And the Skippy Goes To!: The Root's Inaugural The Blackest Awards Winners

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Illustration: Jim Cooke (G/O Media)

What’s up, Black America! Now that the Oscars have come and gone and awards were given to winners and what not and henceforth, it’s time to redirect that energy back into what matters most: celebrating Blackness in all of its Black Excellence Achievement. And that is exactly what we’re doing here with the Skippies. You see, at The Root, we believe the children are our future and that if we teach them well and let them lead the way, that if we show them all of the beauty they possess inside and give them a sense of pride...you already know where this is going. Also, Rest In Paradise, Whitney Houston. It’s been eight years.

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To The Skippies!! Last week, we brought you the nominees in nine categories for The Blackest Awards in celebration of often unrecognized blackness. At cinematic awards shows, those who have put in work in our community rarely get the opportunity to bask in their cultural significance in a major way. At The Root, we hope to change this; we don’t just actively participate in the culture, we celebrate it. So without further ado, and after taking into account the thousands (!!!!) of votes cast in our inaugural The Blackest Awards aka The Skippies, in honor of The Root co-founder, Dr. Henry Louis “Skip” Gates, Jr., we’d like to announce the winners. Each winner will receive a virtual trophy that represents a form of blackness familiar to me and you, your momma and your cousin, too.

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Additionally, while you were able to vote for nine awards, we are also instituting an annual Lifetime Achievement Award (chosen by The Root’s awards committee), given to the individual (or individuals) whose career has been devoted to black television and/or film and whose works have helped advance the culture and art form. We will also be naming the award after our inaugural recipient of the Lifetime Achievement Award.

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Thank you for voting and participating and tune in for next year’s awards as it gets bigger, better and blacker!

THE ROOT PRESENTS THE BLACKEST AWARDS IN HONOR OF DR. HENRY LOUIS “SKIP” GATES, JR., AKA “THE SKIPPIES”

The Lifetime Achievement Award (to be now known as The Clifton Powell Lifetime Achievement Award)

Winner: Clifton Powell

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Photo: Leon Bennett (Getty Images for BET)
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Clifton Powell is 2020’s Recipient of The Skippie for Lifetime Achievement Award because of his near omnipresence in black cinema for the past 30 years. From roles in classics like 1993’s Menace II Society, 1995’s Dead Presidents, and 2004’s Ray to memorable roles like Pinky in Friday After Next or internally known black classics like Who Made the Potatoe Salad? and The Gospel, Clifton Powell has acted in both television and cinema since the 1980s and shown up in so many films that are central to discussing black cinema. The Root decided that for his outstanding work and vast catalog dedicated to showcasing various forms of the black experience—and because of our desire to give our legends their flowers while they can still smell them, Clifton Powell is our 2020 inaugural recipient of the Lifetime Achievement Award, henceforth named The Clifton Powell Lifetime Achievement Award.



Ester Rolle Black Mother Award

Winner: Phylicia Rashad

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Photo: Dia Dipasupil (Getty Images for BET)
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Phylicia Rashad, who entered most of our lives as one of the GOAT moms, Claire Huxtable on The Cosby Show, has continued to play roles on TV, film, and Broadway that exemplify exactly why her win in this category comes as no surprise. Claire Huxtable is a mother to us all, and Phylicia Rashad made it all feel real. “Big fun” has never been the same since.



James Avery Black Father Award

Winner: John Witherspoon

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Photo: Michael Buckner (Getty Images)
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John Witherspoon, who passed away in October 2019, is famously known for several roles as a parent with a sharp tongue, an allergy to bullshit and wisdomific gems like, “don’t be pussy-whipped, you got to reverse that. WHIP THAT PUSSY!” from 1992's Boomerang. Along with his role as a father in movies like Boomerang and Friday, he also served as the voice of Granddad in Cartoon Network’s animated adaptation of Aaron McGruder’s The Boondocks, serving as one of the more popular characters on the show.



Best Black Person Playing Another Black Person in a Biopic

Winner: Denzel Washington as Malcolm X in Malcolm X (1992)

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Photo: Kevin Winter (Getty Images for WarnerMedia)
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Denzel Washington is one of the few people in America who goes by one name. His acting is unparalleled; his ability to make every role he takes into an experience is how he got to one-name status. So it comes as no surprise that he wins this award for his portrayal of one of the most iconic black people to ever have lived, Malcolm X, in the movie Malcolm X. The movie and his performance are so culturally significant that they breathed new life into the icon’s legacy and reinvigorated the “by any means necessary” ideology, illuminating the life of a pioneer of unapologetic blackness.



Love Jones Award for Best Black Movie Soundtrack

Winner: Purple Rain (1984)

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Photo: Warner Bros.
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Easily one of the best albums AND soundtracks of all time, it’s no surprise that Prince’s magnum opus, Purple Rain, takes the win here. The album is chock-full of hits like, “When Doves Cry,” “Purple Rain,” “Let’s Go Crazy,” “Darling Nikki,” “The Beautiful Ones,” and “I Would Die 4 U.” Prince, who passed away in 2016, is one of the world’s greatest artists and Purple Rain was a showcase for just how brilliant he was.



The My Office Hours Are From 9-5 Award for Most Iconic Scene In A Movie or Television Show

Winner: Kunte Kinte refusing to be called Toby in Roots (1977)

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Screenshot: Roots (1977 (YouTube)
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I wasn’t even alive when this miniseries, Roots, aired in 1977, but even if I’d never seen it, scenes such as this one have become so iconic in the black community that references to it have turned up in other shows, like The Fresh Prince of Bel-Air. My guess is there are very few black American children named Toby, largely because of this show and scene.



The “Until You Do Right By Me…” Award for Most Iconic Statement Uttered in a Movie or Television Show

Winner: “All my life I had to fight…” - The Color Purple (1985)

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Screenshot: The Color Purple (1985 (YouTube)
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I mean, is there anybody in African America who HASN’T uttered this phrase to somebody at some point in life? I say it to my own children three or four times a day. I said it at work in the middle of a meeting once and the only other black person in the room shot me a look of both disappointment and respect. All my life, I had to fight, fam. Super facts. Oprah did that.



You Did That! Content Creator of the Year Award

Winner: Ava DuVernay

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Photo: Kevork Djansezian (Getty Images)
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Ava DuVernay is an output machine at this point. From helming projects like the award-winning docuseries When They See Us and television show Queen Sugar, to directing films like Selma, Ava has her hands in so much stuff I just assume that when I see new, dope blackness on my screen that she has had something to do with it. From documentaries about social justice to shows illuminating the black experience, DuVernay is a masterclass in content creation and we’re all better for it.



John Singleton Award for Black Excellence in Directing Excellent Blackness

Winner: Robert Townsend

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Photo: Matt Carr (Getty Images)
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So many iconic black films are productions from Robert Townsend. From The Five Heartbeats to Meteor Man, to Hollywood Shuffle and BAPS, Robert Townsend is a man who wears nearly all hats involving filmmaking. The black community is all the better for it.



Richard Pryor “Oh, You Funny AF” Award for Best Black Comedian

Winner: Dave Chappelle

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Photo: Alex Edelman (AFP for Getty Images)
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No surprise here. Dave Chappelle has become the most significant comedian of our era in Black America. He brought us Chappelle’s Show and countless comedy specials that put up a mirror to society and our relationship to the ideals and values we uphold. Chappelle has become the go-to black comedian for various reasons and, ultimately, he has earned his spot in the hearts and minds of Black America as a voice of the people.