‘Jackie’s Back’: The Best Mockumentary You’ve Never Seen Turns 25

Do you know what you’re doing for Jackie Washington Day next month? You know, July 15, Jackie Washington Day! It’s the annual holiday that celebrates legendary music superstar Jackie Washington, singer of such unforgettable hits as “Wednesday Night Fever,” “Love Goddess,” and “Take Your Jeri Curl and Go.”

On second thought: Maybe it’s better if you don’t have any plans. After all, people are known to randomly drop dead on Jackie Washington Day.

At least that’s the popular consensus among the procession of talking heads in Jackie’s Back, the brilliant yet under-the-radar 1999 mockumentary starring Jenifer Lewis as the titular diva, Jackie Washington. Directed by the great Robert Townsend, Jackie’s Back was originally released as a TV movie on Lifetime in June of 1999. That means that the film is celebrating its 25th anniversary this year, and given that the film is now also streaming entirely for free (with a few ads) on Tubi, there has never been a better time to heap praise on this little-seen gem.

One-quarter of a century on, Jackie’s Back has only become more searing and astute. Its script, penned by Dee LaDuke and Mark Alton Brown, is a deluge of endlessly witty running character gags, celebrity cameos, and incisive commentary on Black pop culture. It’s closest in the vein to Christopher Guest’s For Your Consideration—where three washed-up actors try to make an Oscar-worthy comeback—but more punchy and fraught than any of Guest’s classic mockumentaries. Jackie’s Back is a plainly ridiculous romp, led by a typically fearless Jenifer Lewis, whose performance is an all-around comedic triumph that will remain permanently lodged in your head from the moment you first meet the diva, Jackie Washington.

Jackie Washington’s life is so storied and chaotic that we need our hands held by a professional to even begin wading into her turmoil. Our intrepid guide to this topsy-turvy pop prima donna is Edward Whatsett St. John (an always-game Tim Curry), who kicks off the in-film documentary, Jackie’s Back: Portrait of a Diva, with a question. “Who is Jackie Washington precisely?” Edward asks the viewer. “Former child star, pop diva, down-and-out boozing has-been. Those are the accepted preconceived notions.” From there, we are thrust into the next 90 minutes of zeitgeisty debauchery, and introduced to a few of the famous names interviewed for the film to comment on their industry colleague.

The credits of Jackie’s Back are a who’s who of the late ’90s A-List. There’s Dolly Parton (“Jackie Washington…who exactly is Jackie Washington?”), Rosie O’Donnell (“I love Jackie more than Snickers!”), and Diahann Carroll (“Is she making another comeback? This child makes more comebacks than anybody I have ever known in my life. Alright, if she wants to make another comeback, that’s fine!”), among countless others. Even Whoopi Goldberg appears as Jackie’s sister, Ethyl Washington, who tells us all about the strange happenings in their hometown of Kinloch, Missouri, every July 15, which the mayor has dubbed Jackie’s holiday.

We quickly sense that Jackie is not as universally revered in the industry as her peers Diana Ross and Gladys Knight. She’s made as many friends as she has enemies. Kathy Griffin is a big supporter, telling the camera: “Jackie, with no Botox and at all, looks just calm, serene, and beautiful, and she just is Jackie. If that isn’t a diva, then Celine, get the hell off the stage.” Penny Marshall, though? Not a big fan. “Trying to come back from nowhere is a little hard,” Marshall says.

But Jackie is, nevertheless, determined to show the world that she still has it. Jackie’s Back cleverly mines our collective cultural obsession with the downfall of superstars, which was even more rampant in the years just before the tech boom made tabloid culture the apex of social fascination. In that respect, the film feels gleefully analog. It’s a convincing mockumentary because of the absence of social media; we can more easily believe the exorbitant, inane antics that Jackie got into throughout her career because we see them making newspaper headlines and affecting her album sales. It just wouldn’t be the same to see someone’s Instagram followers tick down, or watch their Spotify streams dry up. Making something like Jackie’s Back today wouldn’t necessarily be impossible, just a hell of a lot harder.

Jackie has had such a long and arduous career because she shot to fame so quickly. Her hit single, “Yield (Before You Hit Me With Your Love),” is a preposterous, The Supremes-esque number featuring traffic signs and driving metaphors. (“Don’t tailgate me, mister, because I’ve got a heavy load!”) After that, Jackie broke out on her own, and was revered as one of the great child-singing stars, alongside Michael Jackson and Stevie Wonder. But as Soul Train host Don Cornelius puts it, “Jackie had the most raw talent.” Jackie’s career saw a few hits, a few flops, an Oscar performance, and even a live album: Tore Up from the Floor Up: Live from Compton.

During her singing career, Jackie had a few misses. There was a philandering manager, some incidents of public drunkenness, an unfortunate photo of her cozying up to President Nixon, a blaxploitation film called Coco’s Revenge that was so bad it managed to end the entire subgenre, and some tricky litigation after her 2-in-1 facial toner and hair relaxer, Essence of Jackie, was recalled for giving customers severe chemical burns. But all of that is behind her as Jackie prepares for her comeback concert at the Hollywood Theater. She arrives in a limo she hired just for the occasion, flanked by her daughter Antandra (T.V. Blake), who functions as Jackie’s wrangler and assistant.

As we watch Jackie get ready for her big night—and dodge invoices from a deaf pianist, the Russian theater manager, some scrawny twinks hired to be her backup dancers, and other palms waiting to be greased—we get the sense that this is her defining moment. This concert could make or break her career, and all her fans will be watching. Watching Jackie Washington on this night will be like being at Woodstock or seeing David Byrne in Stop Making Sense: the kind of once-in-a-lifetime experience that you’ll tell your kids about. But Jackie is just unsure about this as her adoring public is, though she won’t let anyone see her sweat. “Mama needs her cough medicine, and make it a double, Antandra,” Jackie says to her daughter with a wink.

Lewis is so mind-blowingly astonishing as she flits about as Jackie that it’s hard to believe Jackie’s Back isn’t universally heralded as one of the best mockumentaries of all time based on her performance alone. Not only does she deliver expectedly excellent vocals in all of Jackie’s absurd original songs, but her adlibs in her dialogue and physicality are unmatched. She commands the frame in one moment, stomping through a room with her shoulders back. The next scene, she’ll be hunched over and wincing in pain, Jackie’s massive breasts taking a toll on her posture. There isn’t one second of the film where Lewis isn’t on, and it’s a hoot just to watch how utterly committed she is to getting this right.

Not only does Lewis understand the movie’s comedy, but she’s got firsthand knowledge of its industry-skewering commentary, too. When asked a question about her career tanking because of her own boozing, Jackie brilliantly flips the script. “Let me tell you how Hollywood works,” Jackie says. “Yeah, Hollywood!” Lewis turns her head to break the fourth wall and look directly into the camera, as if she’s sticking it to the music industry suits and exposing them. Instead of taking ownership for her own mistakes, Jackie attributes her career snags to Hollywood only letting one Black woman slide through their gates every few years. Although Jackie is discussing a genuine reality of the entertainment industry, her co-opting it to excuse her personal blunders is exactly what a diva would do.

The industry might look a bit different 25 years later, but not much has changed. It’s still difficult to make a career comeback once the schadenfreude-hungry public has decided that your time in the limelight is done, technology just makes it easier to maintain some modest presence. But it wouldn’t be nearly as fun to watch Jackie Washington attempt to navigate the unregulated state of entertainment today (although I would love to watch Jackie interact with a TikToker trying to steal her spotlight).

The shocking level of cameos by the ultra-famous alone is enough for Jackie’s Back to feel dated. It’s sad to say that I can’t imagine a modern reality where anyone as big as Liza Minnelli and Bette Midler would be down to jump into a project like this, as they were then. Now that anyone can achieve some level of fame—and everyone has the ability to publicly criticize them—many celebrities have lost their sense of humor. Stars aren’t as willing to make fun of themselves, whereas every single famous face that appears in Jackie’s Back is in on the joke.

No one in this mockumentary has signed onto it to promote their work, only to lampoon it. Their lack of preciousness over their image is what makes Townsend’s film so damn unique. In 1999, Dolly Parton was suing Jackie Washington over a relaxer that nearly killed Dolly’s poodle. In 2024, Bradley Cooper is appearing on Abbott Elementary to do the Rocket the Raccoon voice. One was joyous self-deprecation, the other was a painful dreck designed to be a post-Oscars victory lap, but they both told viewers all they needed to know about each celebrity’s motivations.

Maybe the era of mockumentaries this sharp is bygone, or maybe HBO and Lisa Kudrow will finally pull the trigger on that long-rumored third season of The Comeback soon and prove me wrong. But unless that happens, Jackie’s Back will continue to stand proudly, as undaunted as Jackie, outside of this subgenre's more popular films. And though the film has already become a cult classic among a small swath of gay men and smart women, it’s okay if you were a little late to the party. Such is the case with plenty of legendary divas! And, as Diahann Carroll says in the film, “Diva is a word that some gay man made up.” Like all the best divas, Jackie is both real and unreal, and that’s what makes her so damn remarkable.