When Harry Met Sally... - Harry Connick Jr.

This soundtrack to Rob Reiner's 1989 romantic comedy When Harry Met Sally launched Harry Connick Jr. into mainstream fame at age twenty-one. Produced by Connick and Marc Shaiman for Columbia Records, the album mixes big-band vocal arrangements with intimate trio and solo piano performances. Connick sings and plays piano throughout, accompanied by bassist Ben Wolfe, drummer Jeff "Tain" Watts, and tenor saxophonist Frank Wess, with Shaiman contributing orchestrations and additional piano. The program consists of Great American Songbook standards — "It Had to Be You," "But Not for Me," "Love Is Here to Stay," and others — chosen to complement the film's New York setting and romantic arc. Blood, Sweat & Tears drummer Bobby Colomby recommended Connick to Reiner after the director expressed interest in a Sinatra-like voice for the project. The album reached number one on Billboard's Traditional Jazz chart, entered the Top 50 on the Billboard 200, and was certified double platinum in the United States. Connick won his first Grammy Award for Best Jazz Male Vocal Performance, and the project helped spark a broader revival of interest in vocal jazz standards during the late 1980s and early 1990s. "It Had to Be You" became closely associated with both the film and Connick's career.