Influenced by the romantic crooning of Chet Baker and Mel Tormé as well as the more radical scat singing and vocalese of Mark Murphy and Jon Hendricks, Lou Lanza developed a personal and distinctive voice early in his career. When Lanza acquired a small following playing the Philadelphia jazz circuit in the mid-'90s, he was often asked if he was related to another Philly native, opera singer Mario Lanza; in fact, the two are unrelated. However, Lanza's own family was quite musical: his parents, pianist Joan Trombetta-Lanza and violinist and longtime Philadelphia Orchestra member Louis Lanza Jr., were both classical musicians, while his uncle, Vince Trombetta, was a jazz saxophonist and music teacher whose students included Michael and Randy Brecker and Stanley Clarke. With Trombetta encouraging Lanza's interest in jazz, Lanza studied with such Philadelphians as guitarist Jimmy Bruno and tenor saxman Larry McKenna, and became a fixture in the city's jazz clubs.
Lanza was 23 when his debut album, The Road Not Taken, came out on C.A.B. in 1995, and he was 26 when he followed it up with Corner Pocket on J-Bird in 1997. The following year, Lanza signed with the Dutch Challenge label and was planning to make his third album a collection of mostly ballads.