Feeling overwhelmed by the endless streaming options? You're not alone. It's easy to get lost in the sea of choices and end up rewatching old favorites (no judgment if you're on a Gilmore Girls loop). But this week, HBO Max is serving up a lineup that's too good to ignore. From spine-chilling Halloween picks to cringe-worthy comedies, here’s what you should be streaming from October 13 to 19—and trust me, it’s worth stepping out of your comfort zone.
But here's where it gets controversial... Is Tim Robinson’s brand of humor too niche, or is he a comedic genius? You decide. First up, The Chair Company, a new series from Robinson and Zach Kanin, premiered on October 12. Robinson plays Ron Kasper, a middle manager whose life takes a hilariously embarrassing turn. With a stellar cast including Lake Bell, Sophia Lillis, and Lou Diamond Phillips, this show is a must-watch—even if you’re skeptical about Robinson’s schtick. And this is the part most people miss... the subtle brilliance of his off-putting characters. Chris Evangelista from /Film gave it a thumbs up (https://www.slashfilm.com/1991662/the-chair-company-tim-robinson-hbo-series-review/), so you know it’s worth your time.
Next, if you’re craving something uniquely bizarre, pair The Chair Company with Robinson’s 2024 film Friendship. Written and directed by Andrew DeYoung, this movie stars Robinson as Craig Waterman, a man so odd he makes awkwardness an art form. When he befriends his neighbor, a weatherman played by Paul Rudd, things take a wildly unpredictable turn. It’s absurd, it’s hilarious, and it’s one of the best comedies of 2025, according to /Film (https://www.slashfilm.com/1990171/best-comedies-2025/). But here’s the question: Is Craig’s bizarre behavior endearing or just plain off-putting? Let’s debate in the comments.
Switching gears, An Intimate Evening with Adam Pally premieres on October 17. This one-man special features Pally, guitar in hand, delivering jokes and ditties that are equal parts funny and risqué. I caught an early performance at 30 Rockefeller Center’s Pebble Bar, and let me tell you, it’s a wild ride. Pally’s humor is unapologetically quirky, and this special is no exception. But is it too niche, or does it hit the right notes? You be the judge.
For fans of dark, twisted storytelling, the finale of Task airs on October 19. This miniseries, from the creators of Mare of Easttown, follows FBI agent Tom Brandis (Mark Ruffalo) as he hunts down a violent burglar. The cat-and-mouse game between Tom and the culprit, Robbie Prendergrast (Tom Pelphrey), is intense and gripping. If you haven’t caught up yet, the entire series will be available to binge after the finale. But here’s the real question: Does Task live up to the hype of its predecessor, or does it fall short?
Finally, if you’re in the mood for something truly mind-bending, check out The Substance. This Mubi original, now on HBO Max, stars Demi Moore and Margaret Qualley in a story that explores the dark side of beauty and youth. Moore plays Elisabeth Sparkle, a fading star who uses a mysterious substance to inhabit a younger body—with horrifying consequences. The ending is absolutely bonkers (https://www.slashfilm.com/1668549/the-substance-ending-explained/), but is it genius or just plain disturbing? Let’s discuss.
All of these picks are streaming now on HBO Max. So, what are you waiting for? Dive in, and let’s talk about which one left you laughing, cringing, or questioning everything. Which one’s your favorite? And which one do you think deserves more hype? Let’s hear it in the comments!
