The Brief Acting Career of Diana Ross

Diana Ross. Ms. Ross. The Boss. The preeminent diva of my lifetime. The pop icon I think of when I picture a woman who embodies the word “diva” in all its majesty and splendor.

Like many a millennial, I grew up with the Supremes and her solo work as the background noise of my childhood at family functions. As I grew older, I learned to appreciate and adore not just the Supremes but so much of her solo material. Seriously, between 2001’s Anthology (group) and The Motown Anthology (solo), Diana Ross’ musical legacy is enough to place her in the upper echelon of pop goddesses.

But there was also a brief time when she branched out into acting. And she was damn good at it, too. In-between releasing chart dominating albums, Emmy winning TV specials, and collecting a Special Tony Award, she made a handful of films in the 70s that demonstrated a unique glamour and skill that has been sorely missed and lacking from cinema ever since. (Even if the quality of the films were uhm, varied.)

I will be seeing her in concert for the first time in late February, a bucket list item that I am thrilled about finally being checked off. But it also got me thinking about her brief stint as singer-turned-actress and how I wanted to either revisit those films or watch them for the first time. So, here we are exploring the brief, wondrous acting career of Diana Ross.

I will be discussing just her film and TV movie roles. Nothing about any of her numerous music/variety specials, although those are worth a watch if you ever want to see a perfection visual description of the unique glamour and oddity of the 1970s pop scene. That leaves us with just five works spread out over a 27-year period, which is a minimal amount but she accomplished quite a bit in that brief body of work.

Lady Sings the Blues, Billie Holiday’s 1956 dubiously factual autobiography, started development in 1959 with Ava Gardner and Columbia Pictures involved. Thankfully, and mercifully, this version withered on the vine. Production picked up again in the early 60s with Dorothy Dandridge attached to the central role. By the time serious development on the film started, Dandridge had died tragically young (42, not much younger than Holiday’s tragically young 44), and the film languished in development hell. Motown Productions eventually came into the picture in the early 70s.

The fact that Motown was involved in the final product is important to the eventual casting of Ross as Holiday. From my brief research into the production, names such as Diana Sands, Abbey Lincoln, Diahann Carroll, Cicely Tyson, and Lola Falana were brought up at certain points and during various false starts. Sidney J. Furie may have the director credit, but the final film is all Motown gloss with the fingerprints of Barry Gordy nearly everywhere, including the often guffaw inducing montages or juxtapositions.

But this was how Diana Ross secured the role of Billie Holiday. None of this is mentioned to denigrate the incredible achievement of Ross’ debut performance, but merely to provide context and how the final film came into being. For better and worse, Lady Sings the Blues is loosely based on Holiday’s already loosely true autobiography and works best merely as a vehicle for Ross’ movie star coming out. Although, I do wonder who decided that Ross should play the part from 14 through 33 because watching Ross trying to project a girlishness and juvenile body language is an awkward sight.

Things markedly improve as Holiday ages into her early 20s and start singing in clubs. It is here that Ross’ work takes stronger shape and function. As Holiday endures one indignity after another, starts drinking and shooting up, Ross’ performance demonstrates an intelligence and range that belies that this is her first try at the craft. But plenty of great pop stars have been able to make the jump because performing lyrics and crafting a stage persona is similar to crafting a character and finding the emotion in a line reading.

Much has been made of her guttural howls that open the film in a flashforward to an arrest, but I was disturbed and haunted by the animalistic fury she brought to a scene where she begs and demands to be left alone in the bathroom to shoot-up opposite Billy Dee Williams. The vision of Diana Ross as heavily made-up and immaculately dressed pop star is burst in an instant as she claws and swings a razor. Then we watch her again as the heroin takes hold and the inner life/spirit of this woman recedes into the ether. More well-respected professional actresses have struggled to achieve the believability and hunger she conveys here.

Just as great is a smaller scale scene where she asks her white bandmate for a hit after a particularly depressing professional setback at a radio show. She tries to keep stable while anxiously moving her hands and smiling through the pain. These small little notes provide a glimpse of Ross’ gifts as an actress. It is just a shame that they are not in service of a better film.

But there seems to be something cursed about these big, glossy prestige films about Holiday. 2021’s The United States vs. Billie Holiday has similar tone and structure problems: a heavy dose of fictionalization, a tremendous pop star debut acting performance, and a flagrant disregard for the complexities of the subject’s life. In Lady Sings the Blues, Holiday’s romantic life is unusually stable with Billy Dee Williams’ Louis McKay. In truth, McKay was a low-rent crook, but here he is the dashing, stable, impossibly handsome knight waiting and willing to save Holiday from her slow-moving self-immolation.

Even worse is how Furie sometimes juxtaposes an incident with a song. The most offensive of these is Holiday stumbling upon the aftermath of a lynching only to smash cut to her, in full regalia, singing “Strange Fruit.” This sequence feels like an affront to Holiday’s art, as does the ending Carnegie Hall concert where Ross’ “God Bless the Child” is superimposed with headlines that barrel us towards her tragic, premature death. We then cut to Ross’ arms raised in triumph as the film ends. The film routinely has a questionable level of taste.

The film often feels too long, too unwieldy, too obvious and familiar, but it is routinely saved by Ross’ work. While her singing is nowhere near the artistry of Holiday’s singing, Ross manages to find the intonations and phrasing of Holiday without repeating the sound. Then there is the general sense of Ross’ acting which is vulnerable and raw, glamorous and lovely, unafraid and bruised. While the film often rings false, everything Ross does rings true. It is an act of movie star salvaging to the core, and this was her first time.

Ross got Oscar nominated, and made history not only for being one of the few Black performers nominated for their debut film performances, but for being one of two Black actresses nominated in the same year. Cicely Tyson in Sounder was the other, and both lost to Liza Minnelli in Cabaret. This feat would not repeat until the 2021 ceremony where Andra Day’s film debut as Billie Holiday got her Oscar nominated alongside Viola Davis’ Ma Rainey. Once again, both lost.

1975’s Mahogany was at one point intended as a Liza Minnelli vehicle, and it seems nearly impossible to picture her as the starry-eyed fashion plate yearning to make it big as a designer. A majority of Minnelli’s charm was less in being a fashionista than her being a thoroughbred entertainer in the Broadway tradition. She was a grand dame of the stage, a Broadway baby in the long tradition of Gwen Verdon, Ethel Merman, and eventual costar Chita Rivera. Diana Ross, in contrast, always had glamour as part of her persona.

Part of the reason the Supremes took off was because of the outsized glamour they brought to their performances: big false eyelashes, flowing gowns, sparkle, and elegant hairdos while swaying in high heels. Ross especially caught the eye because of the sophistication she projected in their televised performances. This continued on as she went solo and wore sleeker, sexier bodysuits and oversized coats that were quickly tossed off for maximum “wow” factor. She makes sense as the lead of an old-fashioned woman’s picture like Mahogany.

It’s just a shame about the muddled script and direction. But unlike Lady Sings the Blues, this is entertaining trash. Weird and wild as it is, Mahogany delivers on the promise of Ross and Billy Dee Williams romancing each other, Ross serving looks, and Anthony Perkins being a weirdo. It is not good exactly, but it scratches a similar itch to the working girl-makes-good/old-fashioned makeover films of Joan Crawford, Ginger Rogers, and Bette Davis throughout the 30s and 40s.

As Roger Ebert mused: “The movie's got rich costumes, romantic music, decadent playboys, socially redeeming values and a fable of rags to riches. Why should it have to make sense?”

Good question, because so much of it does not. Tracy (Ross) works her minimum wage job, goes to art school at night, and dreams of the fashion world and becoming a top designer. She meets Brian (Williams), an activist and political candidate, and sparks fly from the beginning. Ross and Williams really did have great chemistry together as they naturally balanced each other out. Ross’ delicacy and flightiness is counteracted by Williams’ smoothness and hunky posture. If only for a brief time in the 1970s, they represented a mainstream Black movie star glamour within the commercial film industry.

Then Anthony Perkins enters as a famous fashion photographer with his sights on Ross’ Tracy, who he christens with the moniker Mahogany. Perkins’ role is a villainous queer-coded thing that brings an uncomfortable energy to the movie that it never quite knows what to do with. His obsession with Mahogany involves a failed sexual encounter (he can’t get it up) and a homoerotic tussle with Williams (where a gun gets put in his mouth while wrestling). After he intentionally crashes his car, a patently ludicrous sequence, with Tracy/Mahogany in the car, he exits the film and it quickly barrels towards a happy (?) ending where the lovers are reunited.

The whole thing feels like Jacqueline Susann novel without the commitment to the bit. The behind-the-scenes turmoil saw original director Tony Richardson fired by producer Berry Gordy, who eventually took over as director. Given his romantic and financial interests in Ross at this point, his directorial eye is merely one that passively watches as her ego runs amuck in the frame. Modeling montages and costume changes pileup along with loving closeups of Ross’ face that emphasize her large eyes.  

In the end, I am not sure what to make of Mahogany or what it is trying to say. If it has anything to say at all, even. But I had fun with it in a “so bad it’s good” way. Ross gets to be funny, strike a pose, wear killer outfits, and lean into her innate megawatt star power. Sometimes, that’s enough.

A musical seems like an absolutely odd choice for a director like Sidney Lumet, a director that was preoccupied with grit and realism during this period. But that eye towards grit and realism made for a unique collaboration with 1978’s The Wiz, which creates an imagined, fanciful New York, a New York in which graffiti comes alive and dances, and the yellow brick road extends from Harlem to Manhattan and beyond. And the film offers Lumet a chance to explore his favorite subject, New York City, in a new prism.

It’s a mystery to me why this film has such a terrible wide reputation, consider me part of the cult following. It is not perfect, but it is an excuse to watch Ross, Michael Jackson, Lena Horne, Mabel King, and numerous other great talents sing, dance, and deliver comedic bits. If that is not enough entertainment value for you, what more do you need? The Wiz also has numerous sequences that are full of clever bits and details, or imaginative images, or memorable songs, the basic tenets of what a musical need to succeed, and it does.

Admittedly, Diana Ross is still too old for the role of Dorothy has written here. No longer a young schoolgirl making the transition into adulthood, but a teacher in her early twenties struggling in an extended adolescence. Ross is clearly in her thirties, but she does possess vulnerability as an actress, a quacking need, and wide-eyed sweetness that works for the role. It is easy to forget just how talented an actor she really is given just how miscast she is in the lead.

Much like the beloved classic, The Wiz finds Dorothy swept away to Oz, it is hinted that Glinda the Good Witch summoned her there, and on a journey of rediscovering her personhood and inner strength. Along the way, she meets up with the Scarecrow (Michael Jackson), the Tin Man (Nipsey Russell), and the Cowardly Lion (Ted Ross, repeating his role from the Broadway triumph). With the help of her friends, she must battle the evil witch, Evilene (Mabel King, also reprising her Broadway role), discover the secret of the Wiz (Richard Pryor), and get lessons from two good witches, Miss One (Thelma Carpenter) and the beatific Glinda (Lena Horne).

Perhaps The Wiz suffers from comparison to the classic 1939 film? No film should have to eternally live in the shadow of another, especially one with so radically different an approach and tone to the material. The Wizard of Oz created a world of pure fantasy and whimsy, a dreamscape for its heroine to ease into adulthood. The Wiz has a heroine who is afraid to leave home and strike out on her own, and her Oz is no less magical, but it is a fantastical variation of her real-world location. I think it works on its own terms, even if it does take a little too long to get where it is going.

Once Dorothy lands in this topsy-turvy Munchkinland, here re-imagined as an inner-city playground with black-light graffiti people and a numbers running witch named Miss One, The Wiz is firing on all cylinders and propels forward towards its narrative conclusion. This is roughly thirty minutes into the film. It’s not that what has preceded it was not engaging, but the tone was too sleepy.

After this awkward start, we are treated to numerous memorable performances and moments. No moment hits with quite the same impact as “Everybody Rejoice/A Brand New Day.” Following immediately after the death of Evilene, again not a spoiler as this follows the basic story structure of The Wizard of Oz, this scene finds her various slaves removing the vestiges of her oppression and dancing with great abandon and joy, a joy that becomes infectious. The scene swirls around as chorus of bodies leap about the room, remaking themselves into clean slates and ready to return to their normal lives. It is the kind of magical moment that only a musical could provide.

Other highlights include Jackson’s “You Can’t Win, You Can’t Break Even,” a song the Scarecrow is forced to sing for the crows over and over. Jackson is pinned in one place, but his love of movement is clear. His ability as a dancer allows him to create a series of awkward, pained movements as the Scarecrow does not have complete control over his body. Jackson and Ross jubilantly skipping on the Yellow Brick Road and singing “Ease on Down the Road,” the musical’s most well-known song, is another highlight. And, of course, Lena Horne’s reprise of “Believe in Yourself” is a knockout moment. Horne’s Glinda is a glowing presence, and only an icon of her stature would have given the part and the song the gravitas it required. Ross’ elated crying is the only appropriate reaction to Lena Horne singing directly to you, telling you to believe in yourself, and offering encouragement and support.

The elaborate production and costume design refashions and recreates various landmarks and parts of New York City life into fantastical elements. The film also plays with color in various scenes to grand effect. The introduction of the Emerald City finds the denizens and large crystals decorating the area changing colors in the blink of an eye. This Emerald City owes more to Studio 54 than the metallic, massive one Judy Garland wandered into. It’s no surprise to me that these three elements were Oscar nominated, they were pretty stellar.

It is a little bloated, a little messy, but you’ve got a killer cast, a series of images that are always interesting, and a very pleasant score. It is an endearing cult classic, and, dammit, I think it deserves to be better loved and embraced. Perhaps a reevaluation will be in order sometime soon.

After The Wiz sent her acting career into hiatus, let’s call it that and move on, there were numerous rumors that she would return to the big screen in various projects. There was the time when Ryan O’Neal almost got an earlier version of The Bodyguard off the ground, allegedly Ross objected over potential nude scenes. The Main Event had her name tossed about, but her acrimonious split with O’Neal sometime between the 1978 development of The Bodyguard and 1979’s The Main Event shot down that idea. Then there were the rumors of a part in The Witches of Eastwick, but that trio of roles had seemingly every actress between 25 and 40 mentioned as a potential candidate so who knows how serious that idea was.

Frankly, the most intriguing shelved project was the biopic about Valaida Snow and the controversy around her claims of surviving a concentration camp. That sounds like the kind of juicy leading part that should have come immediately in the aftermath of her Oscar nomination, or after the box office success of Mahogany. Whatever became of it beyond its initial development announcement is unknown.

But there are two famous what if’s/almost was films: The Color Purple and a Josephine Baker film based off the 1981 biography, Naked at the Feast. Steven Spielberg was circling singers for the part of Shug Avery in The Color Purple. Most famously, Ross, Chaka Khan, Patti LaBelle, and Tina Turner, each of whom turned it down for various reasons. Ross’ megawatt glamour would have worked but could she have brought the grit and allowed herself to play the character’s bisexuality? Unknown but probably not given the removal of Holiday’s queerness in Lady Sings the Blues. Of all the casting call names bandied about, Sheryl Lee Ralph would have been something to see in the part.

Would she have been stellar in Naked at the Feast? Who knows! Allegedly, there was a script, a director, and a rough shooting schedule and financing being worked out with TNT or TBS before the plug was pulled. Come 1991, HBO released The Josephine Baker Story starring Lynn Whitfield in her Emmy winning performance. Ross’ crack at the project was shelved, but perhaps she felt a certain kinship with Baker’s long and rough road to showbiz glory. Ross and Baker both had to project and maintain a perfect, untouchable image, function as a “credit” to their race in their home country during a time when opportunities were scarce and limited. Maybe, much like she did for Lady Day, Ross could have dug deep into her own psyche and pulled out something as truthful.

The closest we will ever get to seeing Ross in action as Baker is during a brief, and bizarre, interlude during 1977’s An Evening with Diana Ross. This is a filmed version of her Broadway stage show that won her a Special Tony Award. During a tribute to the “working girls” that came before her, Ross hallucinates Baker, Bessie Smith, and Ethel Waters appearing in the audience and talking with her. Ross plays all three, in various levels of prosthetics courtesy of Stan Winston and skin tones, and makes the argument that she exists along a continuum with them, essentially standing on their shoulders while widening what is possible for the next generation to achieve.

Two things immediately come to mind while watching this segment: Ross really was quite the little actress at this time as her body language, vocal mannerisms, and entire persona shift and glide across four distinct characterizations, and it is also a little weird/uncomfortable seeing her darkened to play Waters and Smith. Questions and discussions about lighter skinned actresses either playing darker skin parts or getting made up for them are still happening. Zoe Saldana in the Nina Simone biopic springs to mind as one example. Zazie Beetz playing Stagecoach Mary in The Harder They Fall as another.

Her return to acting, sixteen years after her last role, was in 1994’s Out of Darkness. This made-for-television drama is less the story of a woman overcoming illness than a disturbing portrait of what it is like living with paranoid schizophrenia. The disease not only complicates the lead character’s life, but we watch as her condition derails her family’s life and relationships as well. The saccharine, hopeful “disease-of-the-week” fare from the time period it is not.

From the jump, Ross is nearly unrecognizable so buried in the sweaty paranoia and emotional intensity of this woman that the pop icon seems a figure of the distant past. We see the dramatic work that might have been. The roles not taken, or perhaps the roles not offered because however poor the representation and material for Black actresses is now, it was incalculably worse and more limited between the 1970s and 90s.

What really impresses with Ross’ committed work is not just the physicality but the ways in which her face and eyes change. You can see the emotional/mental storm rolling through and settling in. The light and life disappear as a hard edged and defensive nature takes over. At other times, a crazed mania flashes across her face, all bugging eyes and closed fists flailing about. Combined with the physicality, including a walk she achieved by placing an orange between her thighs and keeping it in place without the aid of her hands, we are reminded of what a talented actress she can be with the right material.

But all Out of Darkness winds up being is a star vehicle for Ross’ immaculate performance. The rest of the characters get short shrift – a longsuffering mother, a sister who feels neglected, other patients, and a supportive doctor with an experimental cure all appear but rarely evolve past these thinly drawn archetypes. The very nature of pre-Peak TV often leaves these things feeling rushed or partially formed. The midsection of her treatment feels particularly glossed over as she goes from debilitating illness to experimental trial to functional in the blink of an eye. The midpoint of her journey seems to have not interested the creative team as much as her in freefall and tentative rebuilding did.

But credit must go to the filmmakers for ending it with an ellipsis instead of a period. After enduring the whole traumatic ordeal and seemingly getting her life back on track, Ross’ character watches a homeless woman mumbling to herself and the film lingers. Is this a vision of things to come or a vision of things that she has managed to avoid? We will never know, but you can draw your own conclusions. 

Five years later and Ross would return to acting with 1999’s Double Platinum, another made-for-TV movie. This time she plays absentee mother to Brandy, at the height of her crossover fame between Cinderella, Moesha, and her second album, Never Say Never. If you were expecting a generational diva-off, a battling of horns between established grand dame and hungry upstart, well, an R&B retrofitted All About Eve this is not.

Double Platinum opens in 1981 where Ross’ would-be chanteuse is struggling in an unhappy marriage and a music career that is going nowhere slowly. She is approached by someone who can promise her pop stardom, but she has to leave Atlanta for New York City. She abandons her stifling husband and infant child and we jump forward in time to (then) present-day where Ross’ pop iconography provides quick shorthand for the success and career she has managed to achieve.

It is in the turbulent reunion with her daughter, also an aspiring singer, that a majority of the film’s narrative heft and drama take place. But this was a TV movie made in the pre-Peak TV age, so the quick shooting schedule and thin script relies heavily upon the outside knowledge of Ross and Brandy to paper over these elements. It also helps that a bevy of Broadway stars (Brian Stokes Mitchell, Harvey Fierstein, Christine Ebersole, Roger Rees) are brought in to provide color to underwritten supporting parts. If made now, this would probably be a few episodes too long limited series.

Ross is hit-and-miss here. At times, she looks unsteady about what emotional register to hit in a given scene, or rests on her image to do the work for her. But there is a tender, awkward, honest scene at the end where she stutters and stammers and admits that if she had to make the choice over again, she would not change a thing. If Ross is a touch rusty as an actress, she still eclipses Brandy, who gives a listless and surface only performance.  

All told, Double Platinum is a generic TV movie from its era. Nothing more and nothing less, but one with a better than average soundtrack given the preponderance of songs from both stars’ albums. It is not an embarrassment of a final role, if it even is a final role as rumors have continually persisted that Tyler Perry wants her for a movie. Who knows if it will happen, but at 79, there is still time for one last glimpse of Diana Ross, actress.

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