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The "What If?" Game: Whoopi Goldberg Edition

Dave Kotinsky/Getty Images
Dave Kotinsky/Getty Images

An unexpected, annoying, and occasionally entertaining biproduct of the untimely deaths of the Notorious B.I.G. and Tupac has been the "What if?" game hip-hop heads love to play. You've surely heard it before. It starts with a lament on how wack and soft today's artists are. And then someone says something like "If Biggie was still alive, Migos would be selling staples and chocolate milk in Home Depot parking lots" or "If Pac was still around, man, Obama wouldn't be on this post-racial shit. Cause Pac would have been president." And then everyone nods their heads, and continues taking sips of Olde English 800.


Of course, suggesting that one person's presence would have made hundreds of entertainers completely change their career paths is laughable. Also, the "What if?" people have absolutely no idea what would have happened to Pac and Biggie if they weren't killed. Maybe Pac would have discovered and dated Britney Spears. Maybe Biggie would have lost weight and tried out for American Ninja Warrior. Again, we have no idea. Because nothing ruins a legacy worse than a longer life.

That said, I also enjoy playing the "What if?" game. But from a different perspective. Instead of "What if this person who died stayed alive?" I prefer "What if this person who's still alive actually died?" How would that affect how we think about them? What effect would it have on their legacy?


For instance, right now, DMX is a punchline. A horror story Kanye shares when he tucks Big Sean in bed at night. But what if he died in 1998? I'll tell you what. He'd be remembered as one of the best rappers of all-time. Because no rapper — not 50, not Pac, not Eminem — ever had a better year than DMX's 1998. He released two multi-platinum albums in the same year. Ruled the clubs, the radio, the car stereo, the headphones, and the mixtapes. Oh, and he starred in Belly. Which sucked. But his screen presence and charisma was unmistakeable. It wouldn't have been a leap to expect him to continue to star in major motion pictures.

There'd be DMX documentaries. Terrible but successful albums composed of long-lost DMX freestyles reengineered and laid on Pharrell beats. Professional cornballs would have DMX tattoos. Since he rapped about death and Heaven and religion so much, there'd be multiple theories about how he faked his own death. "Ruff Ryders' Anthem" would be considered a classic, and listening to it today would make us feel nostalgic. But not good nostalgia. A sad nostalgia. Thugs would shed thug tears.

But while DMX's legacy would have received a huge boost from an early death, that boost pales in comparison to the difference between what we think of Whoopi Goldberg now, and what we would have thought if she died in 1992.

Today, Goldberg is best known as the batty woman who spews consistently problematic non sequiturs on a show watched by everyone's aunts; a fact John Oliver made light of last week, with a video compilation "Whoopi Goldberg Defends Ten Surprising Things." You can argue she's just being the devil's advocate. But after years of advocacy, you're no longer just an advocate. You're an ally.


But what if she passed in 1992? Or, I don't know, just became a recluse and completely withdrew from public life? Not only would we have never seen this Aunt Waiting For A Megabus At The Greyhound Station Even Though Megabuses Don't Stop There side of her, she'd be remembered as one of the best actresses of all-time. Perhaps the best.

This sounds ridiculous now, but consider her nine-year stretch from 1983 to 1992.


1. Created The Spook Show, a one-woman show composed of different character monologues, in 1983. Mike Nichols offered to take the show to Broadway. The show, retitled Whoopi Goldberg for its Broadway incarnation, ran from October 24, 1984 to March 10, 1985, for a total of 156 performances; the play was taped during this run and subsequently broadcast by HBO as Whoopi Goldberg: Direct from Broadway in 1985. She won a Grammy for this.

2. Starred in the Color Purple, and received an Oscar nomination for Best Actress


3. Starred in Jumpin Jack Flash and The Long Walk Home — two movies I remember watching on HBO on days I was home sick

4. Starred in Ghost, and won an Oscar for Best Supporting Actress — the first Black woman to win an Oscar in 50 years


5. Got a recurring role on "Star Trek: The Next Generation"

6. Starred in Sarafina!

7. Made Sister Act. Which only made like 900 million dollars

That's two Oscars nods. One win. A Grammy. Two iconic movies. Hundreds of millions in box office gross. And evidence she could do comedy, drama, sci-fi, and Ghost — which combined all three — without losing a beat. All in nine years. Do you know how many documentaries, movies, biopics, books, thinkpieces, blog posts, monuments, high school curriculums, and college course syllabi would be devoted to Whoopi today if 1992 was the last we saw of her? Her name would be on more shit than Martha Stewart's.


But, when thinking about her today, none of her legitimately amazing accomplishments register. Her erratic behavior and batshit words have made us collectively suppress the fact that she was the shit. And not just the regular shit. But the "this aint never happened before" shit. The historic shit. It's like your neighbor making the best Thanksgiving meal you've ever had. And then learning, a day later, that great turkey was actually your neighbor's dog.

Of course, the "What if? game is just a game. We can only deal with our actual reality, not the reality that might have happened. And, of course, I'm sure Whoopi is very happy she's continued past 1992. As am I. The world is ultimately better with her in it. (And, earlier today, she did reverse her stance on Cosby.)


Her legacy, though? Well…at least she aint DMX.

Damon Young is the editor-in-chief of VSB, a contributing opinion writer for The New York Times, and the author of What Doesn't Kill You Makes You Blacker (Ecco/HarperCollins)

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If I am not mistaken she is the first African American woman to ever hold a Oscar, a Grammy, a Tony and an Emmy. She was the first to host the Academy Awards. She broke records in comedy and as a producer (dating all the way back to Hollywood Squares). She made a path where there was none, and spit in the face of respectability politics and beauty standards. To have Whoopi be as famous as she was at a time when NO brown faces that looked like hers was a revelation. I wanted to be her when I was a kid. She was my inspiration. And I mourn. I am devastated. It's not like we have a whole bunch of us in media that are as full of accolades despite not being the preferred "type". It's hard, man.