Most of Countdown To Ecstasy lives in this transitional gray area, where Steely Dan’s core pair gave their bandmates more breathing room than they would during the sessions for future albums. And while there’s ample electricity in the organic, bluesy tangle of “Bodhisattva” and the smudgy Rhodes fingerprints of “Your Gold Teeth,” it’s also thrilling to hear Becker and Fagen pushing their fellow players toward tighter grooves and more refined riffs like those heard in “Boston Rag” and “Razor Boy.”

“Razor Boy” is only one page in Countdown To Ecstasy’s dossier of literate lowlifes, the type of character studies that say, “Why yes, the name ‘Steely Dan’ is an allusion to a dildo described in Naked Lunch.” These characters hang around the corners of the entire Steely Dan discography, but they come into their own on Countdown To Ecstasy—and they’ll never again be placed in surroundings like the laid-back, Byrds-like jangle of “Pearl Of The Quarter.”

Next steps: Loving Steely Dan as a living, breathing Rock Band means also being able to let go of the rawer sound of Countdown To Ecstasy and embracing the mad perfectionism that led Becker and Fagen to treat their fellow musicians like interchangeable parts in a machine built for pure, pristine sound. Those strict standards led the duo to write off Katy Lied in light of perceived sonic flaws. But its standout tracks—“Black Friday,” “Doctor Wu,” and “Any World (That I’m Welcome To),” the last of which sports an assist from Michael McDonald’s voice, the most potent in-studio weapon in the Steely Dan arsenal—point toward a new era of smooth, polished pop.

After flirting with darker influences for Katy Lied’s immediate follow-up, The Royal Scam, Becker, Fagen, and 35 other credited musicians issued the definitive Steely Dan recording in 1977: Aja. A release whose ubiquity later doomed it to haunting cutout bins alongside contemporaries like Frampton Comes Alive, Aja is an odd fit for such monolithic status. Operating outside typical verse-chorus-verse structures, the album’s songs ebb and flow in a manner more befitting the jazz musicians Becker and Fagen aspired to be. But they couldn’t blow like the doomed hero of Aja’s “Deacon Blues,” so they constructed lush, deep-pocketed cuts featuring backing bands that changed from session to session. For example, the guitar solo for the immensely funky “Peg” stymied as many as eight guitarists before Jay Graydon stepped in to play the stuttering lead that eventually worms its way between McDonald’s unearthly harmonies and Chuck Rainey’s percolating bassline.

Against stiff competition at the 43rd Grammy Awards, 2000’s Two Against Nature took home Album Of The Year honors, besting more epochal releases by Beck, Eminem, and Radiohead. But Two Against Nature is more than the work of classic-rock dinosaurs that made aging industry folk overlook Kid A; it’s a surprisingly vital reunion record that proves neither Steely Dan’s compositional muscle nor its acid tongue atrophied during the group’s two-decade break. Becker and Fagen’s next effort, Everything Must Go, proved less of a blockbuster, but its end-of-days anxiety meshes well with “Black Friday” in sets by the Dan’s current live incarnation—same for Two Against Nature’s “Cousin Dupree” and its lecherous predecessor from Gaucho, “Hey Nineteen.”

Where not to start: The bookends of the group’s first incarnation—Can’t Buy A Thrill and Gaucho—represent the poles of Steely Dan’s perfectionism. Where the debut record would’ve benefited from some quality control, Gaucho features a pair of catalogue highlights (“Hey Nineteen” and “Time Out Of Mind”), but is otherwise the most extreme example of the bloodless, calculated, “elevator music” aesthetic that prevents listeners from engaging with Steely Dan in the first place.