Ever since the dawn of recorded music and motion pictures, musicians have often dabbled in the film industry, a lot of them trying their best to cross the G and O off of their coveted EGOT checklists. That said, the Oscar is one of the hardest awards to win for many contemporary artists. And this year five-time Grammy winner Questlove is moving along what could be a nearly unprecedented route to Oscar glory: Best Documentary Feature for “Summer of Soul.”
Perhaps the easiest route for a musician at the Oscars is through their songs for films, like past winners H.E.R. (“Fight for You” from “Judas and the Black Messiah”), Adele (the title theme from “Skyfall”), and Bob Dylan (“Things Have Changed” from “Wonder Boys”). Others might try shooting for the acting categories, like Cher (who won for “Moonstruck”) or Lady Gaga (who was nominated for acting but won for songwriting for “A Star is Born”). And there’s also ambitious ones like Prince (“Purple Rain”) and Trent Reznor (“The Social Network” and “Soul”) who earned Oscars for doing whole scores for films.
You don’t usually see musicians go down the path of nonfiction directing. “Summer of Soul (…Or, When The Revolution Could Not Be Televised)” is Questlove’s passion project. The documentary focuses on the 1969 Harlem Cultural Festival and its legacy more than 50 years later. It has been one of the most acclaimed documentaries of the season, holding an almost-perfect Rotten Tomatoes score, and it’s been sweeping the critics’ awards, including a clean sweep at the Critics Choice Documentary Awards. The film has also been awarded by groups like the National Board of Review and the Los Angeles Film Critics Association. “Summer of Soul” is additionally leading the odds to win the Grammy for Best Music Film according to Gold Derby users as of this writing, where it faces off against Bo Burnham’s massive comedy special “Inside,” as well as Grammy darling Billie Eilish’s concert film, “Happier Than Ever: A Love Letter to Los Angeles.”
If it were to win the Grammy, could this bring Questlove a step closer to the Oscar? So far, “Summer of Love” places second in the Oscar odds for Best Documentary Feature, behind the animated film “Flee.” However, an animated documentary has never won. “Flee” is also not an English-language film, which would make it an even rarer winner in the category. So it is entirely possible for “Summer of Soul” to jump to number-one, especially with its substantial esteem. And it could help that it focuses on icons of the past like Nina Simone and Stevie Wonder, resonating with older members of the motion picture academy.
If “Summer of Soul” were to win at both the Grammys and the Oscars, it’d join only two other films that have won the Grammy for Best Music Film and the Oscar for Best Documentary Feature. The first to do this was “20 Feet from Stardom,” a documentary about the lives of background singers, in 2015. “Amy,” a biographical account of Amy Winehouse’s life, career, and struggles with addiction, became the second documentary to do this shortly after, winning in 2016. Both of those examples were quite recent, so there’s precedent.
But while “Amy” and “20 Feet from Stardom” were directed by established filmmakers, this is Questlove’s first directing work, and he isn’t as well known in the film world as in the music business. Perhaps that’s what would make “Summer of Soul” such a glorious win, though. At its core, it would be a win based on passion and a way to honor the outstanding filmmaking as well as the music and artists who shaped and redefined the musical landscape of the past 50 years, despite so often being swept under the rug.
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