Last Updated: August 31st
More than any other genre, hip-hop was the most documented from its inception, thanks to the increased availability of recording equipment. It allowed the kids who went from drawing on walls to spinning on floors and trying out their first few rhymes to commit their experiences to cellulose in a way that wasn’t possible at the outset of rock ‘n’ roll or jazz. As engrossing as rock and pop tales can be, with rap and rappers, there are often heightened levels of drama based on the biographies of the artists and the environments that bred the genre due to the addition of guns, gangs, and organized crime that often predate or inform rap stardom.
Jay-Z was a flashy drug dealer before Reasonable Doubt gave him a route to legal money, 50 Cent was shot nine times before his resounding comeback mixtapes led to a deal with Shady/Aftermath, and Murder Inc. was shut down by an investigation into the company’s supposedly shady seed money. Meanwhile, the Notorious BIG and Tupac were granted legendary status by their untimely — and spookily timed — demises. Some stories are less dramatic, but no less earth-shaking, like the story of A Tribe Called Quest’s decade of squabbles or the foundations of hip-hop culture itself. These are some of hip-hop’s most essential documentaries; whether you’re a student of the game or just curious about how this global phenomenon became so huge, these films have something for everyone.
Rhyme & Reason
One of hip-hop’s first big documentaries, Rhyme & Reason covers much of rap’s early rise to prominence, exploring both the music’s history and some of its more controversial imagery through interviews with some of the ’90s’ biggest hitmakers, including Da Brat, E-40, Lauryn Hill, Nas, Q-Tip, and the Wu-Tang Clan.
Biggie & Tupac
Nick Broomfield explores one of the most pervasive conspiracy theories about the potentially-related deaths of two of hip-hop’s biggest stars and most compelling figures. While the results of Broomfield’s “investigation” into the theory that Suge Knight ultimately arranged the hits that took the lives of two of the genres brightest stars at the heights of their careers are inconclusive at best, he turns in 108 of the most riveting narrative surrounding the two outsized personalities ever committed to screen.
Beats, Rhymes & Life: The Travels Of A Tribe Called Quest
Shot by Michael Rapaport in his directorial debut over the course of several months with the group while on tour, the poignancy of this film is rendered all the more heart-wrenching by the fact that its final prediction came true five years later — after the death of one of its most crucial subjects. Both a celebration of one of hip-hop’s most impactful groups and an achingly hopeful plea for reconciliation, it also serves as an unwitting, but lovingly fitting eulogy to Phife Dawg after his death.
Something From Nothing: The Art of Rap
As a movie, The Art Of Rap may make for sleepy subject matter but as a technical guide on the craftsmanship and care that goes into building a verse from scratch, there is perhaps no better source for both instruction and insight. Ice-T directed and produced this film almost purely as a love letter to the craft of rapping, and anyone who’s ever tried their hand at writing a rhyme can find something here to relate to.
Dave Chappelle’s Block Party
Dedicated to the memory of late, great Detroit producer Jay Dee (aka J Dilla), who died just one month before the film’s release, the film follows both the production of and the performances from Chappelle’s 2004 block party in New York City. The borderline impromptu concert served as a precursor to annual shows like the Roots Picnic, putting several of the comedian’s favorite talents on stage at a festival-like set of performances featuring a pre-fame Kanye West and the initial reunion of The Fugees.
So, there’s “essential” and then there’s “you must watch this documentary before you can even claim to know the first thing about hip-hop, because this documentary is as close to literally being ‘the first thing about hip-hop’ as it gets.” Conduct yourself accordingly.
Fade To Black
Back when Jay-Z was pretending like he didn’t want to be a rapper anymore, he put together this doc to celebrate a career that, to the best of anyone’s knowledge at the time, was coming full circle with its final project, The Black Album. The film loses some of its punch in hindsight but still provides intriguing insight into Jay’s creative process and mindset while looking forward to an admittedly earned retirement.
While all of the focus lately has been on who’s got the best memes or gossipy dirt, there was once a time when hip-hop heads legitimately feared rap beef escalating into street violence — a fear largely born of the deaths of Biggie and Tupac. And while none of the hip-hop-adjacent tiffs covered in the first and best installment of the Beef series ever seemed directly in danger of devolving that far, it’s still a fascinating examination of the relation between neighborhood politics and those of the music business.
Time Is Illmatic
A look back at Nas’ illustrious career to date, Time Is Illmatic examines not just the creation of Nas’ first and most classic album but also the social conditions that created his then-nihilistic outlook. Featuring interviews from Nas, his brother, his father, and hip-hop luminaries who both grew up with Nas and were inspired by him, this documentary takes a hard look at the beauty and desolation of poverty, racism, and the hardship of growing up at the bottom of America’s social hierarchy.
Produced in 2000 at the height of Def Jam Recordings’ renaissance, Backstage follows the principal acts from the label’s 1999 Hard Knock Life Tour and is worth a watch if only for the epic footage of Jay-Z and DMX (and their Nation of Islam bodyguard!) freestyling in a dressing room before their career paths diverged so wildly into what we know now.
It helps to think of this one as sort of a precursor to Backstage, only from earlier in the decade, with Def Jam’s original premiere artists as its focus. LL Cool J, Run DMC, and Whodini all make appearances as director Brian Robbins and narrator Russell Simmons bridge the gap between rap’s nascent eighties and then-burgeoning early-nineties “Golden Era.”
If anyone ever complains to you about how modern rappers dress, calmly direct that person to the nearest Netflix-equipped device and make them watch this. As Sacha Jenkins (of the Rapture docuseries) chronicles the evolution of hip-hop’s fashion and fads, take care to point out to them that not only has the style evolved, but come full circle — tight jeans aren’t just a post-Millennial thing, after all.
Just For Kicks
Exploring the origins of the modern sneaker culture — before it blew up into the bot-obsessed, Ebay-flipping, blog-centric juggernaut it is today — Just For Kicks reveals how closely knit hip-hop’s pioneers and modern sneakerheads truly are.
This Is The Life
Important for two reasons: One, far too many hip-hop documentaries tend to focus on New York due to its status as the origin of hip-hop while ignoring how the developing culture resonated with folks outside of that fair city, and two, because this was the first film directed by Ava DuVernay, who would go on to direct Academy Award-winning movies like Martin Luther King biopic Selma and 2018’s multicultural adaptation of classic young adult novel A Wrinkle In Time. This Is The Life preserves an element of hip-hop history that might otherwise be buried or lost to time and it also jumpstarted the career of one of the most important filmmakers today.
Stretch And Bobbito: Radio That Changed Lives
The beginnings of many of hip-hop’s legends’ ascents can be traced back to single moments in their careers when they put the whole world on notice. For fallen legend Big L, that was his 1995 freestyle alongside Jay-Z on New York radio’s The Stretch Armstrong and Bobbito Show. But here’s the thing: That show wasn’t just the jumping-off point for Big L — it introduced the world at large to dozens of up-and-coming rappers, many before they had ever achieved any other form of mainstream exposure, and some who would go on to become some of rap’s most recognizable names and faces, like Nas, Eminem, and Wu-Tang Clan.
The Art Of Organized Noize
You gotta have love for the South. Before Future and Zaytoven set the internet on fire with their collaborative albums, before trap and Southern hip-hop dominated the primary features of the hip-hop landscape, and before Outkast was a household name, Organized Noize crafted hits for some of the biggest acts in hip-hop and R&B from an Atlanta basement fondly nicknamed “The Dungeon.” It’s fair to say that without Sleepy Brown, Ray Murray, and Rico Wade, modern hip-hop would sound wildly different, as they were instrumental to the success of Atlanta’s late-nineties takeover and Outkast’s radio takeover.