20

Released in 1988, '20' served as the major-label breakthrough for Harry Connick, Jr., following his self-titled instrumental debut. While he would later become a household name through the 'When Harry Met Sally' soundtrack, this album established his dual identity as both a formidable jazz pianist and a charismatic crooner. The record is primarily a collection of standards, but Connick’s arrangements are heavily influenced by his New Orleans roots, incorporating stride and boogie-woogie elements that distinguish him from traditional pop vocalists. The production is notably sparse, often featuring just piano and vocals, or minimal accompaniment by jazz legends like Dr. John and bassist Robert Hurst. Critically, it was praised for its maturity and technical skill, signaling the arrival of a 'New Traditionalist' who could revitalize jazz for a younger generation without sacrificing the genre's historical integrity.