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3 Must-Watch HBO Max Shows You Need to Stream in October 2025

by DigestWire member
October 3, 2025
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3 Must-Watch HBO Max Shows You Need to Stream in October 2025
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As the leaves change and the air turns crisp, there’s nothing better than curling up with a new series to binge.

If that’s your vibe this October, HBO Max might be the perfect platform for you.

In addition to the premieres of original comedy and drama series, the Watch With Us team is also highlighting the return of an underrated Mexican gem we think deserves more attention.

From chilling horror to sharp satire, these are the new and returning HBO Max shows worth streaming in October 2025.

‘Vgly’ — Season 2 (October 9)

Fall TV Preview 2025: 37 Picks, From ‘Nobody Wants This’ to ‘Boston Blue’

This underrated Mexican comedy series hasn’t quite broken through to American audiences yet, but it feels like a mix of Atlanta, Reservation Dogs and Dave with a style all its own. The show follows a young rapper and singer, self-styled as “Vgly” (Benny Emmanuel), as he assembles an entourage from the streets of Mexico City and tries to make it in the music industry.

Expertly blending humor with drama, music and cultural specificity, Vgly is a unique show that we’re thrilled to see return for season 2 — especially after season 1’s cliffhanger ending.

‘The Chair Company’ — Season 1 (October 12)

15 Must-Watch HBO Max Sitcoms to Stream Right Now (September 2025)

Tim Robinson and Zach Kanin, the cringe-inducing duo behind I Think You Should Leave and Detroiters, present a new comedy about William Ronald Trosper (Robinson), a businessman who thinks he’s uncovered a criminal conspiracy after being promoted at his company — or maybe he’s just imagining it?

Lake Bell costars as Trosper’s wife, and the cast also includes Lou Diamond Phillips and IT actress Sophia Lillis. Executive produced by Succession creator Adam McKay, The Chair Company looks chaotic, absurd and hilarious in the way Robinson and Kanin do best.

‘IT: Welcome to Derry’ — Season 1 (October 26)

‘IT: Welcome to Derry’ Is My Most Anticipated Fall 2025 TV Show Right Now

For horror fans, no series this fall is more hotly anticipated than this It prequel about the origins of Pennywise the Dancing Clown (Bill Skarsgård) and his reign of terror over the town of Derry, Maine. The story follows Charlotte and Leroy Hanlon (Taylour Paige and Jovan Adepo) as they move to Derry with their son just as local children begin to vanish.

Created by IT (2017) director Andy Muschietti, Welcome to Derry promises dread-inducing visuals, heartfelt performances and the chilling mythology that made the films such a hit.

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