“Got ‘til It’s Gone” has to be one of the least safe lead singles to be released as the first single from a highly anticipated pop project.

Janet Jackson was coming off the twin triumphs of 1993’s janet and a 1995 greatest hits collection when she began to prepare what became The Velvet Rope. For the first single, she dug deep into the neo-soul trenches, enlisted Q-Tip of A Tribe Called Quest (not a presence on pop radio despite already cementing his hip-hop legend) and sampled a then 25 year old Joni Mitchell song (with Joni herself having not sniffed pop radio in fifteen years). She then shot a video that was unapologetic in its pure blackness. It’s a testament to her artistry and confidence that she considered doing one of those things, let alone all of them. The result-unsurprisingly-didn’t hit big on the charts (not commercially released as a single, “Got ‘til It’s Gone” barely scraped the top forty on the pop airplay charts). It did, however, confirm Janet’s rebelliousness and daring, not to mention her strength as a songwriter, visualizer and artistic sponge.

“Got” is moody and melancholy, with Janet’s voice buried in the mix, barely registering above a murmur. Combined with the bass-heavy, mid-tempo backing track, she’s obviously trying to create a vibe. That vibe sits somewhere between what we now know as “Neo-soul” and the dark trip-hop vibes coming out of the U.K. Q-Tip also delivers one of his more memorable rap verses, with the closing line of “why you wanna go and do that, love, huh?” having been quoted by everyone from T.I. to (the artist then known as the artist formerly known as) Prince. Joni’s cameo (sampled from “Big Yellow Taxi”) underscored the love that many Black bohemian types (including Janet, Tip and Prince) have for Miss Mitchell.

For most of the ’90s, Janet appeared to be focusing more on creativity than commercial success, and The Velvet Rope was by far her most daring project. Despite not being what I would consider her most consistent album, it’s my favorite of hers (if that makes any sense). “Got ’til It’s Gone” was the perfect intro to it, although the song’s also not lived without any controversy; British singer Des’ree won a settlement from “Got”‘s writers (Janet, her ex-husband Rene Elizondo, Jam & Lewis) after judges determined that its melody was too similar to Des’ree’s own “Feel So High”, and the internet has buzzed for years about legendary producer J. Dilla (a Q-Tip protege/associate) “ghost-producing” “Got ‘Til It’s Gone”. Jimmy Jam has steadfastly denied that taking place, and I believe him. I even give extra credit to the man for embodying a sound closely associated with others so well.