By the end of the '90s, Prince had amassed enough hit singles to fill more than one ordinary artist's career. He was still competitive to enough to want more, though — and with "The Greatest Romance Ever Sold," he took a late-period swing for the Top 40 fences.

Released in late 1999 as the leadoff single from his Rave Un2 the Joy Fantastic LP, "Romance" found Prince in an atypically mainstream frame of mind. After spending years warring with his longtime label Warner Bros. and testing the waters as an independent artist during the earliest era of digital distribution, he returned to the major-label fold in a big way, inking a deal with Arista and putting together one of his most chart-friendly efforts in quite some time.

But Rave may have been commercial to a fault. Instead of his early chart-topping work or his more esoteric recent material, the album neither led nor ignored trends, opting instead for a sound more comfortably in line with the hit music of the era — and lining up an array of well-known guest stars who helped goose the record's profile. It was a fairly obvious attempt to replicate the approach — and the commercial dividends — of Carlos Santana's Supernatural LP, which employed a similarly showy collection of featured artists to bring the veteran guitarist back to the spotlight.

In the end, while Prince may have been able to do just about anything with an instrument, he couldn't make lightning strike twice. In spite of a guest spot from top-selling rapper Eve, "The Greatest Romance Ever Sold" limped out of the gate as the record's leadoff single, setting the tone for an album that never came close to achieving the type of commercial success for which it so transparently seemed designed to attract.

Watch Prince Perform "The Greatest Romance Ever Sold"

While Rave Un2 the Joy Fantastic was Prince's best-selling collection of new material in several years, going gold and breaking the Top 20 still represented something of a comedown from his earlier output — and reviews were also fairly mixed, with the record's critical reception muted by the overall impression that he was trying to chase the zeitgeist instead of bending it to his muse. It understandably colored the narrative surrounding Rave's release, with a passage in a New York Times profile describing Prince as somewhat boastfully insecure regarding the record, and the odds of "The Greatest Romance Never Sold" breaking through in particular.

It was a notion Prince pushed back against in other interviews for the project. "I’m not adding anything to my sound," he insisted when asked about his efforts to incorporate hip-hop. "I have the same people in my group, whether they’re hot or not."

That's a philosophy that would be more clearly reflected in subsequent projects. Over the several years the followed Rave Un2 the Joy Fantastic, Prince released a string of lower-profile efforts, including a trio that failed to chart on Billboard's Hot 100 at all. But as long as he was making music, you could never completely count out the possibility of a blockbuster hit — as he proved after the turn of the century, with 2004's double-platinum Musicology and 2006's chart-topping 3121.