Tom Kelly has been a man in professional and mid life crisis since the pandemic hit five years ago—and he's been trying to make sense of the world ever since. In this heartfelt and funny episode, Tom shares a personal story about why he trusts psychic medium Winter Brook Ryan. Based in Northport, Long Island, Winter Brook explains what it really means to be a psychic medium and why she left behind a career as a lawyer to pursue her calling. Tom asks some personal questions about where to take his life in the next year and gets a message from his grandmother. The question is . . . which one?

Winter's Website:

Winter's Instagram:

Winter's Facebook:

Comedian Olga Namer joins Tom Kelly for a wildly funny and disarmingly honest episode of The Tom Kelly Show. They dive into Long Island nightlife, Jewish family expectations, dating disasters, TikTok comedians, and the shame of wearing a Breathe Right strip in bed. The edibles are in full effect, but so is the heart. Comedy, chaos, and a crash course in boiling the perfect egg—this one has it all.

Chanel Omari – comedian, podcast host (Chanel in the City on iHeartRadio), and breakout star of Bravo’s Princesses of Long Island - shares she changed phone numbers and a 9 year old got her phone number. Now her old contacts, celebrities, Real Housewives from Bravo and maybe even Andy Cohen himself might be texting with a 9 year old (thinking it is Chanel). Tom shares his encounter texting with the 9 Year Old who has Chanel's old phone number.

Comedian Olga Namer pops into the New York studio—and pops an edible—for a hilarious, honest, and surprisingly deep conversation. From growing up Orthodox Jewish in Brooklyn to smoking weed (kind of) with Owen Wilson, Olga dishes on life, love, ChatGPT therapy, and being just high enough to spill it all. Tom and Olga explore:

Anxiety and edibles

Why comedians outsource their self-worth

What it means to grow up modern Orthodox

The chaos of dating as a Jewish woman in NYC

The power (and limits) of ChatGPT as your therapist

A week ago, Tom Kelly made a joke about asking President Donald Trump to Save the Massapequa Chief. A week ago, Tom Kelly made a joke about asking President Donald Trump to Save the Massapequa Chief. Tom promised to deliver 100 All American Hamburgers if President Trump saved the Massapequa Chief. Now reality is mimicking comedy . . .

This week, President Trump is in the White House with Fox News’s Brian Kilmeade making it happen. President Donald Trump has asked Secretary of Education Linda McMahon to save Massapequa mascot . . . the Massapequa Chief. The U.S. Department of Education announced Friday it plans to investigate whether New York education officials are being discriminatory by threatening to withhold funding if a Long Island school district doesn't stop using a Native American-themed logo.

Tom and his buddy Steve hit the road to revisit classic Long Island spots like the now-closed Baldwin Coach Diner, Merrick's infamous No Tell Motel (a.k.a. the Short Stay hotel), and the bittersweet farewell at the Massapequa Soccer Shop.

🎙️ Sponsored by Auto Spa, Williston Park 🚘 Fast oil changes. Faster laughs. Comedian Tom Kelly hosts The Tom Kelly Show live from Auto Spa in Williston Park, Long Island, with guest Fat Jay, the ultimate Long Island comic. In this hilarious episode, they attempt to record an entire podcast during an oil change—with jokes, stories, and massages all packed into one chaotic, fast-paced, real-time comedy moment.

Fat Jay on Instagram: @FatJaysWorld

Autospa of Williston Park:

Tom Kelly kicks off a brand-new concept: interview a guest while their car gets an oil change in 10 minutes or less at Auto Spa in Williston Park, Long Island. Today’s guest? Comedian, lawyer, and mom-of-two Carla Oakerson, here to talk comedy, kids, dating disasters, and defending Tom’s honor on Facebook’s Are We Dating The Same Guy Long Island?

Carla Oakerson On Instagram: Carlaoakerson

Autospa of Williston Part: AutoSpaWillis