The Deep Dive — Sep 30, 2026

Stiller and Del Toro Are Teaming Up Again

Ben Stiller and Benicio Del Toro are reuniting for Apple TV's Protective Custody, their first project together since Showtime's Escape at Dannemora back in 2018, where Del Toro starred as escaped convict Richard Matt and Stiller directed, both earning Emmy nominations for that work. This is also Del Toro's first-ever leading role in a comedy series. The show follows a disgraced financier accused of massive fraud who lands in protective custody and has to navigate prison politics while awaiting trial. Most outlets reporting on the project have Stiller playing that lead role, though Apple has not officially confirmed which of the two actually plays the financier.¹

I don't know much about Del Toro's comedic side, but I'm mainly excited to see another show greenlit at Apple given how stacked their lineup already is. They've already brought on a great cast: Amy Sedaris, Samson Kayo, Sonny Valicenti, and, most recently, Janeane Garofalo, a frequent Stiller collaborator going back to The Ben Stiller Show, Reality Bites, Mystery Men, and The Cable Guy.² Reporting on this one neutrally for now, but the cast alone is a reason to pay attention.

The project itself actually started as a pitch from producer Ben Silverman and Propagate Content, described early on as "Hogan's Heroes meets The Office."³ Apple then paired that concept with Mike Judge, Steve Hely, and Dave King, the same trio behind Adult Swim's Common Side Effects, with Judge also directing, his first time in the director's chair since 2009's Extract.³ Stiller is currently one of Apple's most prolific collaborators. Beyond this, he executive produces and directs episodes of Severance, stars opposite Jessica Chastain in the upcoming The Off Weeks, and has Stiller & Meara: Nothing Is Lost, his documentary about his own parents, already on the platform.⁴

Judd Apatow Lets Norm Macdonald Tell His Own Story

Norm: The Tale of Norm Macdonald, directed by Judd Apatow, premieres on Netflix October 16. It's built entirely from archival footage, personal photos, and home videos contributed by fans and friends, no talking-head interviews, no outside narrator, letting Macdonald essentially narrate his own life story.⁵

I'm a huge Norm Macdonald fan, and I first discovered him through my love of SNL. His time on Weekend Update made him one of the greatest to ever sit behind that desk, and it came with a notable firing to go along with it. Norm was pulled from the anchor chair in 1998 after refusing to let up on O.J. Simpson jokes throughout Simpson's murder trial. NBC West Coast president Don Ohlmeyer, a close friend of Simpson's, made the call, publicly citing declining ratings, though almost no one, including Norm himself, believed that was the real reason.⁶ The story of his life is sad, and I wish I had learned more about him while he was still alive.

Given how much personality Norm had, and how much time he spent in front of a camera over his career, I think this archival-only approach is a unique choice that more documentaries about famous people with that kind of footage should try. That said, it's always interesting to hear other people's perspectives on a comedian and see whether it validates things I've already thought myself, so I'm curious how much this connects with a wider audience, either incredibly well, or not at all. The documentary hasn't premiered yet, so formal reviews aren't out, but early reaction to the trailer has leaned toward exactly that idea, with viewers online noting that no impression or reenactment could ever capture his deadpan the way raw footage does.⁷

Giggly Squad Signs With SiriusXM

Hannah Berner and Paige DeSorbo's Giggly Squad podcast signed a four-year exclusive distribution deal with SiriusXM, announced September 17, reportedly worth around $160 million. The show is moving over from Acast, though episodes will stay available on YouTube and other platforms. New exclusive programming under the deal is planned for 2027.⁸

I don't listen to Giggly Squad myself, but as a fan of Summer House, I've watched this show's trajectory closely, and I never would have guessed it would grow to where it has. This podcast almost certainly played a role in helping Hannah Berner's stand-up career take off the way it has. I don't know much about podcast deals outside of the famous Rogan-Spotify one, but it's interesting to see a move like this happen in this direction. Usually we see people moving away from Sirius into other spaces, like Howard Stern heading to HBO or The Bonfire building out on YouTube and podcast platforms. Giggly Squad started in streaming and is now moving into a more traditional radio-adjacent space.

SNL's Opening Monologue Gets a Familiar Face

Ramy Youssef played Mayor Mamdani for the cold open of SNL's September 26 season premiere, his second time in the role after debuting it back in November 2025.⁹ I expect to see him back in this role regularly as Mamdani continues his term.

Production News on The Burbs

Peacock renewed The 'Burbs, starring Keke Palmer and Jack Whitehall, for a second season back in April 2026, following a blockbuster debut that racked up 1.7 billion viewing minutes.¹⁰ Production on Season 2 has now officially begun, per a recent social media announcement.

Season 1 was great because of a stacked cast, so even if I'm not particularly invested in where the story goes, I'm going to tune in for Season 2 regardless.

Yellowjackets Sets Its Final Season

Yellowjackets was renewed for a fourth season on May 20, 2025, and confirmed as the show's final season that October. The Season 4 premiere date, November 20, was announced on August 20, 2026. The final season streams on Paramount+ with the Premium plan before it airs on Showtime.¹¹

I watch this show exclusively on Netflix, so it'll be a while until I get to see it for myself. All I'm asking for is some real resolution, even if it's not a happy ending.

Sources

1. The Hollywood Reporter, "Benicio Del Toro to Star in First Comedy Series Leading Role, Apple TV's 'Protective Custody'" — hollywoodreporter.com/tv/tv-news/benicio-del-toro-first-comedy-series-starring-role-apple-tv-1236653968
2. Deadline, "'Protective Custody' TV Series Casts Janeane Garofalo" — deadline.com/2026/09/protective-custody-tv-series-cast-janeane-garofalo-1237109272
3. AV Club, "Ben Stiller's getting in front of the camera for Mike Judge's new Apple comedy" — avclub.com/ben-stiller-mike-judge-apple-comedy-protective-custody
4. The Hollywood Reporter, "Benicio Del Toro to Star in First Comedy Series Leading Role, Apple TV's 'Protective Custody'" — hollywoodreporter.com/tv/tv-news/benicio-del-toro-first-comedy-series-starring-role-apple-tv-1236653968
5. Rolling Stone, "Judd Apatow Lets Norm Macdonald Speak for Himself in Netflix's 'Norm' Doc Trailer" — rollingstone.com/tv-movies/tv-movie-news/norm-macdonald-judd-apatow-documentary-trailer-1235629919
6. Rolling Stone Australia, "Norm MacDonald is Fired From 'SNL' Over (Hilarious) OJ Simpson Jokes" — au.rollingstone.com/music/music-lists/-49497/norm-macdonald-is-fired-from-snl-over-hilarious-oj-simpson-jokes-49544
7. X/Netflix, trailer reaction thread — x.com/netflix/status/2102427707522892064
8. SiriusXM, "SiriusXM Inks New Multi-Year Agreement with 'Giggly Squad' Podcast and Hosts Hannah Berner and Paige DeSorbo" — investor.siriusxm.com/news-events/press-releases/detail/2304/siriusxm-inks-new-multi-year-agreement-with-giggly
9. NBC Insider, "Ramy Youssef's Zohran Mamdani Hangs with Donald Trump in SNL's September 26 Cold Open" — nbc.com/nbc-insider/ramy-youssef-snl-trump-mamdani-cold-open-watch
10. Deadline, "'The Burbs' Renewed for Season 2 at Peacock" — deadline.com/2026/04/the-burbs-keke-palmer-renewed-season-2-peacock-1236859530
11. Vital Thrills, "Final Season of Yellowjackets to Premiere on November 20" — vitalthrills.com/final-season-of-yellowjackets-to-premiere-on-november-20