Dive into the endless sea of streaming options, and it's easy to feel paralyzed by choice—much like staring at a buffet table brimming with unfamiliar dishes when you just crave your favorite comfort food. I confess, when the evening calls for a relaxing binge, I often default to rewatching the cozy antics of "Gilmore Girls," and no one gets to criticize that! Yet, stepping outside our comfort zones can lead to delightful discoveries, and right now, HBO Max is bursting with fresh, captivating content that's worth exploring. Whether you're in the mood for spine-tingling thrills to suit the Halloween vibe—as a quick shoutout, "Bring Her Back" dropped on the platform early this month and received glowing praise from /Film's Chris Evangelista (https://www.slashfilm.com/1861370/bring-her-back-review/), delivering more gut-wrenching terror than mere freakiness—or if you're drawn to niche, awkward comedies that make you squirm and chuckle, I've curated a top five lineup to guide you through October 13 to 19.
Let's kick off with "The Chair Company," a quirky new series starring Tim Robinson, whose eccentric delivery has charmed fans through his roles in shows like the absurdly hilarious "I Think You Should Leave." Imagine a blend of Catherine O'Hara's unforgettable inflection in "Schitt's Creek"—think her iconic 'baby' line—and Robinson's knack for making a simple squint uproariously funny. He's built a career on portraying endearingly obnoxious characters who stubbornly refuse to admit fault, and this show amplifies that charm. Created with collaborator Zach Kanin, "The Chair Company" debuted on October 12 and earned a thumbs-up from /Film's Chris Evangelista (https://www.slashfilm.com/1991662/the-chair-company-tim-robinson-hbo-series-review/). Without giving away the wild plot twists, it follows Ron Kasper (Robinson), a mundane office manager, who spirals into chaos after a humiliating workplace incident—a classic setup for Robinson's personas. Supported by a stellar cast including Lake Bell as his spouse, Sophia Lillis from "It," comedy legend Jim Downey, seasoned actor Lou Diamond Phillips, and rising talent Joseph Tudisco, this half-hour comedy keeps things lively. If you're worried Robinson's style might grow tiresome, fear not; it's a must-watch for its unpredictability.
But here's where it gets controversial—do comedians like Robinson push boundaries too far with their offbeat humor, or is it a refreshing antidote to sanitized entertainment? What do you think—does embracing weirdness make comedy more authentic? I'd love to hear your take in the comments.
Next up, prepare for a one-of-a-kind treat: "An Intimate Evening with Adam Pally" arrives on October 17, and I have a personal story to share. I caught an early version of this solo act at 30 Rockefeller Center's Pebble Bar back in summer 2023, and I'm overjoyed it's now on HBO Max. This special features the "Happy Endings" star armed with a guitar, cracking jokes, strumming tunes, and dishing out 'bubbameisters'—as he put it in HBO's press release, born from a burning need to create something meaningful. Expect plenty of laughter and music, accessible to both longtime fans and newcomers. Just a heads-up, it's a tad adult-oriented, so maybe not ideal for the little ones.
Shifting gears to another Tim Robinson gem, "Friendship" (2024), directed by Andrew DeYoung—who also exec-produces "The Chair Company." Pair it with the series for a Robinson double feature. Robinson plays Craig Waterman, an extraordinarily peculiar man who spits out lines like 'I heard there's a new Marvel flick out that's supposed to be nuts' and remains unfazed when his son Steven (Jack Dylan Grazer) plants a passionate kiss on his mother Tami (Kate Mara). Enter neighbor Austin Carmichael (a spot-on Paul Rudd), a weather reporter and fossil enthusiast, sparking what could be a budding friendship. But Craig's eccentricity quickly derails it, leading to outrageous attempts to salvage the bond—moves that are both outrageous and oddly inspiring. You need to appreciate Robinson's vibe for this one, so try the series first, then this film. Oh, and /Film crowned it one of the best comedies of 2025 (https://www.slashfilm.com/1990171/best-comedies-2025/).
And this is the part most people miss—how do we define true friendship in an age of superficial connections? Is Craig's bizarre persistence admirable, or a cautionary tale? Share your opinions below; does this challenge your views on relationships?
Don't miss the October 19 finale of "Task," HBO's gripping miniseries. If you've been hooked on this dark, convoluted tale, mark your calendars for the conclusion. Brought to you by the "Mare of Easttown" team, including creator Brad Ingelsby, it revisits the Philly suburbs with thick Delaware County accents (https://www.slashfilm.com/1981053/mark-ruffalo-task-universe-hbo-crime-series-mare-of-easttown/). FBI agent Tom Brandis (Mark Ruffalo) heads a team hunting Robbie Prendergrast (Tom Pelphrey), a burglar whose crimes escalate to violence, constantly outmaneuvering Tom. Their tense pursuit builds to a climactic, unsettling resolution. If you're not caught up, binge the whole thing post-finale.
Finally, "The Substance," a 2024 Oscar nominee from director Coralie Fargeat, landed on HBO Max October 10. Perfect for Halloween or reflecting on society's obsession with women's youth. Elisabeth Sparkle (Demi Moore, in an Oscar-caliber performance) uses the titular substance to alternate bodies with a younger, 'flawless' version, Sue (Margaret Qualley), but must return weekly to her original form via IV. Yet, Elisabeth, lured by Sue's effortless lifestyle, breaks the rules. The duo's chemistry is electric, leading to a wild, body horror-laden climax—check out the ending explanation if you dare (https://www.slashfilm.com/1668549/the-substance-ending-explained/). Brace for gore, but it's a profound commentary on aging and beauty standards.
All these gems are streaming on HBO Max right now. What sparks debate here is the push for originality in comedy and drama—does it sometimes cross into discomfort, or is that the point of great art? Do you agree that stepping out of comfort zones enriches our viewing? Comment with your thoughts; I'd love to discuss!
