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Music Documentaries to Binge Over Your Holiday Break

No matter what your favorite genre of music is, the Boardroom family has something for you. Join us as we break down some of our favorite music documentaries of all time.

If you are a music fan, there are few things better than going behind the scenes of your favorite artist’s extravagant lifestyle to bring an additional level of understanding to their music.

In 2023, two of the world’s biggest stars did just that. Taylor Swift and Beyoncé re-wrote the record books in nearly every facet of music business. Both global superstars brokered deals with AMC to bring their fans with them on tour. “Taylor Swift: The Eras Tour” and “Renaissance: A Film by Beyoncé” each offers fans an inside look at their respective global tours. In addition to extending their global reach, the movies brought out casual and super fans alike to revel in the artistry that makes theirs among the most coveted tickets on earth.

But those are only two of countless music films. Amidst the holiday hustle, the perfect escape can take the form of an music documentary. So, the Boardroom team gathered some of our personal favorites for you to add to your queue this season.

Let’s break them down.

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Boardroom’s Favorite Music Documentaries

Trainwreck: Woodstock ’99 

I think I’ve proven that True Crime is truly my genre, but “Trainwreck: Woodstock ’99” on Netflix had me glued to the TV. I’ve heard a lot about this event, and how it so badly wanted to recreated and exceed expectations from the 1969 Woodstock music festival, but that didn’t happen.

The three-part docuseries looks back on Woodstock ’99 and draws attention to how the violence and riots unfolded. There are plenty of interviews and more footage than I would have expected from that time. I think my favorite realization from the docuseries is that Woodstock ’69 was more focused on the hippy era of music, while Woodstock ’99 drew a crowd more into heavy metal and rock music. There was truly a transformation across the industry at that time.

Michelai Graham

Dave Chappelle’s Block Party

This is not new by any stretch of the imagination, but the 2005 film “Dave Chappelle’s Block Party” is one of my favorites of all time. The doc goes behind the scenes of an epic impromptu daylong festival deep in Brooklyn arranged by … you guessed it … Dave Chappelle.

The show happened in the middle of “Chappelle’s Show’s” iconic run. The program fused hip-hop and entertainment, and this one-day event followed in those tracks. From Erykah Badu to The Roots, Kanye West to Mos Def, everyone showed up. The film was also supposed to feature a Lauryn Hill set, but she was in the midst of a dispute with Columbia Records so instead she reunited The Fugees for the first time since she went solo. The most eagle-eyed viewer will even spot a then-unknown J. Cole lurking in the crowd.

I remember bringing my unconvinced pal to see this at the Coolidge Corner Theater in Boston and she literally danced her way out of it. All in all, just a real feel-good time, and one of the greatest soundtracks of all time.

Bernadette Doykos

Summer of Soul

We all know Questlove as one of the preeminent historians of hip-hop. His 2021 project “Summer of Soul” not only solidified that, but also deepened my knowledge of the Harlem Cultural Festival.

Happening concurrently with Woodstock, the 1969 Harlem Cultural Festival was a series of six free Sunday concerts in the summer that functioned to be a positive and refreshing force in the Black community. It would have been an unfortunate lesson in cultural erasure had the Roots co-founder not initiated a restoration. The likes of Stevie Wonder, Nina Simone, the Staple Singers, Gladys Knight and the Pips, Sly and the Family Stone, the Fifth Dimension, Mahalia Jackson, and more each performed in front of roaring crowds, making “Black Woodstock” one the single most necessary events to understand our long-standing impact on entertainment. 

Vinciane Ngomsi

Thriller 40

“Thriller 40” on Showtime is awesome on so many levels.

Sonically, it’s the best pop music ever made in its purest form from raw vocals to demo construction. Not to mention that it changed the game for music videos. Visually, it’s a trip to see iconic Michael Jackson moments remastered to today’s standard.

Lastly, the office interviews with MJ in the ‘80s oddly show just how similar his speaking cadence when discussing business and creating is to Jay-Z.

Ian Stonebrook

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