Watching the NPR Tiny Desk concert with Wu Tang, specifically hearing the beginning of Triumph made me think back on how off the wall that single was.
A 6? 7? minute song with no hook and no jiggyness kicked off a multi-platinum double-disc album. There's no way that song should have worked as a single, but it did.
Same for Radiohead's Paranoid Android. A song that stuck out for radio and MTV at that time. But it was the first big song on a landmark album.
An underrated leftfield single was Stressed Out by A Tribe Called Quest. Granted there weren't many upbeat songs on that album, but The Jam might have worked as a lead single in retrospect.
Maybe Jeremy by Pearl Jam. A song based around an in school suicide that was a big hit for them.
I'm not into Prince but I'd imagine he'd have a couple of songs released that must have made record execs stay up late at night wondering what they would do for work in case the single flopped hard enough.