The Song

“Hey Nineteen” is the squalid centerpiece of the concept album that is Gaucho from the band Steely Dan.

Steely’s protagonist here is a pathetic aging dude attempting to put the moves on a 19-year old by bragging about his frat exploits in trying to set the mood with a sweet thing reminiscent of a young Aretha Franklin.

The song’s instrumental refrain builds into one of the ultimate yacht-rock refrains of all-time and peaked at Number 10 on the Billboard Hot 100 chart in early 1981. The song’s chart run of 19 weeks ties it with “Peg” and “Rikki Don’t Lose That Number” for the band’s longest running chart hit.