You Made It Weird with Pete Holmes

Episode: The Sklar Brothers Return (March 12, 2025)

Episode Overview

Comedians Randy and Jason Sklar return to Pete Holmes’s podcast for a characteristically freewheeling, laugh-soaked conversation about the weirdness of comedy, generosity in their craft, memorable industry stories, religious upbringing, and growing older as artists and friends. The episode is a rollicking blend of sharp bits, affectionate roasts, inside comedy baseball, and surprisingly earnest discussions about meaning, spirituality, legacy, and “the soul of comedy.” Fans of improvisational riffing and philosophical tangents will find a goldmine, with all three hosts at their quickest and most authentic.

Key Discussion Points & Insights

1. British “Randy,” Language, and “Sounding”

• [02:01] The Sklars share a running joke invented by Kumail Nanjiani where “Randy” (in the British sense, i.e., feeling sexy) becomes a podcast bit.
• [02:59] Spirals quickly into riffing about language differences and “sounding” (a sexual practice)—leading to a punchline about Seattle’s soccer team being named “Sounders” and how sometimes names mean more than intended.

“Tell me you like urethra play without telling me you like urethra play.”
— Jason Sklar [03:35]

2. Comedy Scenes, Tagging, and Generosity

• [11:09] Pete praises the Sklars for their generosity: “Saint Sklars of the comedy scene,” especially via their “Tag It” show, where comics punch up each other’s sets with tags and additions.
• The Sklars reflect on shifting from “just hustling” to creating an inclusive, supportive comedy environment.
• [14:10] Jason emphasizes that laughing at another comic’s joke is a form of generosity, and “tagging” is both an honor and creative trust.
• [15:16] Discussion about potential for a more formal “Tag It”–style TV show or summer camp.

“Can we create a world that we would want to live in in comedy?”
— Randy Sklar [11:59]

3. The Alchemy of Jokes: Process & Philosophy

• [19:31] Pete walks through his creative process with an “eye patch joke,” illustrating how riffing with the Sklars in his head leads to unfolding more layers of a bit.
• Discussion on maximizing a premise (“taking every piece of meat off the bone”) and not jumping off before you land every punchline.

“Why did you bring it up if you’re just gonna be like—”
— Jason Sklar, on exploring every comedic premise [21:43]

• [22:43] Citing Stephen Wright and others, comparing jokes to “painting little paintings” in the mind, and likening well-done material to a parachute opening at the right moment.

“Jokes are like painting little paintings in people’s minds.”
— Stephen Wright, relayed by Pete Holmes [22:43]

4. Comedy Styles: Relief, Gatling Guns, and Edging

• [24:01] Contrasts different comics’ timing and delivery, e.g. Steven Wright, Nate Bargatze, and Anthony Jeselnik—discussing suspense, “relief” at punchlines, and “edging” (comedic and otherwise).
• The Sklars and Pete celebrate both rapid-fire and high-suspense styles.

5. The Depths: Meaning, God, Soul, and Legacy

• [32:09] Pete shares his journey on writing deeper (“meaning of life”) material and how seeing other comics’ fearlessness, like Billy Wayne Davis, inspired him to distill big ideas into accessible bits.
• The “God or nothing” bit becomes a point of connective pride for Pete—eliciting positive feedback from believers and non-believers alike.

“God is the name of the blanket we put over the mystery to give it a shape.”
— Pete Holmes [32:22]

• Sklars discuss finding common ground religiously despite doctrinal differences, and how community, questions, and celebration transcend rigid dogma.

6. Heritage & Culture: Judaism, High Holidays, and Family Rituals

• [64:06] The Sklars reflect on Jewish summer camp, Passover seders, sharing family “dad” jokes, and making fun of both the rituals and themselves. They riff on “sexual” sounding Passover phrases and how family comedy traditions shape character.

“The 11th Plague would be a hilarious name for a Jewish comedy club.”
— Randy Sklar [66:14]

7. Comedy Community: Growth, Failure, and Generosity

• [41:00] Sklars and Pete discuss humility, growth, aging, comedy as a spiritual path, and learning more by admitting what you don’t know.
• [41:50] The real spiritual “success” is spaciousness, gentle unknowing, and journeying together rather than fierce certainty.
• [43:34] Judaism’s tradition of asking “why”—and how that naturally dovetails with stand-up’s relentless questioning.
• [90:00] Their ever-renewed commitment to being forces for generosity and support for other comics.

“Can we leave the comedy community as: let’s love each other, let's give to each other, let's make each other’s comedy better?”
— Randy Sklar [90:34]

8. Industry Stories, Roasting, and Showbiz Inside Baseball

• [81:32] Extended detour about roast battles at Montreal’s Just for Laughs (with Jimmy Carr, Finn Taylor, Brad Williams, Blake Griffin) and the insane adrenaline of competitive joke writing.
• Vivid anecdotes about bombing, killing too hard in a roast, and punching up delicate material.

“You get a writer’s room laugh, which is the thing that’s making us laugh. We gotta scrap all the other things.”
— Jason Sklar [86:13]

9. Philosophy of Relationships, Teams, and Generous Interpretation

• [76:00] The brothers liken partnership to marriage: sometimes things aren’t even, but the larger goal is more important than small grievances.
• Discussion of the virtue and comfort of “benefit of the doubt” as a love language, and the beauty of “unoffendable” friends.

“Giving me the benefit of the doubt is my love language.”
— Pete Holmes [76:11]

• [77:04] Reference to Richard Rohr and Ram Dass: true spiritual maturity means being "unoffendable" and not excluding anyone from your heart.

Notable Quotes & Memorable Moments

• “Takes two to know one.”—Running meta-gag about podcast titles and group dynamics. [09:51]
• “Tell me you like urethra play without telling me you like urethra play.”—Jason riffs on sexual subculture jokes. [03:35]
• “When you laugh at another comedian's joke, that is generosity.”—Randy on solidarity in the scene. [14:10]
• “God is the name of the blanket we put over the mystery to give it a shape.”—Pete's core bit on spirituality. [32:22]
• “It’s not the gain. It’s that it’s gaining.”—On inherited immigrant thrift and both career and spiritual growth. [39:23, 93:48]
• “Comedy cancer”—Pete’s label for haters and why hanging with positive peers matters. [40:14]
• “My favorite people are the Unoffendables.”—Pete on his inner circle. [76:33]
• “Dondas as Donas is a great bonus.”—Wherein they merge Trump and Ram Dass. [93:29]
• Rapid-fire bit: Jewish jokes about bar mitzvahs, family seders, and “extra chairs from the basement.” [67:29]
• “You guys get recognized more because you get a second chance. You have two faces.”—Pete roasts the Sklar twins. [78:35]
• “He had Sklar brother–level of fame. People would be like ‘where do I know you from?’”—Comparing Jesus’ contemporary notoriety to theirs. [79:34]

Important Segment Timestamps

• [02:01–04:40]: “Randy” jokes, “Sounding”, and soccer team names.
• [11:09–14:43]: Saint Sklars, Tag It, comedy community philosophy.
• [19:31–22:26]: Pete’s creative mechanics with joke riffing and “taking it all the way.”
• [24:00–26:40]: Comedy as “edging,” joke timing, and punchline suspense.
• [32:09–36:00]: Writing big bits about God, fearless comedy, and religious differences.
• [41:00–44:16]: Comedy as asking “why”—Judaism parallels.
• [64:06–69:11]: Sklars’ Jewish upbringing—family jokes, Passover, sexualized ritual phrases.
• [81:32–88:21]: Behind-the-scenes of roast battles, anxiety, and the adrenaline of live comedy combat.
• [76:00–77:39]: Partnership, benefit of the doubt, “unoffendable” friends.
• [90:00–91:00]: The Sklars’ comedy legacy: generosity and love for the community.
• [92:44–93:29]: Trump meets Ram Dass impression.

Tone & Style

The tone is wild, improvisational, joyous, and affectionate, punctuated with sudden turns toward sincerity and deep reflection. The episode is a love letter to comedy and comedians, peppered with industry in-jokes and plenty of infectious laughter. The Sklars and Pete continually subvert bits with unexpected philosophical depth, creating a signature style: part riff, part group therapy, part roast, and always weird.

Best For

• Fans of standup comedy and inside-industry chatter.
• Anyone interested in the creative process and philosophy of joke-writing.
• Listeners craving both laughter and honest talk about meaning, friendship, and growing older in creative life.
• Comedy nerds who love meta-humor, callbacks, and affectionate roasts.

Final Note:
This episode is a gem for fans of smart, silly, and sincere comedy. The Sklars and Pete Holmes set a standard for creative generosity and mutual admiration, offering aspiring comics a playful but profound roadmap to community and craft.