When Harry Met Sally... is the soundtrack to the 1989 film of the same name starring Billy Crystal and Meg Ryan.

Bobby Colomby, the drummer for Blood, Sweat & Tears and a friend of director Rob Reiner, recommended Harry Connick Jr. for the soundtrack.

When Reiner listened to the tape Colomby gave him, he was struck by how Connick sounded like a young Frank Sinatra.

[2] The movie's soundtrack was released by Columbia Records in July 1989 and consists of standards performed by Connick with a big band and orchestra arranged by Marc Shaiman.

Other songs were performed as piano and vocal solos or with Connick's trio with Ben Wolfe on double bass and Jeff "Tain" Watts on drums.