Craig Bierko: The Last Will and Testament of an Extremely Distinguished Dog

Wed Sep 17 2025

Craig Bierko (Boston Legal, UnREAL) joins Woo Woo to talk about the love of his dog Boo, and how a well-timed gift helped him at a difficult time. Plus a visit to a channeler introduces him to the spirit of Zosh! Who’s Zosh, you ask? Listen in to hear an impression of Zosh as well as Richard Kind!

Transcript

A (0:00)

This episode is brought to you by Progressive Insurance. Fiscally responsible financial geniuses, monetary magicians. These are things that people say about drivers who switch their car insurance to Progressive and save hundreds. Visit progressive.com to see what you can save. Progressive Casualty Insurance Company and affiliates. Potential savings will vary. Not available in all states or situations.

B (0:24)

Your teen adjective used to describe an individual whose spirit is unyielding, unconstrained. One who navigates life on their own terms, effortlessly. They do not always show up on time, but when they arrive, you notice an individual confident in their contradictions. They know the rules, but behave as if they do not exist. The new fragrance by Miu Miu, defined by you. Welcome to Woo Woo with Rachel Dratch, the podcast that explores the unexplained with humor and curiosity. Hello and welcome to Woo Woo with Rachel Dratch, here with friend and beloved co host, Irene Bremis. Hi, Irene.

C (1:19)

Hello, sweetie.

B (1:21)

Irene, we are in person coming to you from the esteemed Players Club. Today this guy said he wanted to meet in person and we said, sure. Please welcome. He trekked it on down from the Upper west side. Please welcome actor man about town and New Yorker extraordinaire, Craig Bierko.

A (1:42)

Extraordinaire. Hello. I'm happy to be here. Do you resent being here?

B (1:47)

No.

A (1:48)

If you guys want to go home, I'll solo this.

C (1:51)

I love you.

B (1:51)

No, I said that because it's a special event. It's like a special event presentation.

A (1:55)

I just thought it's always better to be in the room. And then the first episode I listened to was Will fetch Daryl, who's like calling in from an igloo.

B (2:01)

Like, you know, that was back before we had refined our technical. We had a lot of technical difficulties. Poor Will had to sit through.

C (2:08)

He had to sit through those. Yeah, that was hard for him.

B (2:11)

We changed our system anyway, but here we are. This is the old fashioned system.

Summary

Podcast Summary: Woo Woo with Rachel Dratch – “Craig Bierko: The Last Will and Testament of an Extremely Distinguished Dog”

Host: Rachel Dratch
Co-host: Irene Bremis
Guest: Craig Bierko
Date: September 17, 2025

Episode Overview

In this heartfelt and humorous episode, Rachel Dratch and Irene Bremis welcome actor and Broadway star Craig Bierko to explore questions of loss, connection, and the uncanny moments that make life feel “woo woo.” Craig shares personal stories about his late dog Boo, synchronicities that comforted him during grief, and unexpected spiritual experiences, blending honest emotion with comedic wit. The conversation meanders through stories about Broadway, celebrity encounters, grief rituals, channelers, past lives, and the healing journey of pet ownership—showcasing how laughter and the unexplainable go hand in hand.

Key Discussion Points & Insights

1. Craig’s Broadway Past & Rachel’s Fangirling

Rachel opens with admiration for Craig’s Tony-nominated role in The Music Man (02:20).
Craig does an impromptu patter of “Ya Got Trouble” from The Music Man (03:01).
Nostalgic banter about memories from Celebrity Autobiography and meeting Rosie O’Donnell, including offhand showbiz advice (“You can’t be heavy. I can be heavy, you can’t be heavy.” —Rosie, 06:55).

2. Grief, Love, and the Woo Woo of Dogs

Craig recounts the deep loss of his dog Boo post-pandemic, describing the transformative love and the pain of letting go (08:12).
He shares a vivid “woo woo” moment: At the peak of his grief, a distant acquaintance, Peter Chatsky, sent him Eugene O’Neill’s Last Will and Testament of an Incredible Dog, which arrived at the exact moment he was about to break down in tears (10:11).

“It was the will written by the dog… the only thing I can leave you is that raincoat… It would be a shame if the love we had didn’t transfer onto another dog.” – Craig, paraphrasing Eugene O’Neill (12:09)
Craig describes lingering moments with Boo’s presence (“I’d get up to use the bathroom and say ‘I’ll be right back’—but there’s nobody there, no dog.”) (14:05)
Minutes before the episode, he met a woman at an Apple Store with a dog, who worked for a foster organization—another synchronistic moment encouraging him to adopt again (15:41).

“That literally happened. That happened an hour ago.” – Craig (15:45)
Reflection on how caring for Boo made Craig “the best [he] had ever been as a person” (21:09).

3. Audience Connection & Pet Adoption

Hopeful shout-out to listeners grieving pets, wishing them healing and encouraging future adoptions (23:31).

“My wish is that this podcast leads them to that when they're ready for it.” – Craig (23:31)

4. Craig’s Brush with the Mystical: Channelers in Sedona

Craig describes visiting Sedona and meeting renowned channeler Robert Shapiro, who enters a trance and channels “Zosh” (28:10).
In the reading, Craig is told he was a “fisherman poet” in ancient Greece: “You used to get up in the bistros and read your poetry to the other fishermen…and as you got older you would read your poems to the fishes.” (30:13)

“Karma is like a big record album… if you don’t solve something in one life, it’s going to come around again in the next.” – Craig via “Zosh” (31:18)
Years later, while filming in Malta, Craig has a profound “past-life” moment: looking out over the Mediterranean, he sees a lone fisherman in a boat, and it feels “sacred,” linking to his Sedona experience (33:19).

5. Open-Minded Skepticism & Creative Discipline

Conversation about the balance between healthy skepticism and openness to the mystical, especially in moments of creative or personal need (24:33, 39:32).
Reflections on writing, discipline, and how pain is necessary for creative output (writing “is how much pain you can take.” —31:38).

6. The Pendulum Segment: Seeking Guidance

The group engages in a “pendulum” ritual, using it to ask yes/no questions—mostly about future dogs, and Rachel’s career awards (40:09).
Light teasing about showbiz anxieties and dreams—Rachel jokes about the pendulum denying her Tony dreams (40:45).

7. Mutual Support and Comic Relief

Craig expresses deep gratitude for the joy and solace he finds in comedy, especially Rachel’s iconic “Debbie Downer” sketch.

“It is something. That’s one of those go-to little pills you can take to make you feel better.” – Craig (43:41)
Rachel shares that filming “Debbie Downer” was as fun in real life as it looked, despite “trying so hard not to laugh.” (43:19)

8. Woo Woo Zodiac: Nailing Craig’s Sign

In a rare moment of triumph, Rachel and Irene both correctly guess Craig’s zodiac sign—Leo—eliciting laughter and surprise (44:05).

Notable Quotes & Memorable Moments

On spiritual openness:

“I wasn’t sure how woo woo I was. I’m very open to… We don’t know what’s going on.” – Craig (08:12)
On grief and comfort:

“It was exactly, perfectly timed. The cry did come… It was the last big cry, but it was… for the crying section, for the raw emotion.” – Craig (14:05)
On synchronicity:

“That literally happened. That happened an hour ago.” – Craig, after describing a woman encouraging him to adopt a dog, as he headed to the podcast (15:45)
On life with his dog Boo:

“I was the best that I had ever been as a person… when I had to, you know, there’s no giving in because you feel sad or depressed… you gotta take the dog out…” – Craig (21:09)
On past lives & karma:

“Karma is like a big record album… if you don’t solve something in one life, it’s going to come around again in the next life.” – “Zosh” via Craig’s channeling experience (31:18)
On writing:

“Any writer who tells you it’s anything other than how much pain you can take, they’re lying to you.” – Wisdom relayed by Craig (31:38)
On “Debbie Downer:”

“That is such a joyous moment… one of those go-to little pills you can take to feel better.” – Craig (43:40)

Timestamps for Important Segments

[02:20] Rachel discusses Craig’s role in The Music Man
[03:01] Craig performs “Ya Got Trouble” patter
[06:55] Showbiz advice from Rosie O’Donnell
[08:12] Craig’s woo woo openness and the story of losing his dog Boo
[10:11] The “Last Will and Testament of an Incredible Dog” arrives at a pivotal moment
[14:05] Describing the timing and emotional impact of receiving the book
[15:41] Fresh synchronistic event: Apple Store, dog foster woman
[21:09] How caring for Boo made Craig a better person
[23:31] Wishing healing for other grieving pet owners
[28:10] Sedona, channeler Robert Shapiro, and meeting “Zosh”
[30:13] Fisherman poet past life reading
[31:18] Karma and unfinished lessons in life
[33:19] Malta moment: seeing the fisherman, resonance with past life
[39:32] Rachel and Irene discuss skepticism and openness in psychic encounters
[40:09] Pendulum section: asking about future dogs and Tony awards
[43:19] Behind the scenes of “Debbie Downer”
[44:05] Both correctly guess Craig’s zodiac sign as Leo

Episode Tone and Vibe

The episode is a signature blend of humor, warmth, and vulnerability—true to the Woo Woo brand of “curiosity with comedy.” Craig’s emotional honesty is met with empathy and playful irreverence from Rachel and Irene. The storytelling is both poignant and absurd; synchronicity, psychic readings, and the mysteries of loss and creativity are treated with open-minded skepticism and genuine wonder. The episode ends on a buoyant note, reflecting the healing power of laughter, friendship, and, of course, dogs.

For Listeners

If you’ve ever grieved a pet, wrestled with creative blocks, or just wondered whether that meaningful coincidence was “woo woo,” this episode is for you. You’ll laugh, maybe cry a bit, and definitely feel less alone in those blurry spaces between the explainable and the magical.

Follow the hosts:

Rachel Dratch: @raedratch
Irene Bremis: @irenebremis

Woo Woo with Rachel Dratch is brought to you by QCODE.