You Made It Weird with Pete Holmes

Episode: Josh Ruben #3

October 1, 2025

Episode Overview

The third sit-down between Pete Holmes and multi-hyphenate comedian, actor, and director Josh Ruben is a classic "silly one," packed with improv, voices, Hollywood inside baseball, and some real insights into the craft of acting and filmmaking. The conversation, peppered with character work, impressions, and meta-jokes about the entertainment industry, gradually transitions to thoughtful reflections on directing horror movies, the psychology of actors, and the cathartic function of horror in culture. Mixed throughout are tangents on psychic readings, family, and the weirdness comedians carry.

Key Discussion Points & Insights

1. Comedy, Industry Weirdness, and Impressions

• Opening Banter & Impressions (02:00–14:00)

  • Josh and Pete launch into freewheeling bits, including riffs on Alec Baldwin, Gareth Reynolds’ Jay Leno impression, following people on social media, and a running bit with "Invisalign."
  • Hilarious inside stories about meeting Philip Seymour Hoffman and the anxiety (and pride) of doing impressions in front of your idols.
    • Quote: "He was like, well done. Like, shook my arm like Shakespeare. Well done. Well done." — Josh Ruben on meeting his idol, Philip Seymour Hoffman (06:20)
  • Commentary on the new etiquette of following spouses in the entertainment world.
  • Impressions become a recurring motif, with playful debates about whether it’s “okay” to impersonate certain people.

• Residuals, Industry Struggles, and Mailbox Money (07:48–08:53)

  • Running gag about “mailbox money” (residual checks), the randomness of how actors get recognized, and the mercurial nature of fame (e.g., "Make Some Noise" vs. a whole career).
  • Industry meta-jokes about the fall of platforms like Quibi or Super Deluxe.

2. Directing, Acting, and The Art of Managing People

• Challenges of Directing (12:32–22:17)
  • Josh shares the learning curve of being a director, especially when handling “salty” (difficult) actors, and the subtleties of “manipulating” actors into necessary blocking for shots.
    • Quote: "I just. I'm still learning... and I'm starting to get good at manipulating actors into doing blocking." — Josh Ruben (12:40)
  • The contrast between authoritative directors (like William Friedkin) and a softer approach, often using humor to make suggestions or diffuse tension.
    • Quote: "I disarm with humor, which I think Mike Nichols actually did. If it starts to get weird, I'll just start singing Happy Birthday or something." — Josh Ruben (13:49)
  • Anecdotes about working with tough, detail-oriented actors like J.K. Simmons—managing their depth of preparation and nitpicks, and whether such attention to detail is a facet of their greatness.
  • Pete reflects on acting, coaching vs. learning on the job, and why some actors demand textual justification for lines or movement.
    • Quote: "It's so embarrassing to have learned so much about acting through acting." — Pete Holmes (14:55)

3. Medical Mishaps & Celebrity Lore

• Bob Odenkirk’s Heart Attack and Pop Culture (16:41–19:04)
  • Conversation about Bob Odenkirk’s on-set heart scare and the (possibly cursed) symbolism of Peloton bikes, referencing moments in media that impacted real-world company stocks.

4. Horror Filmmaking, Tropes, and Cultural Resonance

• Living With Horror (Behind the Scenes) (33:07–44:44)

  • Pete (via “Irina wants to know” segment) asks if saturating oneself in horrific imagery, as a director, has a psychological cost. Josh admits to being spooked alone in New Zealand, living in a big, quiet house after days of shooting.
    • Quote: "I was just kind of staring off and picturing this like, crudeson like, image of, you know, the killer from my film staring back at me." — Josh Ruben (34:19)
  • On the escalated impact of horror films after having kids.
  • Josh clarifies his preference for “gateway horror” (e.g., Joe Dante, John Carpenter, Scream) over “torture porn.”

• The Function and Mechanics of Horror (37:00–45:04)

  • Horror films provide catharsis and empowerment, especially to the marginalized and "othered" (queer, BIPOC, or simply “weird” or bullied kids).
    • Quote: "We watch something that's... usually normal people survive horrific situations... it's so cathartic." — Josh Ruben (38:07)
  • Pete and Josh discuss the “rules” of horror (referencing Cabin in the Woods, Scream) and how clever directors plant setups early for later payoffs.
    • Quote: "The thing that saves you can't be something you haven't seen before. The audience hates that." — Pete Holmes (44:47)
  • The ongoing obsession with horror is linked, not to cultural hopelessness, but to the satisfaction of seeing ordinary people overcome, or at least survive, chaos.

• On Directing Tropes and Editing (58:00–65:07)

  • Pete inquires: How do you keep genre tropes fresh? Josh explains the science of suspense — “lulling” the audience and then springing the scare in a rhythmically surprising but inevitable way, sometimes letting “luck” happen on set for the best reveals.
    • Quote: "The scary stuff is such a science... you're lulled into a sense of normalcy and complacency... and it's the asymmetrical moment... that's the secret." — Josh Ruben (58:23)
  • Editing as creative salvation: letting collaborators reshape moments, even cutting huge sequences into tight, energetic montages for pacing.

5. Representation, Comedy in Horror, and Personal Stakes

• Catharsis and Representation in Genre (47:27–50:03)

  • Horror is important, in part, because it lets all audiences, especially "outsiders," live out power fantasies: survival, revenge, triumph.
  • Josh talks about his own experience as a chubby, lonely kid bonding with queer and “othered” horror fans.

• FOMO and the Premise of Heart Eyes (56:53–57:45)

  • The killer in Heart Eyes embodies the bitterness of being a single person besieged by “coupleness.”
    • Quote: "You have to do that. It ends up being about something else... There’s a little bit of like, yeah, I fucking hate Valentine’s Day." — Josh Ruben (57:31)
  • The slasher is a “mascot for anti-Valentine's Day.” The film uses genre to explore feelings of exclusion and resentment in a heightened, comedic way.

• Actor-Directors in Horror, Comedy as Preparation (68:28–71:22)

  • Pete notes the trend of comedic actors (Peel, Cregger, Ruben) excelling at horror, theorizing it has to do with their attention to behavioral detail and subversive instincts.
  • Josh credits comedians’ ability to recognize minutiae in behavior, creating “safe spaces” for actors while also capturing authenticity.
    • Quote: "We get. We know the specifics of behavior... None of us get caught trying to be funny." — Josh Ruben (71:09)
  • Emotional sensitivity is presented as both a curse and a directive superpower in art.

6. Psychics, Weirdness, and Personal Rituals

• On Consulting Psychics (73:39–75:52)
  • Pete and Josh bond over their genuine belief in psychics, swapping stories about uncanny specific readings. Josh describes searching for emotional insight or affirmation from his psychic, Sunny.
    • Quote: "Her name is Sunny, she's our age, and she's actually intuitive... there's something wrong with your aunt's foot... you'd be like, whoa." — Josh Ruben (73:48)
  • Pete tells a story of a psychic nailing the nickname “Bug” for his ex.
  • Both agree: even as comedians, “something’s going on.” Josh offers to share contact info.

Memorable Quotes & Moments with Timestamps

• Philip Seymour Hoffman’s Approval:
  “He reached across like a mob boss in a big puffy coat... Well done. Well done.” — Josh Ruben (06:20)

• On Disarming Difficult Actors:
  “I disarm with humor... if it starts to get weird, I’ll just start singing Happy Birthday.” — Josh Ruben (13:49)

• On Learning by Doing:
  “It’s so embarrassing to have learned so much about acting through acting.” — Pete Holmes (14:55)

• Catharsis through Horror:
  “We watch something that’s... usually normal people survive horrific situations... it’s so cathartic.” — Josh Ruben (38:07)

• The Anti-Valentine’s Slasher:
  “There’s a little bit of like, yeah, I fucking hate Valentine’s Day... make him a bit of a mascot for anti-Valentine's Day.” — Josh Ruben (57:31)

• On Comedy-Horror Directors:
  “None of us get caught trying to be funny... if you’re a good actor, you’re not going to play a funny scream.” — Josh Ruben (71:09)

• Belief in Psychics:
  “Her name is Sunny, she's our age, and she's actually intuitive... There’s something wrong with your aunt’s foot.” — Josh Ruben (73:48)

• Keep it Crispy Sign-off:
  “What would you say? Keep it crispy, my friends.” — Josh Ruben (77:33)

Notable Segments & Timestamps

• Comic Improv, Industry Riffs, and Impressions: 02:00–14:00
• Directing and Working with Salty Actors: 12:32–22:17
• Bob Odenkirk's Heart Incident, Industry Sidebar: 16:41–19:04
• Horror Movie Craft, Film Tropes: 33:07–45:04 & 58:00–65:07
• Editing Realities, Montage Stories in TV/Film: 65:08–67:34
• Comedy/Horror Director Discussion: 68:28–71:22
• Psychic Consultation and Closing Bits: 73:39–77:41

Tone

Consistently silly, quick-paced, and meta, the episode includes both unguarded honesty and affection for creative weirdness. It’s playful (“knock, knock, who’s it for?” becomes a motif for both horror and pure improv). Beneath the bits are real insights into performance anxiety, managing creative egos, the meaning of horror, and the belief that weirdness is a universal, not-so-secret superpower.

For New Listeners

This episode distills the essence of "You Made It Weird": blending improv, vulnerability, show business wisdom, and joyous weirdness. Even if you’re not a horror buff or an industry insider, you’ll leave it with a new appreciation for creatives who carry “secret weirdness” — and the catharsis of facing your monsters, onscreen and off.