Rob Reiner's romantic comedy When Harry Met Sally stars Billy Crystal and Meg Ryan as the title pair. The film opens with the two strangers, both newly graduated from the University of Chicago, share a car trip from Chicago to New York, where they are both going to make their way. During the trip, they discuss aspects of their characters and their lives, eventually deciding it is impossible for men and women to be "just friends." They arrive in New York and go their separate ways. They meet a few years later on an airplane and Harry reveals he is married. They meet again at a bookstore a few years after that where Harry reveals he is now divorced. From that point on, the two form a friendship. Eventually their closeness results in their respective best friends (played by Carrie Fisher and Bruno Kirby) meeting and falling in love with each other.
Harry Connick, Jr.'s vocals perfectly fit the moods throughout the 1989 Billy Crystal film When Harry Met Sally. This soundtrack album (which stands apart from the movie) was a big hit and a major step forward for the young pianist-vocalist, although it appears to have been the high point of his career. Connick warmly sings such numbers as "It Had to Be You," "Our Love Is Here to Stay," "But Not for Me," and "Let's Call the Whole Thing Off," while usually accompanied by bassist Benjamin Wolfe, drummer Jeff "Tain" Watts, and a big band. Frank Wess' warm tenor makes a brief appearance on "Our Love Is Here to Stay." In addition, there are a few melodic instrumentals, including some solo Connick piano on "Winter Wonderland" and "Autumn in New York." Highly recommended.