The 15 Best HBO Documentaries Of All Time – TVLine

For decades, HBO has been at the forefront of prestige television, producing some of the most widely lauded series and specials in the industry. This impressive distinction extends to the network’s library of original documentary programming, including limited series and films. The documentary division of HBO has long been a staple for the premium cable channel’s original output and has only grown since then. These documentary projects cover a wide range of topics, from public figures and scandals to true-crime investigations and overlooked subject matter.

Simply put, there is something for everyone among HBO’s extensive catalog of original documentaries. Here are the 15 best HBO docs of all time, all of which are currently available to stream on HBO Max.

If the original Woodstock music festival in 1969 was a celebration of peace and love, its follow-up in 1999 was mired in infamy on virtually every front. The lead-up to the festival, its three-day duration, and the aftermath are spotlighted in “Woodstock 99: Peace, Love, and Rage.” Powered by a line of interviews of popular musicians from the era and those connected to the event and music industry, the documentary explores where everything went wrong. More than just recounting the disastrous festival, the movie presents the catastrophe as a portent for the industry and nation at a pivotal point.

“Woodstock 99: Peace, Love, and Rage” came out shortly before Netflix’s own original documentary about the incident, “Trainwreck: Woodstock ’99,” with the HBO project the superior of the two. The HBO documentary provides an unflinching look at the festival, while weaving a deeper message about the zeitgeist surrounding it. “Woodstock 99” would kick off an entire HBO documentary series focused on different musical subject matter under the title “Music Box.” As an examination of the corporate co-opting of music’s most iconic festival and the consequences that came with it, “Woodstock 99: Peace, Love, and Rage” will leave viewers shaken.

There was a time when the Rolling Stones were considered the most dangerous rock ‘n’ roll band in the world, with that notoriety fueled by open debauchery. The band’s rollicking heyday is the subject of the 2012 documentary “Crossfire Hurricane,” which was co-produced by Rolling Stones members Mick Jagger, Keith Richards, and Charlie Watts. Featuring interviews played over archival footage, the movie traces the Stones’ early days in England through their continued success in 1981. Anecdotes include the death of founding member Brian Jones, the disastrous 1969 concert at Altamont, and Richards’ extensive drug use for the band’s first two decades.

Even with three of the Rolling Stones as producers, “Crossfire Hurricane” is a no-holds-barred look at the band’s origins and wildest years. The documentary is surprisingly graphic in its on-screen depiction of drug use and sexual acts that fueled the Stones’ illicit reputation for decades. But beyond the bad-boy antics, the movie shines a light on the band’s history like no other documentary has or has since. A must-watch for any Rolling Stones fan, “Crossfire Hurricane” is certainly not a sanitized look at the iconic group.

The opioid epidemic is one of the most devastating drug-fueled crises impacting Americans for the past two decades. The 2021 two-part documentary “The Crime of the Century” highlights how the country was rocked by OxyContin and fentanyl’s role in the spread of opioid misuse in the United States. The movie chronicles how the powerful pharmaceutical companies positioned their drugs, including convincing physicians to over-prescribe them to patients. The documentary also implies that people working in the federal government were allegedly complicit in these unethical business practices.

Watching “The Crime of the Century” will likely fill you with a righteous frustration about the grave injustices that are still carried out, fueling the opioid epidemic. The documentary explores everything from the wealthy families behind these pharmaceutical companies to the everyday Americans nationwide affected by the corporate malfeasance. From leaked documents to whistleblower reveals, the filmmakers unveil a system leaning into outright predatory manipulation of the vulnerable.

McDonald’s annual Monopoly promotion, encouraging customers to get winning sets of pieces for numerous prizes, has been a fast-food tradition since 1987. However, one of the figures at an agency that ran the contest for McDonald’s was revealed to be scamming the promotion from 1989 through 2001. This long-standing fraud operation is revealed in the 2020 limited series “McMillions,” examining how Jerry Jacobson recruited a system of accomplices to rig the promotion’s cash prize winnings. Jacobson’s scheme is juxtaposed with the FBI’s investigation into the matter after receiving an anonymous tip about the ongoing scam.

As far as true-crime documentary subjects go, the McDonald’s Monopoly scam is one of the more ridiculous, but no less intriguing, making it a welcome respite from the usual doom and gloom of the true-crime genre. All the colorful personalities behind such an elaborate scheme are present, as are the investigators who eventually busted the criminal operation. Across six episodes, the inner workings of this multi-year scam are depicted, with the reminder that, as ludicrous as it sounds, this really occurred.

Influential filmmaker Woody Allen’s legacy has forever been tainted by allegations of sexual misconduct and his controversial marriage to Soon-Yi Previn. Among the scandals that Allen has endured are accusations of sexually molesting Dylan Farrow, his adopted daughter with longtime partner Mia Farrow, in 1992. The allegation and its fallout over the subsequent years are covered in the 2021 limited series “Allen v. Farrow.” The series includes interviews with the Farrows and friends, recorded calls between Mia and Allen, excerpts from Allen’s 2020 memoir, and an analysis of recurring improper relationships in his films.

Unfolding in four episodes, “Allen v. Farrow” focuses on Dylan’s side of the story, in no small part because Allen and Previn reportedly declined to participate. With that in mind, there is an enormous amount of detailed analysis and archival records on display supporting the allegation. That might make the argument presented by the documentary feel understandably one-sided, but it’s clear that the filmmakers did a substantial amount of research. A complete reframing of Allen and his legacy, “Allen v. Farrow” delves into one of Hollywood’s most controversial and disturbing scandals.

Perhaps the most notorious amusement park in American history, Action Park was a water park that was open from 1978 to 1996. The establishment’s penchant for reckless attractions that got its guests injured and, in some cases, killed, is explored in the 2020 documentary “Class Action Park.” Founded in New Jersey by legally embattled businessman Eugene Mulvihill, the park’s lack of safety measures and cost-cutting operations led to numerous accidents on-site. The documentary recounts the history behind Action Park and Mulvihill, including interviews with attendees and family members of its victims.

With its ludicrously dangerous rides and slides and complete lack of care, Action Park’s legacy is played for slapstick laughs for most of the movie. This, of course, offers some tonal whiplash when “Class Action Park” reminds its audience that actual people died there. But this is a story that does come with a human cost, and the doc knows precisely when to lean into that.

Paul Reubens was one of the most successful children’s show hosts, though his career was marred by public scandals. Reubens’ legacy, particularly that of his beloved persona Pee-wee Herman, is depicted in the 2025 limited series “Pee-wee as Himself.” Reubens was interviewed by director Matt Wolf about the origins of his career and creation of the Pee-wee character, though the conversation often turned combative over Reubens’ lack of creative control. Though Reubens refused to discuss the scandals that tarnished his reputation and work, interviews with friends and colleagues shed light on the subject.

Just like the man and legacy that the documentary covers, “Pee-wee as Himself” is a complicated and complex look at Reubens. Though the series certainly celebrates Pee-wee Herman and his impact, it’s far from a rehabilitative puff piece for its subject. The documentary provides a more honest depiction of Reubens than had been done before, ending on one last revealing phone message from him to Wolf. In light of Reubens’ death in 2023, “Pee-wee as Himself” remembers him as a flawed and vulnerable human in conjunction with his pop culture legacy.

As far as digital startups go, MoviePass seemed like a no-brainer, offering users the chance to attend numerous movie screenings as part of their subscription. Of course, after a successful launch, the service suffered a catastrophic collapse due to its structure and reaction from theater chains and studios. The rise, fall, and relaunch of MoviePass is chronicled in the 2024 documentary movie “MoviePass, MovieCrash.” The documentary depicts the service’s founders, Stacy Spikes and Hamet Watt, being ousted from the company they created and the disastrous business decisions that led to its collapse.

There is something about a rise-and-fall narrative that’s inherently captivating within the documentary space. “MoviePass, MovieCrash” is no different in this regard, with the movie sparing no expense in highlighting poor practices and strategies that doomed the initial subscription service. But more than reveling in the implosion of the service, the documentary reveals how much worse the downfall of MoviePass truly was. Through its telling of modern industry hubris, “MoviePass, MovieCrash” is an informative look at an entertainment trainwreck.

The rise and fall of tech entrepreneur Elizabeth Holmes and her medical technology company Theranos is covered in the 2019 documentary “The Inventor: Out for Blood in Silicon Valley.” The film depicts Holmes and her business partner, Sunny Balwani, proclaiming Theranos to be a landmark entity out to completely revolutionize medical tech. Beyond this glossy exterior, of course, is a company run by backstabbing and paranoia, but little actual results in terms of tangible advancements. The documentary includes interviews with former Theranos employees and investors reflecting on the company’s culture and ultimate collapse.

“The Inventor” is a portrait of charismatic corporate figures who have drunk their own self-aggrandizing and delusional Kool-Aid. Holmes is the cipher to the entire story, with a considerable amount of the documentary spent trying to comprehend her and her outlook. A cautionary tale of unchecked greed in Silicon Valley, “The Inventor” feels just as vital now as it was when it premiered.

Austin, Texas, was rocked by a quadruple homicide in a frozen yogurt shop that claimed the lives of four teenage girls in 1991. This unsolved crime is the subject of the four-episode limited series “The Yogurt Shop Murders,” directed by Margaret Brown. Released in 2025, the documentary includes interviews with the families and friends of the victims, along with the investigators of the open case. More than just focusing on the crime itself, the series explores the lingering trauma and grief from the horrific incident more than 30 years later.

Though Brown goes into great detail recounting the titular crime and its subsequent investigation, the true-crime element of the documentary isn’t the point. Instead, the series is really about the aftermath and its continuing impact on those left behind in the tragedy’s wake. This is the story of how an incident this shocking affects an entire community for years afterward. There is a genuine empathy to “The Yogurt Shop Murders” that, unfortunately, so many other true-crime projects exploitatively lack.

One of the most celebrated filmmakers in Hollywood history is Steven Spielberg, who has been captivating movie audiences for more than 50 years. The 2017 documentary “Spielberg” examines its titular subject’s life and career, featuring dozens of interviews from those who know him best. This includes everyone from his family to frequent collaborators like John Williams, Harrison Ford, Tom Hanks, and Robert Zemeckis. These accounts detail Spielberg’s childhood and career beginnings to his status as a powerhouse director and producer who has influenced movies and television for decades.

“Spielberg” shines a thoroughly revealing light on the mastermind behind genre-defining blockbusters and someone who reshaped the box office on multiple occasions. Through all the epic film productions and career highlights, Spielberg himself is driven by a complete love of the medium, both as a creator and fan. For anyone who loves Spielberg projects, the documentary is an invaluable watch, given the treasure trove of behind-the-scenes footage and insight.

The 2020 limited series “I’ll Be Gone in the Dark” takes a unique approach to the well-worn true-crime documentary genre. The series follows author Michelle McNamara’s obsession with the Golden State Killer, who terrorized Northern California in the ’70s and ’80s. Researching the unsolved case extensively, McNamara digs into vast archives of old clues to try to ascertain the serial killer’s identity. After McNamara’s sudden death from an accidental overdose, her work was finished by several figures, including her husband, Patton Oswalt, with the resulting nonfiction book helping to finally close the case.

More than just a television adaptation of McNamara’s posthumously published book, “I’ll Be Gone in the Dark” was a game-changer for the genre. Rather than providing the portrait of a killer who remained at large for decades, the documentary is really a portrait of McNamara herself, unveiling her exhaustive work in bringing a murderer to justice. A meditation on obsession and grief, “I’ll Be Gone in the Dark” remains a singular achievement in the true-crime genre.

Years before ESPN consistently delivered eye-opening sports documentaries with its “30 for 30” series, HBO in 1994 produced one of the best sports documentary movies ever made. “Hoop Dreams” traced the journey of two high school basketball players in the Chicago area, William Gates and Arthur Agee, starting with both teenagers’ recruitment to the predominantly white high school St. Joseph in 1987. Gates and Agee dream of one day going pro, but as the two players’ high school careers progress, they face injuries and contentiously high-stakes games while enduring changes in their respective home lives.

“Hoop Dreams” is a sobering look at the years when youthful enthusiasm and idealism collide with the uncompromisingly harsh realities of life. In just under three hours, the film covers so much ground, including a revealing look at teenage life, the realities of racial dynamics, and the intensity of high school sports. The story may be heartbreaking, but there is a subtle sense of triumph in how determined its two primary subjects are.

For decades, the inner workings of the Church of Scientology and its activities were shrouded under a heavy veil of secrecy and the threat of legal action. Lawrence Wright’s 2013 nonfiction book “Going Clear: Scientology and the Prison of Belief” exposed and systematically deconstructed a lot of the religious organization’s practices and tenets. Filmmaker Alex Gibney adapted the book into an HBO documentary movie in 2015, putting the secretive organization under close scrutiny. This includes interviews with former Scientologists, a detailed profile on its founder, L. Ron Hubbard, and a history of alleged misconduct and abuse carried out by its members.

“Going Clear” is one of the most incisive and incendiary explorations of a religious organization covered in a documentary. The deep dive unveils an organization that is equal turns sinister and completely outlandish, with the documentary emphasizing how ridiculous some of the church’s core tenets are. The final product is an unsettling depiction of blind faith and an insidious abuse of power fueled by insatiable greed.

Real estate heir Robert Durst was a person of interest in three different murder cases — starting with the disappearance of his first wife, Kathie, in 1982 — but he was never convicted. Decades later, Durst agreed to be interviewed by filmmaker Andrew Jarecki, which became the primary material for the 2015 documentary series “The Jinx.” The program recounts the three murders linked to Durst, juxtaposed with his interviews, before new evidence and an accidental confession by Durst expose his guilt. The second season in 2024 details Durst’s conviction and life in prison, complete with additional interviews recorded from calls during his sentence, ending with his death in custody in 2022.

Durst’s unwitting confession, on a hot mic while in the bathroom, still goes down as one of the most shocking moments in any true-crime documentary. Even before that season-ending twist, “The Jinx” is a tightly crafted docuseries that expertly explains Durst and the controversies around him. This makes those bombshell revelations toward the end of its first season all the more impactful when they do come into play. A close look at one of the strangest and most manipulative figures in true crime, “The Jinx” inadvertently made history on the subject it was exploring.