Billy Crystal and Rob Reiner may have started out as costars - but their working relationship soon blossomed into a five-decade friendship. In 1975, Crystal was cast as Rainer's friend Al Bender in All in the Family. "I hadn't met Rob before, and here we were cast as best friends," Crystal recalled in a guest column for The Hollywood Reporter titled "Billy Crystal: How Rob Reiner and I Built a Bromance of Four Decades" 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." Reiner cast Crystal in small roles in 1984's This Is Spinal Tap and 1987's The Princess Bride before choosing him to star in the 1989 hit When Harry Met Sally alongside Meg Ryan. What Rob Reiner Said About 'When Harry Met Sally' Sequel Months Before Death "Whenever you do something this personal and you're best friends, if it doesn't work, it's like, 'Oy!'" Reiner told People in a 2019 interview on casting Crystal in the film. "Finally, I said, 'Aw, f*** it; he's perfect!'" The twosome continued to show up for each other throughout the years at various premieres, including at the premiere of Reiner's Spinal Tap II: The End Continues in September 2025. In December 2025, Rob and Michele Reiner were found dead in their Los Angeles home. He was 78 years old. Keep scrolling to learn more about Crystal and Rob's decades-long friendship: 1975 Billy Crystal and Rob Reiner in 'All In the Family' Everett Collection Crystal was cast opposite Rob in All in the Family as Rob's character Meathead's pal Al Bender. Crystal shared that he thought Rob was "so genial" and "so smart" after meeting Rob. How Rob Reiner's Love Story With Wife Michele Changed 'When Harry Met Sally' "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 shared in a guest column for The Hollywood Reporter in September 2016. "He was so smart and so accurate and funny at the same time. And he was a terrific actor as well. It's a very impressive combination of talents that I first met - plus, he was just hilarious." After their onscreen relationship "worked really well," Crystal and Rob decided that since "it feels right onstage, why don't we just continue this in our lives?" "We became the closest of friends. And when I moved out here, we just spent all kinds of time together," Crystal gushed. 1984 Crystal made a brief appearance as Morty the Mime in Rob's directorial debut, This Is Spinal Tap. 1987 Crystal briefly appeared as Miracle Max in Rob's film The Princess Bride. 1989 Billy Crystal, Rob Reiner and Meg Ryan on set of 'When Harry Met Sally...' Everett Collection After making brief appearances in This Is Spinal Tap and The Princess Bride, Rob cast Crystal in the lead role of Harry Burns opposite Meg Ryan in When Harry Met Sally. Although Rob considered other actors such as Albert Brooks, Tom Hanks and Michael Keaton for the part of Harry, he decided Crystal was "the best one." Kevin Bacon and More Stars React to the Deaths of Rob and Michele Reiner "Not only did [Crystal] nail it, but he contributed like crazy," Rob shared on The Howard Stern Show in 2016. Rob noted that "whenever you do something this personal and you're best friends, if it doesn't work, it's like, 'Oy!'" "Finally, I said, 'Aw f*** it; he's perfect!" Rob told People in 2019."The biggest laugh in any film I've ever done was a line Billy came up with: 'I'll have what she's having.'" One of Crystal's favorite memories with Rob happened at the first screening of When Harry Met Sally. "Rob and I were sitting in the back next to each other. Then the orgasm scene happens, and the place goes berserk," Crystal recalled to The Hollywood Reporter in 2016. "When Rob's mother, Estelle, says, 'I'll have what she's having,' it was thunderous, a laugh you can only hear with the best of jokes in a concert hall. It's those moments that make movies so spectacular. ... We just grabbed each other's hands because we knew something exciting was about to happen with this movie." 2021 Billy Crystal, Carl Reiner and Rob Reiner MARK RALSTON/AFP via Getty Images After Rob's father Carl Reiner's death in June 2020 at age 98, Crystal praised Carl and showed support for Rob. "He was an uncle to me, and Mel [Brooks] has been the same way. That's one of the great blessings," Crystal shared during an appearance on The Late Show with Stephen Colbert in January 2021. "Rob is my dearest friend and then Carl and I had a whole separate, wonderful relationship where we would speak and talk. He was just a giant. I mean really a giant." July 2025 Crystal and Rob appeared at a San Diego Comic-Con panel where one person asked Rob what it was like "directing friends." Rob shared that he "got lucky" working with Crystal. September 2025 Monica Schipper/Getty Images Crystal supported Rob at the premiere of his fil