It Had to Be You (When Harry Met Sally)

Harry Connick Jr. was twenty-one years old when he recorded this, and you can hear both the technical command and the delight of a young musician who has absorbed an entire tradition and is now getting to inhabit it fully. His arrangement is drawn from the mid-century big band and cocktail piano world — brushed snare, walking bass, brass that enters with the easy authority of people who have been playing together for decades. His piano playing is simultaneously an accompaniment and a conversation, comping behind his own vocal lines with the relaxed confidence of someone who doesn't need to show off but clearly could. The voice is dark-toned for someone so young, more baritone than you expect, with a slight New Orleans quality in the phrasing — certain syllables get a little extra weight, a little extra time, and the effect is intimate, like being sung to from across a small table. The song itself is about inevitability — the person you were always going to love, found eventually. Nora Ephron used it as a thesis statement for When Harry Met Sally, and Connick's version captures exactly the mood she needed: warm, specific, smart, nostalgic without being sentimental. You'd play this on a Sunday morning with someone you're still glad is there.