I'm a big Matt Ruby fan and this is his third time on the show!

I have to say—this was pretty funny—comedian Matt and I got high together and went some places I don't think we would have gotten to—for one thing—I said the way he described his dad was hot.

I also check in with him about what Claude AI said when I asked:"What would be good advice to comedian matt ruby from a therapist?"

We talk about a lot of stuff. Matt describes his parents—a free-spirited woman from Manhattan and his dad, a lawyer, a prosecutor. They were introduced by his grandma and fell in love right away, His father loved comedy which was obv a huge influence on Matt.

We also go down a rabbit hole about the ego and the way ego can affect one's own creativity.

There's so much in here—and SO MUCH laughing!

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More about Matt Ruby:

Website: mattrubycomedy

Instagram: @mattrubycomedy

Rubesletter

Latest Special: Bolo

BIO:

Matt Ruby is a comedian from New York City. His smart and dark brand of standup is "button-pushing" and "funny" according to the NY Times. His comedy has been filmed by Comedy Central, MTV, NBC/Seeso, and FOX. His newsletters (The Rubesletter and Funny How) have over 17,000 subscribers combined. He also hosts the podcast Kind of a Lot with Matt Ruby.

His latest standup special is BOLO. Standupworld on BOLO:

“Matt’s a New York comedy beast. He’s sharp, dark, and funny. BOLO is his awesome special on YouTube and it’s something truly worth checking out. It’s Matt at his best: raw, real, and ripping into life’s absurdities with a signature edge the New York Times called ‘button-pushing’ and ‘funny.’ His style’s a mix of cerebral gut-punches and pitch-black humor. We’re diving deep into how he crafted this one, what it’s like to sling jokes in today’s world, and why he’s one of the smartest voices in standup right now.”

Previously: In his comedy doc/special Substance, he performs 4 sets on 4 nights (1 high, 1 drunk, 1 sober, and 1 on shrooms). His previous special, Feels Like Matt Ruby is available on YouTube. His comedy albums (including Feels Like Matt Ruby and Hot Flashes,) are in regular rotation on Sirius and went top 10 on the iTunes Comedy charts. He's also been featured on CNN, The Huffington Post, New York magazine, Time Out, and more. 

He's a regular at the legendary Comedy Cellar and co-produces Hot Soup there (Tuesdays), one of NYC’s longest running independently produced comedy shows, and Good Eggs (Mondays and Wednesdays) at NY Comedy Club. He tours around the country and internationally too. Misguided Meditation is his one-man show about mindfulness, psychedelics, therapy, and death.