Documentaries Films Hip-Hop Rap

My Five Favorite Hip-Hop Documentaries


Documentaries – unfairly – have long been seen as a snob’s film of choice.

Instead of watching things blow up or men in capes fight evil or two people clumsily fall in love, documentaries are serious movies for serious people about serious things. That’s the only reaction when you see people speaking to (or next to) the camera and a deep voiceover filling in the exposition. The seriousness is palpable in almost every single one because of the form.

On the other hand, hip-hop is the language and music of the oppressed. It came from the streets, not from a study or an office, and while serious, it is also playful, fun, and loose.

In other words, they are quite dissimilar.

However, when combined, the two have made some wonderful art. It turns out that hip-hop is a subject that is nearly perfect for a nonfiction film. Last year, I listed my favorite hip-hop books, so this time I decided to anoint my favorite documentaries.

While there are numerous good films that focus on one specific artist or label – Welcome to Death Row, Fade to Black, Time is Illmatic, Beats, Rhymes & Life – I’ve chosen to highlight docs that take in a fuller picture and incorporate a wider swath of the culture, so none of these are single subject works.

5. Rhyme & Reason

Rhyme & Reason is one of the most ambitious hip-hop documentaries. Rather than simply capturing something, it attempts to ask probing questions, like where does hip-hop stand compared to other genres and the impact the music has on society and the culture, including its use of misogyny and violent imagery. Over 80 subjects are interviewed and the topics are both deep and varied, but questions are left hanging and it feels like a work that is only half-finished. Still, that half is compelling.

4. Dave Chappelle’s Block Party

Ever since hip-hop moved from the street corner to the corner office, it’s been much more difficult for it to remain connected with its neighborhood roots. But Dave Chappelle somehow managed to do it, organizing a concert film in Brooklyn that featured many favorites of the alternative hip-hop crowd, namely the Soulquarians. Oh, and Kanye, back when he still rocked the pink Polo and Jesus chain. It is a funny, interesting look at how a show is put on. Most of all, it’s just fun.

3. Something from Nothing: The Art of Rap

Ice-T is a hip-hop pioneer that has some classics to his name. When asked how they came about, he had the idea for a documentary on how great lyricists craft their rhymes out of thin air. Hence, Something from Nothing. While probably a bit too focused for casual fans, it is the greatest insight into the mind of some of the greatest MC’s in history, including Rakim, Eminem, KRS-One, Big Daddy Kane, Ice Cube, Nas, Treach, and many more. A great film for fans of lyrics and for those of us were once struggle rapers.

2. Stretch & Bobbito: Radio that Changed Lives

From a college station on the campus of Columbia University, two kids hosted what The Source called it the greatest hip-hop radio show of all time and never made a penny doing it. Nas before Illmatic, Jay-Z and Big L together in 1995, and Eminem before The Slim Shady LP. All of them were showcased on The Stretch & Bobbito Show. Radio that Changed Lives is not a perfect film. It doesn’t take enough time to explain background facts and breezes through important moments, but it wonderfully captures 1990s New York City hip-hop and its roster of interviews of stars – Jay-Z, Nas, Eminem, Busta Rhymes, Fat Joe – remembering their unsigned days is riveting. It’s like a time capsule of hip-hop’s second golden age.

1. The Show

There are multiple elements that make The Show such an engrossing film, but the biggest is that is presented as if the audience is simultaneously both backstage and in the front row for a massive hip-hop concert featuring some of the biggest names in the game. Between exclusive live performances, there are in-depth interviews, often in dressing rooms, with stars and legends like Dr. Dre, Snoop Doggy Dogg, Wu-Tang Clan, and The Notorious B.I.G. It is an incredibly honest piece of work – particularly in 1995 – because never before had the curtain been pulled back on the game. Dre, who at the time was only a few years removed from N.W.A, summed it up perfectly when he said, “Living up to what you say on records, it’s all entertainment. Anybody in their right mind knows you can talk about shooting somebody on a record but ain’t really go out there and do it, unless you’re just stupid. It’s entertainment, you know, we make records, it’s all entertainment, that’s all it is. This is like our jobs.” Thanks to The Show, for the first time in history, hip-hop was exposed to be a profession and an industry rather than a completely factual medium.

Christopher Pierznik’s nine books are available in paperback and Kindle. Check out more of his writing at MediumHis work has appeared on XXL, Cuepoint, Business InsiderThe CauldronMedium, Fatherly, Hip Hop Golden Age, and many more. Subscribe to his monthly newsletter or follow him on Facebook or Twitter.

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By Christopher Pierznik

Christopher Pierznik is the author of 9 books and has contributed to numerous websites on a variety of topics including music, sports, movies, TV, personal finance, and life. He works in corporate finance and lives in northern New Jersey with his family. His dream is to one day be a member of the Wu-Tang Clan.

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