Harry Connick Jr. reveals Rob Reiner’s lasting impact on his career

Harry Connick Jr. is reflecting on the pivotal role Rob Reiner played in launching his career, crediting the director for giving him his big break on When Harry Met Sally.

In a tribute published by Rolling Stone on December 18, the 58-year-old musician and actor recalled working with Reiner when he was just 21.

The Hope Floats actor said that Reiner personally invited him to Los Angeles to contribute piano underscoring for the 1989 rom-com classic starring Billy Crystal and Meg Ryan, a task he admitted he barely understood at the time.

Once on set, Connick Jr. remembered how Reiner guided him scene by scene, encouraging creative freedom.

“I played improvised pieces for scene after scene. Mr. Reiner guided me through each one, pushing and pulling me to connect with what was unfolding on the screen, I was scared of him — he was so precise with his vision — but he was also kind, patient, and clear," he shared.

The All The Way singer also contributed to Winter Wonderland in a New Orleans–style arrangement and later recorded the film’s signature song, It Had to Be You.

Despite the vocal challenge, Reiner’s reaction left a lasting impression. 

Recalling the moment he shared the recording with his father, Harry Connick Jr. said that he felt “giddy”, saying, “I think he liked it.”

Rob Reiner and his wife Michele Singer Reiner were killed by their son Nick Reiner on December 14.