3 entertaining HBO Max documentaries to watch this weekend (October 23-25)

Published Oct 22, 2026, 6:00 PM EDT 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. HBO Max is always producing quality content. I recently enjoyed Lanterns, the DC Universe show that played like a season of True Detective. The streamer also has some riveting documentaries, including A Killer Story, one of the best docs released in September. I have a few documentaries for those looking to watch something this weekend. With the NBA back, there is an inspiring story about a player who had a magical run at Madison Square Garden. The second documentary involves a Grammy-winning singer gone too soon. Finally, my top selection of the week features a polarizing entrepreneur currently serving time in prison for her crimes. All three documentaries are available to stream in the U.S. 3 38 at the Garden Jeremy Lin's magical run It's a good time to be a Knicks fan. After 53 long years, the New York Knicks finally ended their championship drought by winning the NBA title last spring. The city has never felt more alive. You can't walk more than a few blocks without seeing a Knicks hat or shirt. Things weren't always this good. In fact, there wasn't much to smile about for Knicks fans during the first 20 years of this century. One moment of happiness can be described with one phrase: Linsanity. In December of the 2011–12 NBA season, the Knicks claimed point guard Jeremy Lin off of waivers. Lin played at Harvard before spending time with the Golden State Warriors during the 2010–11 season. Lin was not expected to play for the Knicks, but coach Mike D'Antoni gave Lin a chance to play in February 2012. Lin thrived in his first game, setting career highs with 25 points, five rebounds, and seven assists. Shortly after Lin's breakout performance, he moved into the starting lineup, and the Knicks went on an impressive winning streak. Lin's celebrity status soared as Linsanity became a phenomenon. 38 at the Garden examines Lin's meteoric rise to the top of the sport. As someone who saw Lin play during Linsanity, I can say he gave Knicks fans something to cheer about. It all culminated in a showdown against Kobe Bryant and the Los Angeles Lakers. On behalf of all Knicks fans, I want to thank Lin for those magical few weeks in the Big Apple.​​​​​​​ Subscription with ads Yes, $10.99/month Simultaneous streams 2 or 4 2 ​​​​​​​Amy A difficult portrait of a tragic figure When discussing Amy Winehouse, it's difficult not to start at the end of her story, which concludes with her death from alcohol poisoning in 2011. Winehouse was only 27. It's a tragic ending for an exquisite musician from London. We might know how it ends, but how did it all start? Director Asif Kapadia investigates the meteoric rise and heartbreaking fall of Winehouse in the documentary Amy. Kapadia's documentary explores Winehouse's childhood and continues through her teenage years, when she started to gain recognition for her sensational voice. In 2003, Winehouse broke through with her debut album, Frank, before reaching new heights in 2006 with Back to Black. With Back to Black, the 24-year-old Winehouse won five Grammy Awards, including Best New Artist. Winehouse had all the talent in the world, but she also struggled with personal demons. Amy features interviews with Winehouse's friends and family that help paint a picture of the tortured artist. You hear beautiful renditions of Winehouse's songs with that signature rasp in her voice. You also learn about Winehouse's struggles with alcohol, drugs, addiction, bulimia, and abusive relationships. Kapadia went on to win the Academy Award for Best Documentary Feature. Watch Amy now before it leaves HBO Max on October 31. Amy Release Date July 2, 2015 1 The Inventor: Out for Blood in Silicon Valley The legend of Elizabeth Holmes Love her or hate her, Elizabeth Holmes moves the needle. Granted, she's been depicted as a compulsive liar in various books, documentaries, and shows. What isn't up for debate is the fact that she committed crimes—Holmes was convicted on multiple counts of investor fraud and originally sentenced to over 11 years in prison. The sentence was subsequently reduced, and she is currently incarcerated in Texas. But let's take it back to how Holmes became one of the most ambitious figures in Silicon Valley. Alex Gibney's The Inventor: Out for Blood in Silicon Valley takes a deep dive into Holmes's story and her rise to the top of the tech world with her company Theranos. Holmes's company claimed that it had developed rapid blood tests using small amounts of blood obtained through a finger prick. As you learn in the documentary, Theranos's technology was fraudulent, and Holmes and her associates raised money through fraud. It's the perfect time to revisit The Inventor because a new documentary about Holmes is sweeping the nation. You Can See Everything is directed by Lance Oppenheim and Nathan Fielder, and the film picks up weeks before Holmes heads to prison. You Can See Everything made $15 million during its opening weekend in limited release, and it's heading into more theaters soon. Trust me, it will be the most unique and puzzling movie you'll see all year. What else is on HBO Max? I feel like I'm always pressed for time, so I'm looking for short shows. Friends and Nathan for You can be downloaded to your phone since they are less than 25 minutes long. As for critically acclaimed HBO Max shows, you can't go wrong with Task and A Knight of the Seven Kingdoms.