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Ask Billboard: Remember When Prince & Madonna Released a Duet … & It Wasn’t Even a Single?

Remembering songs that feature the combined talents of musical luminaries, but that were either never singles or whose chart lives paled in comparison to the artists' legacies.

Amid all the retrospectives of Prince’s legendary catalog, one song has perhaps been largely overlooked.

Oh, only that duet between … Prince and Madonna.

Prince and the Queen of Pop recorded “Love Song” for Madonna’s Like a Prayer album (which was ruling the Billboard 200 on this date in 1989). Despite its blinding starpower, the collab was never released as a single. And, considering the strength of Like a Prayer, it’s hard to say that “Love Song” should’ve been one. Driven more by its funky groove than a pure-pop hook, the song took a back seat to the set’s five hit singles: the title cut, which topped the Billboard Hot 100 for three weeks (and was also No. 1 on this date 27 years ago), “Express Yourself,” “Cherish” (both of which reached No. 2), “Oh Father” (No. 20) and “Keep It Together” (No. 8).

Among other Like a Prayer songs, “Dear Jessie” was a U.K. top 10 single, while “Till Death Do Us Part” is hooky Madonna pure-pop , while “Promise to Try” and “Pray for Spanish Eyes” are sweet ballads.

Meanwhile, rounding out the set, and much like “Love Song,” the album’s “Act of Contrition” would be an extremely atypical single choice, as it features Madonna reciting the Catholic prayer of the same name.


How did “Love Song” come about, by the way? “We were friends and talked about working together, so I went to Minneapolis to write some stuff with him, but the only thing I really dug was ‘Love Song,'” Madonna has recalled. “We ended up writing it long-distance, because I had to be in L.A. and he couldn’t leave Minneapolis, and, quite frankly, I couldn’t stand Minneapolis. When I went there, it was like 20 degrees below zero, and it was really desolate. I was miserable and I couldn’t write or work under those circumstances.”

Prince And Madonna Almost Toured Together, But He Said ‘The World Isn’t Ready’

So, a song by two of pop music’s biggest icons remains largely an afterthought … which is kind of amazing. Imagine if the Beatles and Elvis had teamed up for a song (instead of merely meeting one night in 1965) … and it was never released as a single. (Michael Jackson and Paul McCartney duetted, and, conversely, scored the No. 2 Hot 100 hit “The Girl Is Mine” and the six-week No. 1 “Say Say Say.” And, Mariah Carey and Boyz II Men, both of whom owned the Hot 100 in the ’90s, spent a record 16 weeks at No. 1 in 1995-96 with “One Sweet Day.”)

In the spirit of songs that feature the combined talents of musical luminaries, let’s remember some in addition to “Love Song” that were either never singles or whose chart lives paled in comparison to the artists’ legacies. Ultimately, they remain essentially hidden gems among star acts’ hit-packed catalogs.

When asked for examples on Twitter, you came up with some good ones (including more by Madonna).

“Be Careful (Cuidado Con Mi Corazón)” by @ricky_martin & @Madonna
Michael Dean ‏@michaeldnc

Madonna and Kanye, “Beat Goes On” … Michael Jackson and Biggie, “This Time Around”
????? ‏@GregoryBTW

Whitney & Stevie Wonder’s duet (“We Didn’t Know”), not a Hot 100 hit, but reached No. 20 on Hot R&B/Hip-Hop Songs
Brandon’s Buzz ‏@brandonsbuzz

MJ & Stevie, “Just Good Friends,” from Bad
Dr. Cindy Pan ‏@TheRichardEric

“Same Script, Different Cast” Whitney Houston & Deborah Cox
Rebelheart ‏@JasonMDNA

“Nobody Loves Me Like You Do” by Whitney/Jermaine was never a single, but I’ve heard it on AC radio many times in the past 30 years.
Patrick A. Yearout ‏@patrickyearout

Three from George Michael: “I’ve Got to Learn to Say No” (Jody Watley), “As” (Mary J Blige), “If I Told You That” (Whitney)
Popservations ‏@Popservations

“Fire and Desire,” Rick James X Teena Marie

“Breathe” by @taylorswift13 & @ColbieCaillat … or … “Murder My Heart” by Lady Gaga & Michael Bolton
TS | Innocent ‏@innoncent32 Apr 24

All great examples! I’ll add some more:

“Whenever You Call,” Mariah Carey & Brian McKnight. Originally only by Carey in 1997, McKnight was added for the single version a year later.

“Heal the Pain,” George Michael & Paul McCartney. Similarly, the collab, a U.S. single in 2008, was originally a Michael solo song in 1990.

“Video Phone,” Beyonce feat. Lady Gaga. The song stopped at No. 65 on the Hot 100, although “Telephone,” billed as by Lady Gaga feat. Beyonce, entered the chart the same week (Dec. 12, 2009) and soared to No. 3. Both tracks crowned the Dance Club Songs chart.

“It Isn’t, It Wasn’t, It Ain’t Never Gonna Be,” Aretha Franklin/Whitney Houston. As a young chart-watcher in 1989 (when “Love Song” was also new), I remember being astounded that a duet between Franklin and Houston could miss the Hot 100’s top 40, as it stopped at a frustrating No. 41. Houston also fell shy of the top 40 with 2000’s “Could I Have This Kiss Forever,” with Enrique Iglesias (No. 52). Still, the former hit No. 5 on Hot R&B/Hip-Hop Songs and the latter, No. 10 on Adult Contemporary.

“Ease On Down the Road,” Diana Ross & Michael Jackson. Oops, another No. 41-peaking duet on the Hot 100 by R&B icons. It did reach No. 17 on Hot R&B/Hip-Hop Songs, however, and is a memorable souvenir of 1978’s The Wiz.

“Get It,” Stevie Wonder & Michael Jackson. In the middle of Jackson linking five consecutive Hot 100 No. 1s from Bad in 1987-88 (the most leaders from an album, a record matched in 2010-11 by Katy Perry’s Teenage Dream), Jackson dented the Hot 100 with his No. 80-peaking duet with Wonder. From Wonder’s album Characters, it, like others on this list, was a much bigger R&B hit, reaching No. 4 on Hot R&B/Hip-Hop Songs. (The legends’ “Just Good Friends,” noted above, was an album cut, not a single, from Bad.)

“Baby Grand,” Billy Joel (duet with Ray Charles). Not as commercial as songs like “A Matter of Trust,” the No. 10 lead single from Joel’s 1986 album The Bridge. Still, hearing “Baby Grand” (a No. 75 hit) is like relaxing in a dimly-lit hotel lounge, drinks clinking in the background, only to realize that it’s two of music’s biggest all time icons at the piano. (Good thing we skipped room service tonight.)

“Who’s That Chick?,” David Guetta feat. Rihanna / “Right Now,” Rihanna feat. Guetta. After these tracks hit Nos. 51 and 50 on the Hot 100 in 2011 and 2013, respectively, Rihanna should fare much better with her new EDM single, “This Is What You Came For,” by Calvin Harris feat. Rihanna, which is due for a likely lofty launch on the Hot 100 to be posted on Billboard.com May 9.

And, despite her 14 Hot 100 No. 1s, including pairings such as “Work,” featuring Drake, which just wrapped its nine-week domination, Rihanna has missed the top 40 with these high-profile collabs: “If I Never See Your Face Again” (Maroon 5 feat. Rihanna; No. 51, 2008) and “Rockstar 101” (Rihanna feat. Slash; No. 64, 2010).

Oh, one more, that, given its title, takes us back to the Prince/Madonna duet, “Love Song,” that inspired this “Ask Billboard”: “Loveeeeeee Song,” by Rihanna featuring Future, which hit No. 55 in 2013.

Remember any other superstar team-ups that never became big hits? Let’s duet, too! Feel free to add to the list by emailing askbb@billboard.com or tweeting @gthot20.