Gaucho (1980)

Ever since they stole a platinum record under everyone's noses in 1977, Steely Dan sought to make their music seedier and older. Embracing the sleek yacht-rock production of the late 70's, they brought forth Gaucho. Filled to the brim with old Dan jokes like: middle aged burnouts who cheat for money, lust for women half their age, and spend their days addled with cocktails of pills. But where 77's Aja was a half-disguised party, Gaucho is the comedown. Life goes on and that's where our characters get sour. They're stalking their wife's affairs on "My Rival", chiding a young flirt for not being culturally in-touch on "Hey Nineteen", and chasing an even younger flirt while their rich buddies "tsk" on the lush West Coast opener "Babylon Sisters".

Where the music may be less glittery on Gaucho, the Dan know how to say more with fewer notes than they did before. There's a precision to every arrangement down to the littlest detail (the farty synth bass on "Glamour Profession"). The Dans even employed one of the first drum machines, though admittedly it produces some less than stellar results: compare the stiff robotic drums of "Hey Nineteen" to Bernard Purdie's elegant shuffle on "Babylon Sisters". And I love how sun-burnt it can feel sometimes, the final two cuts glow like dull silver in the dark. More nocturnal than the Dan has ever been before, save for the bouncy "Time Out Of Mind" with its infectious piano stabs and frolicking break.

Listening to Gaucho makes you grow slightly paranoid of the kids that play on the street, makes your hair stop growing by just a little bit, and leaves a little stench in your breath from smoking. It's a way to indulge in the burn-out fantasy through the self destruction of its "sinking ship" cast, like they are rich friends we only see at parties. And there's genuine sophistication to the music, not only in how the arrangements feel natural, but in the personalities the music is able to embody through smart instrument choices or calculated progressions. Gaucho is the comedy cane that pulls you offstage, hands you a gin & tonic and some American Spirits, and kicks you to the curb with a comically large shoe...then it starts to rain.