s a Wonderful Life,” one of Reiner’s favorite films.

“Each man’s life touches so many other lives, and when he isn’t around, he leaves an awful hole, doesn’t he?”

For Crystal, the words captured a friendship that lasted a lifetime and a loss felt far beyond the screen.

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