3 stunning HBO Max documentaries to watch this weekend (November 7-8)

Published Nov 7, 2026, 9:15 AM EST After graduating from Marist University with a degree in communications and journalism, Dan Girolamo has over 10 years of experience writing about entertainment and sports. Dan's work can be seen in various publications, including Digital Trends, SportsCasting, and Tom's Guide. Throughout his career, Dan has interviewed several high-profile filmmakers and creatives, including Brendan Fraser, Jamie Lee Curtis, Caitriona Balfe, Frank Grillo, Miranda Cosgrove, Jai Courtney, Chris Columbus and James Cameron. Dan joins How-To Geek as a Senior Editor. When he's not writing about entertainment, Dan is either watching a movie or praying for the New York Knicks to win a championship. Like the other popular streaming services, HBO Max added many new shows and movies to its service. The Gilded Age made its triumphant return for its fourth season last weekend. As for movies, HBO Max loaded up its holiday hits collection with Elf, National Lampoon's Christmas Vacation, and The Polar Express. On the documentary front, one of our selections premiered two months ago. It's a murder mystery case, so fans of true crime will be happy with the subject. The next documentary is a comedy series that has Nathan Fielder attached as an executive producer. Finally, my top selection of the week is a basketball story that might be the defining documentary of the 1990s. 3 A Killer Story Can two amateur detectives save a convict? True crime is an American obsession. HBO Max, Netflix, Hulu, Paramount+, and Peacock—name the streaming service, and odds are they have a dedicated section for true crime movies and series. Whether it's something serious like a murder mystery or a trivial matter like an unruly neighbor, audiences have proven they will watch anything on the true crime spectrum. HBO Max, in particular, has put out several headline-making docs, including The Jinx. Speaking of a murder mystery, A Killer Story is the latest HBO Max documentary that might put your mind into a pretzel. How many times have you tried to act like a detective and solve a case while watching a documentary about a violent crime? That is what Eileen Umbehr and her husband, Keen, essentially did from their couch. In 2002, Dana Chandler was accused of killing her ex-husband and his girlfriend. Due to a lack of evidence, Eileen and Keen were not convinced that Dana committed the murder, so they emailed journalist Joe Sexton about their frustration. 2,714 emails later, Sexton finally looked into the case, and what he found isn't black and white. A Killer Story explains the entirety of the case and the three trials that Chandler would face. Filmed over six years, it's a fascinating look into a complicated case full of multiple storylines, legal malpractice, and the power of citizen journalism. If you're watching complex cases and think you might be able to help, A Killer Story might be your inspiration. A Killer Story 2 How To with John Wilson Strange yet endearing How many of you are fans of Fielder? The Canadian comedian is best known for the Comedy Central show Nathan for You. However, he's currently the talk of Hollywood thanks to You Can See Everything, his documentary about the notorious CEO of Theranos Elizabeth Holmes. Why am I bringing that up right now? Well, Fielder met fellow filmmaker John Wilson in 2018, and the two have been collaborating ever since. In 2020, Wilson released the comedy documentary series How To with John Wilson, with Fielder attached as an executive producer. In the series, Wilson sets out on a "mission of self-discovery, exploration, and observation." Unlike Fielder, who is in front of the camera on his shows, Wilson goes behind the camera and films everything POV, providing voice-over when he sees fit. Wilson's mission is fairly simple: give people advice and information on minuscule, sometimes inconsequential topics. When I say simple, I really mean mundane things, topics like how to be spontaneous, how to find a public restroom, how to make small talk, and how to put up scaffolding. There is an endearing quality about Wilson. He has this childlike inquisitive nature that is so fun to watch. Frankly, I'm asking a lot of the questions Wilson asks. If you like Fielder's comedy, then you'll appreciate Wilson's deadpan nature. 1 Hoop Dreams A literal masterpiece They certainly don't make documentaries like Hoop Dreams anymore. We're currently in an era of celebrity-focused documentaries, where the main subjects profit off their participation. While I don't blame them for snagging an EP credit and collecting some cash, it does make me think differently about the documentary. Is the subject determining what can or can't be said? Probably. It ruins the spirit of a documentary. I don't have any of those doubts with Hoop Dreams, Steve James' 1994 masterwork about two African-American high school basketball players—William Gates and Arthur Agee—with aspirations to play in the NBA. In 1987, Gates and Agee are recruited to play at a prestigious high school outside of Chicago. The boys come from low-income communities, so attending the school will take time, sacrifice, and money they don't have. The boys start school together but quickly wind up on different paths. Any basketball fan will love Hoop Dreams. It's a story about two underdogs from inner-city neighborhoods who strive to achieve their dreams. However, Hoop Dreams is more than a documentary about watching two teens put the ball in the basket. It's an examination of race and wealth disparity in America, as Gates and Agee attempt to overcome nearly impossible odds of success. You don't have to like basketball to appreciate this documentary, with the great Roger Ebert calling it "one of the great moviegoing experiences" of his lifetime. More movies and shows to check out this week If you don't know what to watch this week, then you've come to the right place. Black Doves and Stick are two shows with new seasons that recently premiered. Elsewhere, The Uprising on Peacock is the new movie I want to check out on streaming. Subscription with ads Yes, $10.99/month Simultaneous streams 2 or 4