You Made It Weird with Pete Holmes

Guest: Jason Sudeikis (Re-Release)

Date: July 16, 2025 (originally 2018)
Description: Pete Holmes and Jason Sudeikis (SNL, Horrible Bosses, Ted Lasso) dive into the weirdness of comedy origins, improv, humility, process, and the search for meaning—with plenty of anecdotes and laughs.

Episode Overview

Pete Holmes sits down with Jason Sudeikis in this energetic, generous, and winding episode, originally recorded before Sudeikis became globally recognized as Ted Lasso. The conversation moves freely between comedy process, improvisational wisdom, humility in the arts, the metaphysics of group creation, personal and family histories, mentorship, mushrooms, magic, and the perpetual weirdness at the heart of being a comedian.

Key Discussion Points and Insights

The Comedy Path & Early Influences [03:37–19:10]

• Comedy Incubation: Kansas City and Chicago

  • Sudeikis recalls his formative years doing short-form improv at ComedySportz, Kansas City, where he performed 500+ shows before moving to Chicago (14:05).
  • The importance of “trying on” voices and comedic influences (Sandler, Farley, Chevy Chase, Aykroyd) as a necessary phase for finding your comedic individuality:
    • “Every funny person you know was doing somebody else”—Pete (16:28)
    • “That's why you do the reps. You want to put it in the blender.”—Jason (17:09)

• Moving from Mimicry to Authenticity

  • Discussing the process of outgrowing direct imitation and fusing influences into one’s own style.
  • The value of humility and being "the dumbest person in the room" to learn from others (18:47):
    • "One of my favorite things I like to be is try to be like the dumbest person in the room, you know, and then just learn from these men and women."—Jason (18:47)

Improv Wisdom and Lessons [44:00–66:46, 170:08+]

• Lessons from Chicago's Improv Scene

  • Jason’s formative experiences at Improv Olympic and Second City:
    • He was recognized early by teachers and peers for his listening skills and scene work (48:49), reciting his now-famous dart scene from his Second City audition (58:13).
    • The importance of “big ears”—listening in improv, as emphasized by Del Close and Mick Napier.
    • “Listen, have, like, Del said, like, the jazz drummer. Have big ears.”—Jason (171:39)
  • Learning to “love the art in yourself versus yourself in the art” (66:03), insisting on process and selfless collaboration.

• Process vs. Product and Ego

  • The tension between improv as creation vs. end result, and dealing with the “anxiety of influence” as new levels of accomplishment are reached (29:20).
  • “It’s more important to love the art in yourself than yourself in the art.”—(66:03)

Comedy, Music, and Artistic Confidence [06:04–43:46]

• Comedy vs. Music:
  • Pete discusses his ambivalence toward music and why improvisers often feel they could do any creative thing after seeing it done.
  • Sudeikis confesses similar feelings after watching dance prodigy Savion Glover—he bought tap shoes and realized true genius is rare (12:50).
    • “I was like, oh, I could do that. I bought tap shoes...I wore them once. I was like, I can’t do what that son of a gun’s doing.” —Jason (12:31)
• Self-Doubt and Healing:
  • Pete reflects on using comedy as a way to heal from feeling dumb or left out as a kid (41:33).
  • They discuss the role of "small dick days" and fluctuating self-esteem (41:05).

Creative Mentorship, Family, and Influence [94:00–124:37]

• Mentors and Heroes
  • Sudeikis credits influential teachers and peers (Tina Fey, Mick Napier, Peter Gwynn, Rich Talarico), sharing their sage advice:
    • “If you can improvise, you can write.”—Tina Fey (96:04)
    • “Don’t write something for someone that you can do yourself.”—Tina Fey (96:04)
  • On artistic heroes: Pete describes “obsessions” with figures like Rich Talarico and the nature of borrowing lines/essence from others (99:23).
• Family as Support and Inspiration
  • Sudeikis describes his father's influence, their Lithuanian roots, and the peculiar “Sudeikis” family arc (133:13).
  • "Love [people] for who they are and where they're at, not where you think they should be."—Jason (174:43)

Themes of Joy, Process & Soul Points [33:07, 67:08+]

• The Magic Beans
  • They explore the idea of everyone starting their journey with unique “magic beans”—the joyful, innocent skills that later become signature moves (33:07).
    • Sudeikis on his iconic SNL dancing: “Here I go ... the thing I’m geeky about...yet everybody’s just like, no, man, that dancing, that joy you have when you dance is the same joy I had when I was 13.”
• Soul Points and Purpose
  • Parallels to Mark Duplass’ “soul points”: creative energies, where and how to spend them as one matures as an artist.

Coping with Insecurity & The Need for Validation [106:44–112:57]

• Navigating Doubt
  • Both share candid moments about confidence and imposter syndrome, even after major success.
    • “Here I was ... maybe I’m fundamentally a cursed person. Like, what are you doing?”—Pete (107:25)
• Finding Meaning Beyond Accomplishments
  • Sudeikis emphasizes that success is not about the external but about the real connections and present moments with family and creative collaborators (113:40).

Magic, Mushrooms & Mysticism [80:05–153:31]

• Love of Magic:
  • Sudeikis’ passion for magic began in childhood and continues, tying performance to a search for the mysterious in life (80:05).
• Mushrooms and Mystical Experiences
  • The impact of psychedelics on creativity, perception, and group unity—“mushrooms and improv sort of are ...” (141:55), with detailed, funny stories (142:02).
  • “You get to feel like a Marx Brother ... see people’s auras and essence.”—Jason on mushrooms in Vegas (149:39)
• Metaphysics of Collaboration
  • Tie-ins with improv as a spiritual group mind:
    • “A big part of what we get to do is making the invisible visible for people.”—Jason (116:05)
    • Interconnectedness as “God is like the Spurs. Group mind.” (122:04)

Showbiz and Writing Lessons [171:03–179:06]

• On Saying No
  • “A business career is what is made out of what you say no to.”—Bernie Brillstein via Jason (171:15)
• Writing:
  • “All writing is rewriting.”—Judd Apatow via Jason (173:16)
  • The necessity of hiding the hard work and presenting effortless excellence (180:27)
• Improv/Collaboration Lesson
  • The “big ears” of a jazz drummer as the core of both good improv and life (171:39)

Personal Touches, Notable Quotes, and Fun Moments

• On Chevy Chase as a key influence:
  “I just loved Ty Webb. I just loved Ty Webb because I didn’t ever believe that ... the nonchalance, that level of just kind of like ease.” —Jason (24:51)

• Sudeikis on SNL:

  • “You can forget people actually watch the fucking show. Because you’re just on to the next one...” (30:51)
  • On “What Up With That”: “If people come up to me, 75% ... It’s that dancing, that joy you have when you dance.” (31:26–33:07)

• On the origin of magic and creativity:
  “But I do believe there was a fissure that happened in my brain that also allowed me to possibly look for the magic in the world, too.” (86:14)

• Sudeikis’ accidental Lithuanian genealogy TV episode and the story of his grandfather’s mysterious end (139:06–141:20)

• On psychedelic humility:
  “Mushrooms and improv sort of are [similar] ... It was like this gorgeous, you know, experience with that music, ... I'm seeing Kay’s face emoting in the smoke. All these different things as the lightshow went on.” (143:39)

• Funniest Laugh Memory

  • Pete Gross’ pratfall routine outside a college bar, as recounted by Sudeikis:
    “...he gets up and falls down again...he just keeps doing, like, to the point. He does it for like three straight minutes ... and I’m dying laughing because it’s hilarious ... and then campus police pull over to help him.”—Jason (165:17–166:05)

Timestamps for Key Segments

• [03:37] Jason & Pete riff on SNL world, comedy fears
• [14:05] Kansas City improv scene and mimicking influences
• [33:07] “Magic beans”: Early joy and finding your unique angle
• [48:49] Breakout scene at ImprovOlympic
• [58:13] The “dart scene” at Second City audition
• [66:03] “Love the art in yourself more than yourself in the art”
• [96:04] Tina Fey’s mentorship and writing advice
• [106:44] Navigating insecurity even after success
• [116:05] Improv as making the invisible visible
• [122:04] Sudeikis on God as group mind
• [142:02] Mushrooms, magic, and divine tripping
• [171:15] Bernie Brillstein’s “the power of ‘no’”
• [173:16] All writing is rewriting
• [176:43] Greatest lesson about family
• [179:21] “The harder you work, the luckier you get.”
• [182:30] Wrap up and Magic Castle plans

Notable Quotes

“That’s why you do the reps. You want to put it in the blender.”
— Jason Sudeikis [17:09]

“Listen, have, like, Del said, like the jazz drummer. Have big ears.”
— Jason Sudeikis [171:39]

“It’s more important to love the art in yourself versus yourself in the art.”
— Jason Sudeikis via Del Close [66:03]

“Don’t write something for someone that you can do yourself.”
— Tina Fey via Jason Sudeikis [96:04]

“A business career is what is made out of what you say no to.”
— Bernie Brillstein via Jason Sudeikis [171:15]

“The harder you work, the luckier you get.”
— John Wooden via Jason Sudeikis [176:29]

“Love them for who they are and where they’re at, not who you want them to be.”
— Jason Sudeikis [174:43]

Memorable Moments

• Pete and Jason’s ongoing riff about their tap-shoe confidence and “magic beans” (12:50, 33:07)
• The famous Second City audition “dart scene”—truly a masterclass in improv listening (58:13)
• Sudeikis and Holmes bonding over using real people’s names in sketches and how it helps memory (84:05)
• Sudeikis’ mushy, cosmic story about a personalized light show to Jesus Christ Superstar on mushrooms in Amsterdam (143:39)
• Laughter highpoint: Pete Gross’ endless pratfalls in the ice outside the college bar (165:17–166:05)
• The mutual riff about “good-looking for comedy” and “small dick days” (41:05)
• Pete’s fantasy of being picked to perform as a little boy at the theater—childhood comedy dreams full circle (137:12)

Conclusion and Takeaways

The episode is a joyful, sprawling, and deeply honest look into the mindsets, work habits, joys, and anxieties of successful comedians and improvisers. Through playful conversation and stories, Sudeikis and Holmes share hard-won lessons on humility, the value of process, the necessity of listening, and the beauty of being present—whether on stage, in family, or tripping on mushrooms. Listeners are left with encouragement to revel in their weirdness, embrace the joy of the creative journey, and never lose faith in their own unique “magic beans.”

Final words from Sudeikis:

“Oh, please, keep it crispy… Sometimes it just doesn't show up. I don't know… You just gotta trust yourself sometimes, though.” [182:56]

For comedy nerds, improvisers, Sudeikis fans, or anyone fascinated by the mystery of creativity, this is an indispensable listen.