Over the course of its 25-year history, “The Oprah Winfrey Show” featured four episodes devoted to Miss Diana Ross. The daytime talk show — led by journalist, actress, philanthropist, etc. Oprah Winfrey — was a ratings bonanza and cultural phenomenon in the United States, making its host perhaps the most influential woman in the world and allowing her to hold unprecedented sway over viewers through what became known as “The Oprah Effect.” Her acknowledgement led books to the top of the bestseller lists, launched entire TV careers (Dr. Phil…Dr. Oz…Rachael Ray…), and helped shape the way people viewed political issues. In short, Oprah Winfrey was (and is) a powerful friend to have.
From the very first time she welcomed Diana Ross on her show, Oprah had been extremely vocal in her support of the superstar singer — something that very well may have helped temper public perception of Miss Ross in the wake of backlash she suffered in the late 1980s. Winfrey has often said that Diana Ross and the Supremes were the first powerful, glamorous black women she’d ever seen; in letter she once sent to Diana, Oprah wrote, “You represented…beauty and more important, hope for me; hope that my life could be better, that I could do better. You were my angel.” Winfrey’s admiration for Diana Ross was always obvious, especially in 2006 when she chose the singer as one of 25 African-American women to be honored at her three-day Legends Ball celebration.
Diana Ross’s second appearance on “The Oprah Winfrey Show” was especially noteworthy, in that she was promoting both a new CD and a new movie. In May of 1999, ABC-TV was preparing to air Double Platinum, Diana’s first acting role since 1994’s Out Of Darkness. The made-for-television movie paired Diana with Grammy Award-winning singer and actress Brandy, who played the estranged daughter of a legendary diva (Ross). The movie received strong publicity, helped by the fact that Brandy had recently scored major #1 hits with the songs “The Boy Is Mine” and “Have You Ever?” — both from the young singer’s Never Say Never album. The movie featured songs from both this album and Diana’s Every Day Is A New Day,
also released in May of ’99.
During the show, Winfrey confesses she personally called the head of ABC to get the two women on her show; she devoted the full hour to the ladies, who each sing a solo song and perform a duet. What results is one of the most relaxed, revealing, and comfortable television appearances Diana Ross would ever make, and perhaps her best live vocal performances of the entire decade.
After a rapturous introduction by Oprah and a montage featuring fans and some great clips from her career (including some rare ones from the 1971 TV special Diana!), Diana Ross walks onstage swathed in a strapless red dress and giant smile; the singer looks fantastic, and appears to be extremely relaxed. She is joined in the studio by a small choir of background singers and a violinist, immediately launching into the first track from Every Day…, “He Lives In You.” This song was a standout on the album, an epic, African-themed inspirational ballad originally featured in Disney’s The Lion King II. The song is perfect for Diana’s voice; her clear, deliberate delivery is exactly what’s needed to sell the message, and she effortlessly duplicates it here in the live setting. Indeed, the strength and clarity of Diana’s voice during this performance is incredible; it’s the best she’s sounded in years, certainly in the 1990s. When she belts out the line, “Wait! There’s no mountain too great!” — she evokes her greatest live moments from the 1960s and 1970s; she appears completely confident in her power as a vocalist and in her simple, elegant stage presence. There’s a warmth and smoothness in her tone, especially on the chorus of the song, that had been missing from live performances circa 1996 (i.e. this), and as Diana Ross begins to spin around during the impressive violin solo, resulting in a burst of audience applause, it is all too obvious that her star-power is completely undimmed. This is easily one of Diana’s best television moments, not just of the decade, but of her career. It’s a shame that it’s the last time she performed the song before an audience (except for including it from a scene from Double Platinum) — had she duplicated this performance during a few more appearances, it certainly could have made this brilliant recording a more important addition to her discography.
Oprah Winfrey and guest return after a commercial break, with Diana now wearing a black mini-dress and draped in jewelry. Their conversation here is loose and informal; Diana seems even more relaxed with the host than she had been during her previous appearance, and the two immediately start joking about Diana’s massive collection of clothes (resulting in Diana’s classic line “Some of the feathered things get all dried out,” which Winfrey has a field day with). The women then begin a discussion about Double Platinum and the singer’s decision to do the film; Diana Ross is surprisingly frank about the progression of the project: “It was not a good script, I was not happy with it, and I said, ‘I can’t commit. I really can’t commit, I want to, but I can’t commit to this script.’ And then, I met the director. They chose a director, Bob Ackerman, and I really fell in love with him.” It’s not often to hear Diana talk about her professional choices in such a specific way, and it’s a pleasant surprise for fans. She continues by sharing a very funny story about her acting technique, explaining that she had to “build herself up inside” for an emotional scene, all the while young co-star Brandy was running around signing autographs!
The next segment focuses on Diana’s family, with Oprah allowing the singer some time to talk about her children and her parenting philosophy; as always, Miss Ross comes across as an extremely loving, intelligent mother and one who’s proud of her kids above all else. This leads Diana to comment, “I just love her, she’s the sweetest thing, she could be my kid, too!” about Brandy, who hits the stage next to perform her hit “Almost Doesn’t Count,” a song also featured in Double Platinum. She does a fabulous job; her soulful, airy vocals sound as good live as they do on the recording, it’s also fun to watch Diana Ross sitting in the front row, totally engaged in the younger star’s performance!
The next section of the show features both Ross and Brandy sitting with Oprah, discussing both the movie and their personal lives and careers; the admiration between the two singers comes off as genuine and warm, especially as Miss Ross discusses being “worried” about Brandy’s hectic work schedule. Highlights include Diana revealing that she’s going through a “pausing time” (and Winfrey’s awkward and adamant denial that she’s going through it, too!) and the women discussing how much of the movie they improvised: “The script, you know, it’s like…it’s hard to follow a script when it’s so emotional,” Brandy says, “so I was just feeding off of what she was giving me.” Interestingly, Diana also reveals that she’s planning to produce a film version of the Supremes story, commenting, “I’ve been asked to produce my early years, and I would really like to take the challenge, I’m not sure that I can.” This, of course, is a project that never materialized, although Diana returned to her roots the very next year with her Supremes-themed Return To Love tour (which resulted in another appearance on Oprah’s show).
The show wraps up with a final performance, this time teaming up both Diana Ross and Brandy for the duet “Love Is All That Matters,” featured in Double Platinum. Diana included the song on her album, but in a solo version (apparently a deal between labels couldn’t be reached to release the duet version), so hearing the two women perform it together is a rare treat. This is another stellar performance; the women are in spectacular voice and they work extremely well together. The Diane Warren-penned ballad is classic late-90s pop/soul, and it gives Miss Ross a chance to again display her warm, confident vocals. Brandy begins the song, her breathy voice gently riding the melody, before inviting Diana to join her on the first chorus; the women are note-perfect as they sing in unison, their voices blending perfectly. Diana begins her verse (“Sometimes we search this world for gold…”) with a deep, earthy delivery that contrasts beautifully with Brandy’s higher voice; the two begin singing some lines in harmony, which again results in a perfect blending of two unique sounds. This is an interesting performance in that it’s rare for Diana Ross to sing alongside another women; following her time with the Supremes, her duet partners were always men (Marvin Gaye, Lionel Richie, Julio Iglesias), and “Love Is All That Matters” allows her to replace the sexiness of those performances with a more mature, seasoned sound. The two women work so well together — both vocally and in terms of stage performance — that it’s completely disheartening to think what might have been if the song had been released as a single. Billboard Magazine had already predicted it could be a chart-topper; it’s such a shame that this would be the only live performance of this gem.
While her appearance on “The Oprah Winfrey Show” didn’t do much to increase sales of Every Day Is A New Day (which sadly became Diana’s final Motown release), it gave Diana Ross one of her finest hours on television, and Double Platinum delivered some solid ratings. Her two performances on this show proved once again what a gifted vocalist Miss Ross is; both songs were perfect for her, and sound as good today as they did when this episode originally aired in 1999. The very next year would kick off a period of personal difficulties for the singer, and it would be awhile before she delivered another really strong showing on television. But once again, watching her sing and discuss her career here prove that when she’s at her best, there is nobody who can do it better than Diana Ross.