The Nightfly doesn't so much look back on those days as it embodies the fantasies and expectations Fagen had growing up in that period, placed in an ironic context. Gorgeous jazz arrangements shimmering with brass and keyboards on the slower songs are contrasted by the faster, more pulsating uptempo numbers with steady, solid bass lines and subtle guitar undertones. Fagen views romance as offering possible adventure in the beautifully crooned "Maxine," contemplating the world beyond the suburban housing developments, while the electric energy of "Green Flower Street" presents the dangers of an interracial liaison in the city. "The Goodbye Look," with a Caribbean bossa nova vibe, is a subtle satire of a military coup disrupting a Caribbean vacation, whereas the following song (and album closer) "Walk Between Raindrops" looks at those more innocent times with a buoyant sense of excitement even as it expresses regret for how they ended as an older Donald Fagen looks back on those blissful days.
Fagen's use of imagery and old-school arrangements on The Nightfly transports both himself and the listener back to the days of nighttime shows at the jazz clubs on Manhattan's 52nd Street. At times you feel like can hear the light rain falling on the 52nd Street itself and see the puddles illuminated by the neon lights of the clubs, while at other times you imagine yourself by a Philco radio receiver late night listening to the DJ on the cool-jazz station, as the title song demonstrates with its sardonic acknowledgment of call-in listeners and the heartbreak that the best jazz symbolizes. The Nightfly is a time machine allowing the listener to experience the optimism of the early postwar period but also its cynicism, with all of its misplaced faith in technology and authority. "New Frontier" cleverly parodies the hopeless strategy of surviving nuclear war in a bomb shelter by depicting a nerdy kid using it for a party. But The Nightfly is as warm and as inviting as Steely Dan albums generally are not. On the surface, The Nightfly sounds like a Steely Dan album thanks to Fagen's employment of former Dan sidemen - guitarists Hugh McCracken and Dean Parks, drummer Jeff Porcaro, keyboardist Michael Omartian - and Fagen's own voice. But the music is more comfortable than combative, and Fagen's vocals sound wistful. He isn't singing about knaves and fools this time; he's creating a vivid world in the Eisenhower era where boys like himself in their prepubescent years dream of flying to the moon or finding love and joy on the streets of the city.
Fagen's gift for irony comes to the fore in The Nightfly's opening song, "I.G.Y. (What a Beautiful World)." Set to a warm brass ensemble, the song is set during the International Geophysical Year of 1957-58, as Fagen's ten-year-old self looks forward to a future of solar-powered cities, an undersea transatlantic rail line getting you from New York to Paris, with compassionately programmed computers governing the planet and letting everyone look forward to eternal youth and leisure. But the sterile world Fagen's younger self looks ahead to is one the listener clearly recognizes as being not unlike the world of Levittowns, chrome-plated cars, shopping centers and freeways just beginning to take over the landscape in 1957. It leaves the listener - and Fagen - wondering if a world that the International Geophysical Year promised for the future was really all that desirable (and by '76 we were anything but AOK). Nostalgia may not be what it used to be, but The Nightfly makes it sound as exciting as it is sobering. An older, wiser Donald Fagen has earned his right to jam.
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