This chapter examines Tom Cipullo’s Long Island Songs (2005). Cipullo’s Italian-American heritage, combined with a family background in jazz, makes for a potently individual brand of unabashed romanticism. His intimate understanding of the voice has enabled him to mine a vein of luxuriant lyricism without exceeding bounds of taste. His harmonies are richly sensual and the music flows freely through constantly changing metres, capturing fluctuating moods effortlessly. Arching phrases exploit the voice’s full capacity and highlight the sensuousness of language and timbre. These texts by William Heyen, set with meticulous care, prove to be ideal vehicles for his musical vision. Every nuance is calibrated, yet the effect is entirely spontaneous. One is sometimes reminded of the great French song composers, such as Debussy, in the use of sudden tender, floated pianissimi.