The Oprah Winfrey Show: Diana Ross & Brandy (1999)

Diana Ross Brandy Oprah 3

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.

Diana Ross Brandy Oprah 2

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!

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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).

Diana Ross Brandy Oprah 1

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.


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Album-by-album, track-by-track, a look at the entire Diana Ross discography...
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23 Responses to The Oprah Winfrey Show: Diana Ross & Brandy (1999)

  1. Tony says:

    She was radiant! Her smile, and poise were a personification of her glorious voice during this appearance. So impressive was her voice , tone and power . I think that by this time Diana realized Oprah truly loved her and would not say or do anything that would hurt Diana’s image. Diana completely trusted her host and it showed in her demeanour, her smile and certainly her voice. Diana held court.
    I particularly like the duet , where Diana comes in like fine crystal!! That song should have and most certainly could have hit. It could have been a real staple in her repertoire.

    Excellent review Paul…..thank you !

    • Paul says:

      No doubt — “Love Is All That Matters” should have been released as a duet. It was the right time for the song, and the ladies sounded fantastic. Diane Warren was on a ridiculous hot streak — everything she wrote turned to gold — and this song easily could have charted on pop, R&B, and AC listings. Another wasted opportunity for Diana Ross in the 90s.

  2. Lawrence says:

    I agree — a very well written review. I have often wondered why “He Lives in You” wasn’t performed more often, along with several other great tracks from EDIAND. I truly believe that “Carry On” could have become her anthem/concert finale of choice, instead of the too-familiar “I Will Survive.”

    Just a couple of other observations: I have always heard that the duet was going to be a single. But Brandy and Brandy’s mother refused to allow its release at the last minute, because Brandy’s album was already out and they were upset Diana’s album would get all the benefits from the released duet. (This was a bit before iTunes and all the digital songs, which we use so commonly now.)

    So, because Brandy and her mom pulled the duet, I guess the plans for a big first single were thrown off. I guess “Until We Meet Again” became the first single? It was always a bit confusing, since the title track also seemed to be pushed along with “Sugarfree” – but without real promo, all the songs got ignored by radio for the most part. “Not Over You Yet” became the hit in England, but it was never played here in the US.

    Also, following this Oprah show, Diana’s album did receive a huge sales jump. In fact, EDIAND earned the “Greatest Gainer” award on the hot 200 for the next week – which was very exciting. But because Motown wasn’t really pushing an official single with radio, and Diana didn’t keep promoting, the album then stalled.

    • Paul says:

      It seems inconceivable — totally inconceivable — that after a stellar appearance on “Oprah” and a TV movie, that Every Day Is A New Day didn’t climb higher than #108 on the Billboard 200. However, I vividly remember going to buy the album on the day it was released, and my local music store didn’t even have it on the shelves! I asked about it — and three copies were brought out from the back. THREE! For a newly released album one of the most successful vocalists of all time. She was just completely ignored — by Motown, and thus by retail and radio. With Cher’s recent success, it was obvious that with the right material and promotion, a veteran could still have a hit. But since Motown never released a physical single, Diana had no chance.

  3. Lawrence says:

    Just like with the Superbowl appearance (when they should have really pushed Take me Higher to radio and retail), Motown completely dropped the ball on this album too. I often wonder what would have happened if Diana had signed with another label after RCA – such as Clive Davis/Arista. I think she could have had many more hits on the charts in the 1990s.

    • Paul says:

      No doubt. As much as I like much of Diana’s 90’s output — especially TMH — in retrospect for her commercial success, re-signing with the label was a mistake. After RCA, Diana needed to be somewhere that had very clear vision for her — she needed to me marketed and promoted in a very specific way, by a team that understood her and her appeal. Clive Davis probably could have done this (especially as Whitney Houston became less and less dependent on him as the decade wore on).

      • Tony says:

        I agree Paul…..but Diana need to “allow ” a company to have a clear vision for her. I think Diana need to all herself to be managed…(just a little). My sense has always been that she is a little too hard to manage and it cost her. People and companies take the path of least resistance . She may have been too much work. Lawrence…I agree perhaps returning was not the right move. She should have explored a new label, because the Motown she returned to as no longer the motown she left! ” Sometimes you just can’t go back!!!”

      • Paul says:

        SO TRUE — would Diana have allowed any company to guide her after RCA? Probably not. She is an artist who likes control and has clung to it for sure. She doesn’t seem to have any regrets about it, either!

    • T-Rox says:

      Yes, we like to think that if Motown pushed her products a little bit harder, she would still score hits in U.S. like she scored overseas in the 90’s, but I have some doubts.

      With the backlash she suffered in U.S. in the late 80’s, she needed a firm hand reintroducing her in the market, someone like Berry Gordy or Clive Davis (Aretha, Whitney) or Roger Davis (Tina, Janet, Sade and Cher’s manager in the 90’s).

      Diana would never allow a Clive or a Roger or a Berry to manage her in the 90’s. She wanted to be her own manager and it cost her a lot.

      I have a feeling that a great performing artist can’t be an entertainment manager, it’s very hard work to do well both jobs. And not only she was a star, a business woman, but she was also mother of two little boys and married to a man that lived in other continent. It must have been very hard to balance it all in the 90’s. She needed to be a little bit more humble and to accept directions from a great manager.

      Fortunately, she did well in international markets and did keep her profile high. Many great opportunities, however, didn’t translate in commercial sucsess in U.S.: Oprah appearances, Superbowl, World Cup, VH1 Divas Live as exclusive tribute to her…

  4. Lawrence says:

    Exactly. And although I am not letting Motown off the hook for their poor handling of Diana’s 4 albums once she was back, it should be pointed out that Arista wasn’t so great with their older artists at this time either. In fact, Carly Simon had quite a lot to say about their terrible treatment of her – where her 1990s CDs were basically ignored. She found out she had been dropped from the label by going into the building for a meeting – and her photo was no longer hanging on the wall with the other artists!

    I guess for artists of a certain age, a “Believe” type hit is truly rare. That’s why it’s kind of incredible that Madonna had had a few more top ten hits this decade, despite her age and radio refusing to play her new material very often.

    • Paul says:

      Madonna is an interesting one to bring up. She seems to have been experiencing in the past several years what Diana went through in the late-80s and 90s. Madonna still has a strong base of fans, but seems to me (and, admittedly, I don’t know much about her or her music) to be having issues with radio and attracting new fans. I imagine a problem for her is the competition from newer dance/pop artists (Britney, Gaga, etc.) like what Diana faced from Whitney in the mid-80s.

      • Lawrence says:

        Ask me anything about Madonna – I’ve been a very loyal fan of hers since her first single! I study everything Madonna related 🙂 She has had a #1 hit (Music) in 2000 – and top ten hits: Don’t Tell Me, Hung Up, Four Minutes, and Give me all your Lovin’ – in this last decade. MANY # 1 dance songs too – extending her run on that chart even more and setting new records on both the hot 100 and dance charts. But I think as she’s gotten older (she’s turning 55 this week), radio has been reluctant to play her. Still, it’s pretty amazing she’s at all competitive with the younger artists still, and her last two tours are the biggest solo tours ever!

  5. Antje says:

    I had almost forgotten about this performance, because I usually skip “He lives in you” when listening to EDIAND. You are so right, a top notch performance. It brings back to my mind my favorite “DR project”, to have a DVD with her best TV- appearances. Just like the Supremes “Reflections”-DVD, but including less known songs as well. It could be very difficult due to copyright reasons, but I think it would be worth any efforts. So many have something like this on the market, but of course only few could hold up the candle to Diana at her best. It would have finely celebrated her 50th career anniversary.

    Paul, you said she looked fantastic. I do not completely agree. Her face appears quite different in comparison to other clips, before and after, especially since the 1990s. Watching, I often wondered, how does she “really” look like? So many clips, so many different – not looks, nor sometimes hair – but, yes, faces. Is it the lighting, the make-up, the angle, or whatever she might have had done? Do you know what I mean? I am not talking about aging. Sometimes I think it’s almost like different persons.

    • Paul says:

      Hey. Antje!! Personally, I think Diana looks great here — I really do. I do agree that she physically changed quite a bit during this period — but I’d say the changes really started in 2000. This was especially true of her appearance on the Barbara Walters Mother’s Day special and on VH1 Divas, too. Something looked “off” at times — there’s definitely been plenty of talk about her health issues (the “pausing time” she mentions in this interview) and, of course, her drinking. I’m sure those contributed to changes in her look in the late 90s/early 2000s.

      I will say that Diana has aged so much more gracefully than many of her peers. I recently saw an interview with another soul singer who was very popular in the 70s-90s, and the work she’d obviously had done to her face looked very unnatural, and had really changed her appearance. So glad that is not the case with Diana Ross.

      • Antje says:

        Do you have a link to the Mother’s Day Special? I’ve searched the internet, but in vain…
        Yes, I agree, she mostly looks quite natural and familiar, now more than around the 2000s. There was a shot from the Motown Musical Opening, it was so close to her Supremes’ time face. Though sometimes – I don’t know. Anyway, it is the voice that counts -still one of a kind!

    • T-Rox says:

      I agree with you Antje, Diana looked different in this Oprah’s episode, I think it has to do with muscle mass and tone, she was losting a bit of both in her “pausing time”, naturally, so her face didn’t look so angular as before.

      Having said that, she had several moments after that when she looked really fit and healthy, and much more angular than here. I think she was at a “off day” in terms of psychical balance that day on Oprah.

  6. Tony says:

    Wow! Really! I think she has aged beautifully ….doing only slight if any tweaks. This is obvious when we see her candid no make shots in the tabloids. She is for the most part …”untouched”. I think recently her teeth have maybe been corrected ….and I will say I don’t much like that thick toothed look she recently got. But as far as her face ….back then …I am sure she is all lights and make up ….Not ” work”.

    Just my observations!

  7. Antje says:

    Alright, I will start to list my favorite televised appearances. I hope you don’t mind, and hopefully this will not interfere with any upcoming reviews of yours, Paul!

    Absolutely no 1 for me is “Ain’t no mountain” on the Dick Clark Show 1978. One of the best soul-pop tunes ever, combined with a stunning, charismatic performance.
    No 2 is close, “The Boss”, an energetic delivery with superior vocals on “Standing room only” (1980) – what can I add to Paul’s wonderful review of this performance.
    One of my favorite songs, and a well thought out, sexy performance of “If you’re not gonna love me right” on Letterman 1995; no 3.
    “I’m still waiting”, Royal Albert Hall 1973, is no 4 for me. Loved it then, still love the song now. I am lucky having watched the show in Paris, though I am not sure resp. do not remember whether she performed the song there. Not easy for a mature woman or even mother to identify with the lyrics. Just compare this one to her tongue in cheek delivery on “An evening with…” from 1999.
    No ranking from now on: “Touch by touch”, American Music Awards 1985 – so sweet!
    Yes, “Love is all that matters” (this review on Oprah 1999) – it brings out her crystal clear and elegant, yet emotive voice so well after Brandy’s opening.
    On Oprah 2000 “Only love can conquer all”, because it is rhythmically so much tighter than the album version – and of course ending with an absolute generous gesture!
    “God bless the child” – introducing Billie Holiday into the Hall of Fame 2000; just sublime.
    Performing “Do you know” for the first time on “The Tonight Show” (1975). Such a nice delivery, made me feel at ease with the song, which is definetely not one of my loved DR’ ones.

    Wonder what your best DR-moments on TV are. Loooking forward to your choices and additions, guys!

    • Paul says:

      This is such a challenge! Love seeing your list, Antje. Many of these are moments I’ll be writing about soon! But I don’t mind at all discussing them early.

      Right now — I’d say a few of my top Diana television moments are…

      1) The opening of Standing Room Only: Diana Ross — when she comes out of the screen and onto the stage. A brilliantly calculated moment and still a thrill to watch today.
      2) “Ain’t No Mountain…” on theDiana! TV special. The moment at the end, where she practically begins head-banging to the beat, kills me every time.
      3) “I Will Survive” on “Late Show With David Letterman” — I love that she goes along with the crazy skit involving sunglasses, a bottle of Snapple, and a massage. She has a great sense of humor about the whole thing, and it’s delightful.
      4) “It’s My Turn” on “Oprah” in 2000 — she only sings a snippet of the song before becoming too emotional to continue, but what a snippet! It’s like a glimpse right into the singer’s soul. A real “wow” moment.
      5) “I’m Coming Out” at Central Park, Day 2 — There’s nothing like Diana sprinting backstage, tripping on the stairs, then emerging in front of the massive crowd with a rousing rendition of one of her best songs.

      …and there are SO MANY MORE!

  8. Tony says:

    I will need to take some time to review and assess options on this one. BUT ….I will say , I am 100% with you on the # 1 spot. It is for me “Ain’t no mountain” on the Dick Clark show without doubt and LOVE HANGOVER on the Midnight special as a close 2nd.

  9. Tony says:

    Oh God Paul….you are so right ….the entrance on Standing Room only ….still gives me goose bumps!!!!! I need to really think about all this!!!

  10. Pingback: Diana’s Duets (1981) | THE DIANA ROSS PROJECT

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