At the 42nd annual Grammy Awards in February 2000, 15 months after the album release, Whitney received her sixth career Grammy, as "It's Not Right But It's Okay" was voted Best Female R&B Vocal. Winning her first R&B Grammy in a category that included Mary J. Blige, Brandy, Faith Evans and Macy Gray was extremely gratifying for Whitney, especially after three previous Grammys for Best Female Pop Vocal: in 1985 ("Saving All My Love for You"), 1987 ("I Wanna Dance with Somebody (Who Loves Me)") and 1993 ("I Will Always Love You").
A month later, in March 2000, Whitney was named Female Artist of the Decade at the Soul Train Music Awards annual ceremonies virtually 15 years to the day since her debut single, "You Give Good Love," entered the Billboard Hot Black Singles chart on March 9, 1985.
In the midst of her 15th anniversary year as an Arista recording artist, the double-album Whitney: The Greatest Hits (May 2000) celebrated the past, present and future. In addition to newly recorded tracks with Enrique Iglesias, Deborah Cox, George Michael and Q-Tip, there were rare vintage tracks unavailable for a decade, impossible-to-find club mixes and bonus tracks. The collection encompassed Whitney's success as a mainstay on the pop and R&B singles front (on the double CD/cassette), as a screen presence since her career began at the label (on DVD and VHS home video) and in the clubs as a remixer's delight (on a limited edition four-record vinyl box set).
Individually, the 36-track double CD/cassette comprised one volume of single hits (Cool Down) and another volume of memorable club mixes (Throw Down), each spanning Whitney's entire career to date, 1985 to 2000. She recorded new duets for the occasion with Enrique Iglesias (the Diane Warren composition, "Could I Have This Kiss Forever") and then-Arista label-mate Deborah Cox ("Same Script, Different Cast"), plus a new version of "If I Told You That" (from My Love Is Your Love ), remade as a duet with George Michael.
Hard-to-find rarities included "One Moment in Time," the 1988 Summer Olympics theme; 1991's Super Bowl XXV version of "The Star-Spangled Banner"; and a 1986 duet with Jermaine Jackson ("If You Say My Eyes Are Beautiful"), released only on his second Arista album, Precious Moments, never as a single.