Podcast Summary: All Of It with Alison Stewart

Episode: Jeff Hiller's Book 'Actress of a Certain Age'
Date: December 29, 2025
Host: Alison Stewart (A)
Guest: Jeff Hiller (B)

Overview

This episode centers on Jeff Hiller’s memoir, Actress of a Certain Age: My 20-Year Trail to Overnight Success. Known for his role as Joel on HBO’s Somebody Somewhere, Hiller shares candid, humorous, and touching insights from his life and career as a “not-quite-famous” actor. The conversation explores Hiller's approach to memoir writing, his personal journey—including struggles, late-blooming success, grief, and coming out—and the realities of working in the arts. The episode masterfully blends comedic moments with deep personal reflection, giving listeners an honest look at resilience, hope, and authenticity.

Key Discussion Points & Insights

Why Celebrity Memoirs? (01:34)

• Love for Memoirs: Jeff discusses his obsession with celebrity memoirs, noting their entertainment value, especially when celebrities mention knowing each other pre-fame.

  “When they're famous, it's even more fun. Cause you know, they usually know other famous people and talk about them.” (B, 01:36)

• Seeking Hope: Jeff admits his deeper motivation was aspirational, reading memoirs for hope that he might one day become successful enough to write one himself. (01:47)

What Hiller Avoided in His Memoir (02:01)

• Common Memoir Pitfalls: He avoids overdone tropes, like elaborate family histories or the “bait-and-switch” surprise reveals.

  “I didn't want to talk about my grandparents. Nobody cares about your grandparents.” (B, 02:09)

• Authenticity and Humor: Hiller shaped his memoir to be “authentic and funny,” eschewing cliché for honesty—sprinkled with a lot of jokes. (02:52)

Writing Process and Format (03:05)

• Incorporation of Solo Shows: The book is “Frankensteined” together from solo shows Hiller performed, giving him material already tested before audiences.

  “At least if you have the same ears as a lot of people at Joe's Pub, I think you'll like it.” (B, 03:24)

• Unique Chapter Headers: Each chapter starts with a celebrity memoir title and an asterisk with factual info about when that celebrity got their “break.”

  “I would find out when they got their big break... and compare it to my age, and it was always a disappointment.” (B, 03:51)

Lessons on Comparison and Hope (03:51)

• Hiller shares the futility and despair of chronically comparing oneself to others’ timelines.

  “Everybody's story is unique and special, and if you're comparing yourself all the time, you're gonna be despairing.” (B, 03:57)

• Encourages embracing individuality and patience—even if fame is late to arrive.

  “…this old queen didn't get a break until 45 years old.” (B, 04:23)

Rock Bottom and Resilience (04:30–05:48)

• “Cookie Rock Bottom”: Jeff recounts a low point after his mother’s passing, describing “numbing himself with baked goods” as a form of unhealthy coping.

  • Memorable moment: His detailed ode to different types of Tate’s cookies.

  “The point is, I had turned 40, my mom... had just died, and I was feeling like... I am teaching improv and temping and I want to be an actor and I'm not.” (B, 05:04)

• Realization: Even during that moment, he knew food wouldn’t “fix” things but ultimately it prompted a journey toward gratitude and self-acceptance.

Influence of Self-Help Books & Vulnerability (06:16–07:35)

• Favorites: Pema Chödrön, Brené Brown (“You need to be vulnerable”), Eckhart Tolle.

  “...that's sort of how I've lived my whole life.” (B, 06:54)

• Owning Mistakes: Hiller discusses a typo on his book cover—“Actress of a Satane Age”—and how owning the error publicly fostered connection and acceptance online.

  “Rather than deny it... I'm just owning it.” (B, 07:10)

  • The typo inspired others to share their own “typo stories,” creating a community of shared vulnerability.

Growing Up and Coming Out (08:21–09:34)

• Texas Childhood: Growing up gay in 1980s Texas was difficult; strong support from his mom made a difference.

  “A wonderful place for a profoundly homosexual child to develop.” (B, 08:29)

• Mother’s Acceptance: His mom proactively prepared for his coming out, showing love and readiness.

  “She just wanted to know more just in case this issue ever came up.” (A, 08:54)
  “She said, I know.” (B, 09:20)

• Father’s Quiet Support: His father, though less verbal, demonstrated acceptance through consistent care.

• Peer Acceptance: Humorously shares an anecdote about coming out to another gay man—a waiter—whose response:

  “Yeah, girl, no duh.” (C, 10:06)

“Acting Straight” and Social Observation (10:33–11:21)

• Jeff reflects on his attempts to “act straight” and how unconvincing they were, as well as offering pointed (and funny) advice to women about men.

  “If you have that question, he isn't. Go run away, find a nice guy that you think is a little bit boring, and marry him.” (B, 11:09)

Struggles of Making It in NYC (11:26–13:49)

• Early Apartments: Describes housing struggles, vividly recounting the fierce competition for affordable apartments.

  “Over 200 people showed up for a 250 square foot studio apartment with no closet.” (B, 11:53)

• Harlem Beginnings: First apartment in Harlem, marked by moments of naivete and the changing landscape of gentrification.

• Classic NYC Experience: Waiting in line at 3 a.m. for Shakespeare in the Park—amidst wild dogs, muggings, and ultimately, seeing Meryl Streep.

  “We just barely got in to see Meryl Streep and Kevin Klein in the Seagull in Shakespeare in the Park. Even though that was Chekhov.” (B, 13:31)

• Despite the chaos, these experiences made Jeff more determined to stay in New York.

The Actor’s Reality: Auditions & Rejections (14:03–15:06)

• Recalls a notorious audition room at Roundabout Theater Company—with the bathroom inside the rehearsal space.

  “I had to ask Oscar winning director Sam Mendes if I could go to the bathroom in the middle of my audition...” (B, 14:28)

• Humorous yet cringe-inducing tale about being overheard by Sam Mendes.

  “Happy Pride. WNYC.” (B, 14:45)

Advice for Aspiring Actors & Artists (15:06–16:31)

• Perform for the Joy, Not the Agent:

  "...Don't worry about the agent. The agent will come. Worry about the performing..." (C quoting B, 15:07)

• Longevity & Process Over Hits:

  “A career is built on longevity, not on making the top 30 comics under 30 lists... There isn't an expiration date on performance.” (C quoting B, 15:16)

• Enjoying the Journey: Jeff encourages finding joy in auditions and reminds creatives that you don't need permission, credentials, or gatekeepers to make art.

Breakthrough and Meaning in Success (17:04–17:44)

• Defining the “Big Break”:

  “Somebody Somewhere, without a doubt. It's the first time I've been able to not have to temp or teach improv... and people... connected to it and love it.” (B, 17:14)

• Audience Connection as Fulfillment: Being stopped by appreciative fans brings pride and meaning.

Starstruck and Staying Humble (17:44–18:21)

• A star encounter—meeting Jonathan Groff—was tempered by Hiller spilling mustard down his shirt, keeping things humble (and hilarious).

Notable Quotes & Memorable Moments

• On Comparison:

  “If you're comparing yourself all the time, you're gonna be despairing, and you start to lose hope and become a little cynical. And I don't want to live a life like that.” (B, 03:57)

• On Owning Mistakes:

  “You just have to own it. And, you know, what are you gonna do? I can't change it at this point... So rather than, you know, having an environmental disaster where we repulp books, we're just gonna somehow be okay with it.” (B, 07:58)

• On Making Art Without Permission:

  “If you want to paint, you can paint. If you want to perform, all you need is, you know, the mirror.” (B, 16:31)

• On Artistic Longevity:

  “A career is built on longevity... There isn't an expiration date on performance.” (C quoting B, 15:16)

Timestamps for Key Segments

• 01:34 – Why Jeff loves celebrity memoirs
• 02:01 – What he avoided in his memoir
• 03:05 – Book format and process
• 04:30 – Midlife crisis "cookie rock bottom"
• 06:16 – Self-help books & vulnerability
• 08:21 – Growing up and coming out
• 11:26 – Struggling to live in NYC
• 13:43 – Shakespeare in the Park adventure
• 14:03 – Audition anxiety & Sam Mendes story
• 15:06 – Career advice for actors
• 17:04 – Defining the “big break”
• 17:44 – Meeting Jonathan Groff

Tone & Style

The episode mirrors Hiller’s wit and warmth—his stories are filled with self-deprecating humor, honesty, and empathy. Serious themes are approached with levity and hope, leaving listeners both entertained and inspired.

This summary captures the spirit, stories, and advice offered by Jeff Hiller—providing a detailed, timestamped roadmap for anyone looking to understand his path and perspective without having listened to the full episode.