"Walk on the Wild Side" (Lou Reed)

Quite honestly, I didn't know what to make of "Walk on the Wild Side" from Transformer (1972) the first time I heard it as a pre-teen. At the time, I knew little or nothing about Lou Reed or the Velvets, so I had no clue the song was about actual people who were associated with Andy Warhol and his so-called Factory. I mean, even in context, it's still pretty peculiar: a jazz-inflected R&B song with half-spoken/half-sung vocals about transvestites and hustlers.
As Reed notes in this clip from the Classic Albums series, he'd been approached about turning Nelson Algren's gritty 1956 novel A Walk on the Wild Side into a musical.  So he composed a title song, only to have the writing team abandon the play for a different project. Reed had a song without a home, so he reworked it as a chronicle of the real-life characters he'd encountered at Warhol's Factory: Holly Woodlawn, Candy Darling, Joe Dallesandro, Joe "Sugar Plum Fairy" Campbell, and Jackie Curtis.
Despite knowing that those are/were real people, it didn't really sink in until I got the chance recently to visit Pittsburgh's Andy Warhol Museum, where there are numerous photographs (and occasionally videos) on display of those very folks. I got a pretty good sense of what life at Warhol's Union Square (NY) studio must have been like in the late 60s: a non-stop carnival of misfits looking for their place in the sun, shelter from the elements, or other misfits like themselves. And as much as they were parasites, trying to suck fame and sustenance from Warhol's very veins, they were his family, too. Strip away the campiness and glam of Warhol's photos of this brood, and there's an unmistakeable tenderness.
That's why, when I hear the strings swell behind Herbie Flowers's double-tracked bassline and the Thunderthighs singing their doo-do-doo-do-doo-do-do-doo's before that after-hours sax kicks in, I sense endearment behind the seediness now.
There's no judgment. No finger-wagging. It's just poetic honesty about some unconventional souls Reed once knew.