The HoneyDew with Ryan Sickler
Episode 361: Greg Warren – "I Made it Further Than Shane Gillis at West Point"
Date: November 24, 2025
Guest: Greg Warren
Episode Overview
In this episode, comedian Greg Warren sits down with Ryan Sickler to discuss the "lowlights" of his life – from being a state champion wrestler with a clarinet hidden under his arm, to his time at West Point (where he lasted longer than fellow comedian Shane Gillis), battles with food, OCD, grief, and ultimately finding catharsis through storytelling and stand-up. The conversation is honest and funny, often veering into surprising depths about mental health, family, and the lasting lessons of failure and perseverance.
Key Discussion Points & Insights
Growing Up in St. Louis: The Warren Family
- Background & Family (05:12 – 07:03)
- Greg is the oldest of three boys; his youngest brother is 18 years younger, a surprise to teenage Greg.
- His dad was his high school wrestling coach, which shaped much of Greg’s adolescence:
“My dad was a high school wrestling coach. He was my coach.” (06:51 – Greg Warren)
Wrestling: From 5 Years Old to All-American
- Early Wrestling Life (07:44 – 11:09)
- Began wrestling at age 5, thanks to his dad’s guidance.
- Older brothers were more into soccer; Greg became a standout wrestler.
- Won Missouri state championships at 138 and 145 lbs:
“I think I won it at 138 and 145 my senior year.” (11:03 – Greg Warren)
- His high school wasn’t a wrestling powerhouse, so the recognition was muted compared to other schools.
- Wrestling Culture & Rituals (10:27 – 12:32)
- Ryan shares stories of “Vision Quest”-inspired spotlight matches to attract crowds to wrestling.
- Both discuss the insane rituals of cutting weight with trash bags, saunas, and sweat suits.
Music Nerd Meets Mat Monster
- Musician and Athlete Identity (13:20 – 15:15)
- Despite wrestling dominance, Greg also played clarinet and was musically gifted:
“Yeah, I could do, you know, Rhapsody in Blue.” (13:20 – Greg Warren)
- Ryan highlights the rarity:
“Nobody’s ever sat in that seat and said they could crush the clarinet.” (13:40 – Ryan Sickler)
- Despite wrestling dominance, Greg also played clarinet and was musically gifted:
Choices After High School: West Point & Wrestling
- College Recruitment and West Point Arrival (16:12 – 17:40)
- Recruited by Missouri schools and West Point; chose to attend the US Military Academy.
- Lasted a full year (unlike Shane Gillis), but found the intense regiment wasn’t for him:
“I made it a lot farther than Shane did. I went a full year.” (16:52 – Greg Warren)
- Military Life & Equipment Fiascos (17:57 – 19:11)
- Lost a firing pin during a field exercise, leading to a classic military screaming scene:
“They're screaming at me… but I could also spot the fear in his eye because he knew if I lost that, he’d… It’s coming down on him.” (18:19 – Greg Warren)
- Realizes the military path isn’t right and quits after first year.
- Lost a firing pin during a field exercise, leading to a classic military screaming scene:
Back to Missouri — Success, Failure, and Comedy Dreams
- College Wrestling at Missouri (20:13 – 22:06)
- Wrestled at Missouri, made All-American senior year:
“My senior year I made All-American. I got seventh in the country.” (20:38 – Greg Warren)
- Ryan and Greg bond over once being at the same NCAA nationals in 1990.
- Wrestled at Missouri, made All-American senior year:
- The Wild World of Weight Cutting (27:59 – 32:22)
- Recounts dangerous and comedic extremes of weight cuts using sauna, stationary bikes, and live albums:
“We’d seal off the showers with a tarp… put on Scorpions Live… It was the first spin class” (28:39 – Greg Warren)
- Recounts dangerous and comedic extremes of weight cuts using sauna, stationary bikes, and live albums:
Food, Mental Health, OCD & Binge Eating
- Unhealthy Relationship with Food (32:27 – 38:40)
- Wrestling left a lasting negative impact on his relationship with food; emotional eating and binge cycles ensued.
- Hilariously recounts buying Oreos to supplement Jack in the Box Oreo shakes, and the time his therapist fell asleep during a session about cookies:
“The dude fell asleep… I go, yeah man, I just like Oreos. I’m a grown man in here talking about eating cookies.” (39:37 – Greg Warren)
- Therapy Failures and OCD (Scrupulosity) (41:01 – 49:09)
- Explains a form of Obsessive Compulsive Disorder called “scrupulosity”—obsessive guilt over things he may or may not have done.
- Wrestling and compulsive eating were coping mechanisms:
“I might be a criminal… Life’s over. Just go eat a bunch of Ding Dongs.” (44:23 – Greg Warren)
- Eventually gets proper diagnosis and some effective treatment through exposure therapy.
Bonds, Grief, & Family
- Losing His Mother (55:30 – 65:33)
- Shares touching stories about his mother’s illness, passing, and their close relationship:
"I wanted to be with her for as much time as I had. It made me realize I didn’t want to be away from my family that much anymore." (58:05 – Greg Warren)
- His mother was a humor columnist; Greg now shares her writing every Mother’s Day and birthday on social media.
- Discusses moving from New York back to St. Louis to be close to family, prioritizing those ties over career chaos.
- Shares touching stories about his mother’s illness, passing, and their close relationship:
- Parental Support (61:33 – 66:52)
- Both parents supported his comedy dreams, but dad was a bit tougher at first.
- Emphasizes how lucky he feels to have come from a loving, intact family:
“I did not [have a terrible childhood]. Thank you for that.” (67:16 – Greg Warren, to his mother before she died)
Notable Quotes & Memorable Moments
- “I made it a lot farther than Shane [Gillis] did. I went a full year [at West Point].”
– Greg Warren (16:52) - “Nobody’s ever sat in that seat and said they could crush the clarinet.”
– Ryan Sickler (13:40) - Comedy through Therapy:
“The dude fell asleep… I go, yeah man, I just like Oreos. I’m a grown man in here talking about eating cookies.”
– Greg Warren (39:37) - Making Sense of OCD:
“You just obsess, like: Did I do that horrible thing? …I just would—life’s over, just go eat a bunch of Ding Dongs or whatever.”
– Greg Warren (44:04) - On Family and Gratitude:
“I did not [have a terrible childhood]. Thank you for that.”
– Greg Warren (67:16) - Advice to His 16-Year-Old Self:
“Nothing is permanent… Whatever this thing is, just go try again… Things usually have a way of working themselves out… It’s never over.”
– Greg Warren (68:46)
Important Timestamps
- Greg Introduces Himself and Background: 04:28
- Family Dynamics, Surprising Youngest Brother: 05:17
- Wrestling Start, State Titles: 07:44, 11:03
- Band Geek & Wrestling Jock Crossover: 13:20
- West Point & Military Anecdotes: 16:49, 17:57
- Blood, Sweat, and Saunas: Cutting Weight: 27:59
- Food Binging, Therapy Gone Wrong: 32:27, 39:37
- Detailed OCD Experience ('Scrupulosity'): 41:01, 44:23
- Losing His Mom – Grief and Family Legacy: 55:30 – 65:33
- Advice to Younger Self: 68:46
Tone & Style
The conversation is candid, irreverently funny, but deeply humane. Both Ryan and Greg trade stories like old friends, with Greg’s humility and self-deprecating humor keeping things light even as they touch on pain, therapy, and grief. The episode balances playful ribbing (“I could crush the clarinet”) with moments of genuine vulnerability and soulful insight. For fans of stand-up or tales of resilience, it’s both poignant and hilarious.
Where to Find More
- Greg Warren’s Special: “The Champ” on YouTube (Nateland Channel)
- Greg’s Site: gregwarrencomedy.com
- Instagram/Twitter: @GregWarren
- Ryan Sickler: @RyanSickler // ryansickler.com
Summary Takeaway
If you’re looking for a funny, relatable, and often moving exploration of the “lowlights” that shape us—and how laughter, family, and persistence can help you thrive—this is a must-listen HoneyDew episode.