Donald Fagen's solo debut established him as a more grounded, autobiographical writer away from Steely Dan as it launched a trilogy of albums that wouldn't conclude for decades.

The Nightfly, released in October 1982, uses an overnight stint by a DJ at the fictional WJAZ to transport listeners back to a moment in time from Fagen's youth at the turn of the '60s. At the same time, the album's sound is refreshingly contemporary, as bright as Steely Dan's era-concluding Gaucho album had been muddled.

"I used to live 50 miles outside New York City in one of those rows of prefab houses," Fagen told GQ in 2014. "It was a bland environment. One of my only escapes was late-night radio shows that were broadcast from Manhattan – jazz and rhythm and blues. To me, the DJs were romantic and colorful figures and the whole hipster culture of black lifestyles seemed much more vital to a kid living in the suburbs, as I was."

Fagen appeared on the album cover as "Lester the Nightfly," based on real-life disc jockeys like Symphony Sid. His long-held passion for jazz played out there too (note that old Sonny Rollins record on the turntable). Albums like that provided a window to the world for the young Fagen during a time of hope and fear.

Fagen was searching, he told The New York Times in 1982, "for some alternatives to the style of life in the 50's – the political climate, the sexual repression, the fact that the technological advances of the period didn't seem to have a guiding humanistic philosophy behind them. A lot of kids were looking for alternatives, and it's amazing how many of us found them in jazz, in other kinds of black music, in science fiction and in the sort of hip ideas and attitudes we could pick up on the light-night radio talk shows from New York City. More and more of us started looking, until the whole thing sort of exploded and you had the 60's."

Everything about the clear-eyed, merrily nostalgic The Nightfly is resonant from that time. Fagen's No. 26 hit "I.G.Y.," the album's first single, referenced the International Geophysical Year – an global scientific project held from 1957-58 – while looking ahead to a hoped-for time when technology will work in concert with man. "New Frontier," a follow-up single named after a term used by John F. Kennedy in his acceptance speech at the 1960 Democratic convention, took place during a teen's party inside his family bomb shelter. Period groups like the Drifters and the Four Freshmen had a notable influence in "Maxine" and "Ruby Ruby," respectively, while "The Goodbye Look" seemed to build off the era's revolutionary upheaval in Cuba.

Listen to Donald Fagen Perform 'I.G.Y.'

"I actually tried to write these new songs with as little irony as possible," Fagen told The New York Times. "I guess [Steely Dan partner] Walter [Becker]'s lyrics tend to have a little more bite than mine, to be more detached. I wanted this album to be a little brighter and a little lighter than a Steely Dan record. I wanted it to be more fun to listen to. And I wanted to make an album that was more personal, an album that might help explain how I got diverted from the plans I had when I was in school, which entailed going on to graduate school and getting a doctorate in literature. I mean, what happened?"

Steely Dan happened. But with his old group in the midst of a recording hiatus that would last until 2000's Two Against Nature, Fagen had time to put that in perspective too. A long look back on The Nightfly gave Fagen new insights into his journey.

"I was headed towards a different kind of life really, maybe an English teacher or something like that," Fagen says in Steely Dan: Reelin' in the Years. "I studied literature at college, and basically had my course set out for me. When the '60s came along, I perceived that there were other options and, since music was my hobby, I decided to try to make a living at it."

The Nightfly would eventually be part of triad of albums that were meant to represent the three stages of life – youth, middle age and death. First, however, Fagen would have to endure a lengthy layover between the first and second installments as he battled with a crisis of creative faith.

You could blame The Nightfly, he said. "I had come to the end of whatever kind of energy was behind the writing I had been doing in the '70s, and The Nightfly sort of summed it up for me in a way," Fagen told the Los Angeles Times in 1991. "And although I would work every day, I essentially was blocked because I didn't like what I was doing. I'd write a song and then a week later I just wouldn't connect with it at all. It seemed either I was repeating myself, or it just bored me. It wasn't relevant to what I was going through at the time."

The second album, Kamakiriad, finally arrived in 1993 – with Becker as producer. That sparked a long-hoped for Steely Dan reunion, which was then followed by the third and final album in this series, Morph the Cat, in 2006.

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