Staying Alive with Jon Gabrus & Adam Pally

BONUS: An Intimate Evening With Adam Pally!

Date: October 20, 2025
Network: SmartLess Media

Episode Overview

This special bonus episode takes a deep dive into Adam Pally’s creative process in developing his latest HBO comedy special. Hosted by best friends and comedians Jon Gabrus and Adam Pally, the episode offers honest, funny, and revealing reflections on imposter syndrome, the evolving nature of comedy, and the journey from live bits to a fully-realized televised special. The conversation radiates friendship, encouragement, and the desire for self-improvement—hallmarks of the Staying Alive podcast.

Key Discussion Points & Insights

1. The Making of an HBO Special

• Adam and Jon reminisce about the journey from the early days of performing live bits to landing an HBO comedy special.

• Adam describes the organic, incremental development of his show: what started as small segments at clubs like Largo evolved, bit by bit, into a cohesive hour-long performance.

  “You just started doing it. It was just like, ‘I think I should start doing a one man show.’ And so that starts with like a bit here and then a bit there… then your five minute chunks pieced together… and then you’re like, wow, I have something here.”
  — Adam Pally (02:03)

• Jon expresses his pride and excitement for Adam, highlighting the rarity and magnitude of landing a special on HBO.

  “You have an HBO in HBO comedy.”
  — Jon Gabrus (02:52)

• Adam opens up about moments of imposter syndrome and the dream-come-true feeling of seeing his name on billboards—accidentally catching it, rather than deliberately seeking it, makes it even sweeter.

  • Memorable moment: Adam seeing his face on a Beverly Center billboard (01:22–01:46).

2. Creativity, Style, and Self-Esteem

• Adam reflects on his comedic style—less about observational “of-the-moment” humor, more inward-looking, drawing on his life experience, musical talent, and unique perspective.

• The conversation touches on the challenge of self-doubt and feeling “not as funny as everyone else”—and how this project challenged and changed that self-perception.

  “Oftentimes I struggle in the idea of like, why, why would—what’s special about me?... I have imposter syndrome, as we all do.”
  — Adam Pally (02:59)

• Jon provides heartfelt reassurance and points to Adam’s multidimensionality in performance as his unique gift.

  “You’re doing stuff that not everyone can do… you’re synthesizing all that into a show.”
  — Jon Gabrus (03:22)

• Adam recognizes a pattern in his life of “just getting by,” relating to broader issues of unfulfilled potential and the need for self-compassion.

  “I think what doing this showed me is that…I need to be kinder to myself on that, because…I work a lot harder and I think I’m better.”
  — Adam Pally (05:35)

• The pair laugh about Adam’s feelings of perpetual “not-quite-thereness”—including the all-too-relatable “15 pounds overweight” remark.

  “I’m 15 pounds overweight. If I could just lose those 15 pounds…”
  — Adam Pally (05:24)

3. Non-Traditional Comedy and Musical Interludes

• Adam discusses the hurdles of developing a show that isn’t “straight stand-up”—using music and more complex bits.

  “There’ll be people who’ll be like, ‘this isn’t technically stand up comedy.’ And you’ll have to just be like, okay, fine.”
  — Jon Gabrus (07:42)

• He shares a revealing anecdote about easing live audiences into his musical material by telling a half-true story about working on a musical.

  “I used to have to come out and make up this lie, which was like… I’m working on a musical. And some of it has cover songs, some of it has originals… what it did was it let the audience go, ‘well, at least he’s not a comic with a guitar.’”
  — Adam Pally (07:58)

• Memorable moment: Adam playing “Piano Man” in full on guitar, with the audience waiting for a punchline that never comes—demonstrating his love of playing with comedy forms and expectations.

  “I would play the entire song of Piano Man on guitar…with no punchline. The whole thing is the punchline.”
  — Adam Pally (09:00, 09:07)

• Quick, lighthearted digression about how “Piano Man” should technically be called “Harmonica Man.”
  — (09:14–09:35)

4. Release, Anticipation, and Celebration

• Adam’s special is now live on HBO Max, and Jon jokes about it already being bootlegged.

  “It’s being bootlegged… you can buy it from the nail technician at your pedicure store.”
  — Jon Gabrus (09:59)

• Adam hopes fans approach the special with an open mind—if they like his previous work, it will deliver.

  “View it the way you view a lot of my stuff. I don’t think you need to expect anything different. It’ll deliver. If you, like me, it'll deliver.”
  — Adam Pally (10:28)

• They discuss the music’s added value: it’s good enough for a second, “background” listen.

  “You can put it on and cook dinner. Cause the music is kind of good, you know… I think it’s got a lot of functions.”
  — Adam Pally (10:46)

• Adam shares plans for the special’s premiere party—complete with a tongue-in-cheek red carpet interview segment.

  “Cole wants to stand with a microphone and interview everyone that comes through about their outfit.”
  — Adam Pally (11:19)

Notable Quotes & Memorable Moments

• On imposter syndrome and authenticity:

  “The nicest compliment you gave me… it is you.”
  — Adam Pally (04:14)

• On self-doubt and potential:

  “I think I have more. I think I have another gear, a couple more gears I think I can go to.”
  — Adam Pally (05:02)

• On creative risk:

  “The whole thing is the punchline.”
  — Adam Pally (09:07)

• On audience expectations:

  “There’ll be people who’ll be like, ‘this isn’t technically stand up comedy.’ And you’ll have to just be like, okay, fine.”
  — Jon Gabrus (07:42)

• On celebration and camaraderie:

  “Can’t wait for America to know what I already know about you.”
  — Jon Gabrus (10:57)

Recommended Listening Timestamps

• 01:22–01:46
  Billboard surprise—Adam reflects on casually seeing his face on a Beverly Center ad.
• 02:03–03:13
  The organic process of developing the show and Adam’s reflections on imposter syndrome.
• 05:02–06:30
  Discussion around self-perception and recognizing untapped potential.
• 07:42–09:07
  Comedic style and audience expectations, with the “Piano Man” musical bit story.
• 10:28–11:03
  Advice for watching the special and hopes for audience reception.
• 11:08–11:30
  Premiere party anticipation and red carpet bit.

Tone

The episode is loose, candid, hilarious, and heartfelt—full of gentle ribbing, inside jokes, and honest talk about creativity and self-worth. Both Adam and Jon maintain their trademark self-deprecation and affectionate banter, resulting in an intimate celebration of creative risk and friendship.

For anyone interested in the intersection of comedy, music, and the creative process—as well as those grappling with the ever-present imposter syndrome—this episode provides both laughs and genuine inspiration.