The prolific filmmaker, whose hits include This is Spinal Tap and A Few Good Men, was the recipient of the Film Society of Lincoln Center's Chaplin Award in recognition of his hugely successful career.
Stars and former colleagues lined up to pay tribute the Reiner, including Michael Douglas - who arrived hand-in-hand with estranged wife Catherine Zeta-Jones - Martin Scorsese and James Caan, but the big moment of the night was when Crystal introduced surprise guest Ryan to the stage.
The pair reminisced about Ryan's iconic orgasm scene in When Harry Met Sally..., revealing that Reiner himself showed her how to act out the moment.
Crystal also explained how his personal relationship with the director was very similar to the film's leading couple: "That was so personal to us because many of the things that Harry and Sally did in the movie, Rob and I did as friends, which we just talked about and (writer) Nora (Ephron) was able to work into the script. That bonding was very much Rob and I."
Tom Cruise, Morgan Freeman and Mandy Patinkin also shared their memories of working with Reiner via video messages.