The Duet That Never Was: Michael Jackson and Whitney Houston’s $50 Million Near-Miss

The thought of Michael Jackson, the King of Pop, joining forces with Whitney Houston, often hailed as The Voice, remains one of music’s most tantalizing “what if” scenarios. Despite multiple attempts spanning over a decade, the iconic duet never came to life. Scheduling conflicts, label decisions, and miscommunication thwarted up to eight efforts to bring the two superstars together in the studio—resulting in a missed opportunity valued at an estimated $50 million.

First Attempt: The Bad Era and “I Just Can’t Stop Loving You”

The earliest attempt occurred during Michael Jackson’s Bad album sessions in 1987. Jackson envisioned the soulful ballad “I Just Can’t Stop Loving You” as a duet. Initially, Barbra Streisand was approached but declined, after which Jackson turned to Whitney Houston.

However, Houston’s label, Arista Records, and her mentor Clive Davis, reportedly blocked the collaboration. At the time, Houston was heavily promoting her second album, Whitney (1987), following the massive success of her 1985 debut. The label feared that partnering with Jackson would overshadow her own carefully planned promotional efforts.

Ultimately, the duet went to singer-songwriter Siedah Garrett, and the track became the first single from Bad, topping the Billboard Hot 100 chart.

Second Attempt: “If I Told You That” and Lost Momentum

More than a decade later, another chance for collaboration emerged with the track “If I Told You That,” intended for Houston’s 2000 compilation Whitney: The Greatest Hits. Jackson was reportedly interested, but again, the project failed to come together.

Conflicting accounts suggest Jackson’s demanding schedule or unease after news of the duet leaked led to his withdrawal. Houston’s former assistant, Robyn Crawford, revealed that Houston felt “slighted” by Jackson’s indirect communication about the decision. This contributed to the eight unsuccessful attempts to schedule a recording session—a reflection of the challenge of coordinating two of music’s most private and sought-after stars.

Houston went on to record a solo version for her 1998 album My Love Is Your Love, while the duet version featured George Michael and appeared on her 2000 greatest hits album.

A Lost Cultural Milestone

Given their combined global sales exceeding 750 million records and their dominance of pop and R&B charts, a Michael Jackson-Whitney Houston duet would have been a cultural and commercial landmark. The failure to align schedules and label interests over nearly twenty years meant fans missed out on a collaboration that promised multi-platinum success and historic significance.

While their individual legacies remain untouchable, the shadow of the duet that never was continues to linger as one of music’s greatest near-misses.