Old Dirty Boston

Myles Connor, Al Dotoli and the Gardner Heist

  In this episode, I'm at La Scala in Randolph for lunch with Myles Connor and Al Dotoli, two of Milton's most notorious men. One, for robbing banks and priceless works of art from Boston museums. The other, for managing the careers of entertainers like Frank Sinatra, Ozzy Osbourne and Rodney Dangerfield. Dane Cook told me, "Al Dotoli made me an arena comic." Al and Miles were childhood friends. They were in a high school band together. When Myles stole a Rembrandt from the MFA in 1975, he...

Drew Dunn

In this episode I'm talking to Boston Comedian Drew Dunn.  Tune in to hear how he got started in stand-up, and how his Dad watching Twitch, helped him land a dream gig touring around the country opening for Dane Cook.

Old Dirty Boston Podcast Live Nov. 2nd 2023

In this episode I speak with local comedians, Christian Trotter, Big D, the Legendary Vinnie Favorito and more.  We also check back in with Director John Hickey and his heated fued with comedian Tim McKlasky.

Old Dirty Boston Podcast Live Nov. 1st 2023

In this episode I confront Tim McKlasky on his use of the Golden Banana and Film Directory John Hickey expresses his anger. 

Vinnie Favorito

In this episode I'm talking to the funniest man in Boston Comedy, the one and only, Vinnie Favorito.   Vinnie talks about growing up in J.P., his first time seeing stand-up at the Ding Ho, winning the San Francisco Comedy Festival, Vegas, L.A., Foxwoods, and friendships.

Dane Cook

In this episode I'm talking to one of the greatest stand up comedians ever to come out of the city of Boston, Dane Cook.  Dane talks about growing up in Arlington, navigating his dad's alcholism, childhood anxiety, and the importance of drive, determination and will power in the entertainment industry.

David Callinan Boston's Best Street Photographer

In this episode I'm talking to Boston Street Photographer @larrydavey_  or David Callinan.  In my opinion Dave is the best street photographer in Boston.  His style is up close and personal, raw and dramatic.  Dave talks about shooting in New York and Mumbai, India and what he wants to do next.  

Janet McNamara

In this episode I'm talking to Janet McNamara one of Boston's funnies and most original stand up comics. 

Lenny Clarke and the Ding Ho

In this episode I'm talking to the legend of Boston comedy Lenny Clarke about the begining of Boston's stand up scene at the Ding Ho. A chinese restaurant in a Portuguese neighborhood (Inman Sq Cambridge) with western saloon decor.  Hopefully this will the first of a series of episodes on the life and times of Lenny Clarke. 

Sober Dan

In this episode, I'm talking to Dan Hall host of the Weed Game Show who decided to stop smoking weed for 30 days, the longest he's gone since he was 12. Dan also gave up drinking about a year ago and talks very honestly about how alcohol, Adderall and weed have affected him.    All this talk about Boston comedy and comedians wouldn't be complete without a live show. We'll be taping a live episode of The Weed Game Show on December 1st at Laugh Boston.  Tickets are $20. I hope you can make...

Black Comedy Explosion with Jonathon Gates

In this episode, I'm talking to Jonathon Gates host of the Black Comedy Explosion Boston's longest running comedy night, every Wednesday at Slade's 958 Tremont St. in Boston.  I can tell you from experience this is the liveliest room for comedy in Boston, and if you consider yourself a fan of the art of stand-up comedy, I urge you to experience it for yourself. It was an honor and a pleasure to learn more about Jonathon, his journey into comedy, growing up between Boston and South Caroli...

Tony V - Somerville, Social Work and Stand Up

In this episode, I'm talking to one of the original kings of Boston Comedy, Tony V. He talks about growing up in an Italian family in Somerville. The genesis of the Boston comedy scene, originality, sobriety and making a living doing what you love. 

John Tobin Presents

In this episode I’m talking to five time Boston City Council member and owner of John Tobin presents. The largest network of comedy clubs in MA, including, Nick’s Comedy Stop, Laugh Boston and The Comedy Scene.    John talks about growing up in Mattapan, family, foster kids and what it takes to make it in the world of comedy.

"Big D" Hullum II

Tune in for episode 2 with Big D as we dive deeper into how we're going to break the Boston comedy scene, his world of stand-up, building an act and how to make his story his strength.   

Demetrius “Big D” Hullum I

In this episode I’m talking to Boston Comedian Big D. D’s a close friend and our conversation stayed with me, its heavy.  D talks about growing up in Roxbury, making his way down south, cocaine, stuck up kids, losing his mom and finding his freedom on stage.   

Audio Ed and the Adventure of Season 6

In this episode I’m sitting down with Audio Ed Sullivan. Ed has been working with me on the podcast, and we dig into where this project started, where it is today and where it’s headed in the future.    If you want to be a part of the ODB podcast as a guest, a sponsor or to help on the show send me a DM on IG @olddirtyboston 

Boston Be A Man and Mr. Monday the Breaking Balls Bros.

In this episode, Im sitting down with the Boston Be A Man guy and his brother Carlo. They fill me in on how they started their production company Breaking Balls, the I Love Monday’s podcast and their breakout success With over 3 million followers across social media.  Boston Be A man.  If you want to be part of the Be A man Experience send me a DM on Instagram @olddirtyboston I’m giving away 4 tickets to be my guest at their upcoming show August 5th at the Wilbur Theater. @bostonbeaman @br...

IRA, Art Heists and the Woman Who Stole Vermeer with Anthony Amore

In this episode, I’m talking about Rose Dugdale, the wealthy heiress who broke bad with the IRA, dropped bombs on English soil and stole at least one Vermeer. I’m very happy to welcome back on the show a great friend, Anthony Amore, author of his latest book The Woman Who Stole Vermeer and The Director of security and Chief Investigator of Isabella Stewart Gardner Museum.  Don’t miss the later part of the interview when Anthony weighs in on the theory that the IRA were connected to Boston’...

IRA, Art Heists and the Woman Who Stole Vermeer with Anthony Amore

In this episode, I’m talking about Rose Dugdale, the wealthy heiress who broke bad with the IRA, dropped bombs on English soil and stole at least one Vermeer. I’m very happy to welcome back on the show a great friend, Anthony Amore, author of his latest book The Woman Who Stole Vermeer and The Director of security and Chief Investigator of Isabella Stewart Gardner Museum.  Don’t miss the later part of the interview when Anthony weighs in on the theory that the IRA were connected to Boston’...

Catfishing with Laura Baldini

In this episode I'm talking to my dear friend Laura Baldini about why my recent tinder conversations have her ready to call her lawyer. This is the most personal, uncensored, unfiltered podcast I have ever recorded. Buckle up we're going catfishing.  Laura Baldini, Jason Faulkner, Adam Waters. 

Adam Gets Ambushed

In this episode I’m talking to Dan and Adam, about addiction, why we have no sales and doing your own shit.  Starting this podcast I wanted to tell great stories about the underworld of Boston sex, drugs, rock n roll. I didn’t expect that 90% of the interviews I did would circle back to drugs and addiction. I've realized that's where all the crazy shit comes from.  Some people think I’m a fool to let someone fresh out of a drug treatment run the sales for ODB. Unfortunately, most of the ...

30 Day Challenge: Sexual Kung-Fu and Quitting Smoking

In this episode we're talking about our April Challenges, 30 days of Sexual Kung Fu - Hi Ya! Learn about my month studying the book Taoist Secrets of Male Sexual Energy and Dan’s absolute failure of an attempt to quit smoking with the help of Pure Hemp Smokes. The guys at Pure Hemp Smokes sent us a bunch of packs to help Dan quit smoking. It's basically weed with no THC, just CBD. Dan said they didn’t help him quit, but I don’t think its fair to blame Pure Hemp Smokes for Dan’s shortcomings....

Operation Bad Company

In this episode I’m talking to Shawn Keefe a son of Lowell. Shawn talks about growing up with an alcoholic father, selling drugs, using drugs and how the FBI and DEA came down on one of the largest Fentanyl distribution rings in New Engalnd, operation “Bad Company.”

Methadone Mile

In this episode I’m previewing the final cut of our video from methadone mile. I asked my friends Adam Waters, Dan Hall and Jason Griffin to have look and give me their opinions. The video is intense and as you’ll hear in this conversation, it didn’t leave any of us feeling easy. You can watch the full cut on the Old Dirty Boston Youtube page titled Field Tripping: Methadone Mile. It was definitely the most intense project we’ve worked on for ODB and you can hear why in this conversation.

Foster Care to Fitness w/ Coach Jesse Setaro

In this episode, I'm talking to my friend Coach Jesse Setaro, the owner of North End Fitness. Jesse shares his story growing up with parents that struggled with addiction, foster care, mental health, self medicating and finding salvation in the gym. 

Ice and Iron

Healthy Body, Healthy Mind.   The world’s shut down, I’m stressed, money, relationships. It all gets a little heavy for me. I had to break out of this funk, clear my thoughts and start feeling good again. I pulled some friends together and took a field trip to see the boys at Ice and Iron, Eddie Madden, Jordan Chartier and Rob Carney. Ice and Iron is a half day retreat with a combination of exercise, breathwork and ice baths. I had an amazing experience at their place I asked them to com...

🍄 Laura Baldini: Sex, drugs and in control

In this episode of the ODB mushroom experience, I’m sitting down with the one, the only, talented and beautiful Laura Baldini. This was the first time Laura and I met, but I felt like we were old friends. We both opened up about sex, love, relationships and all the crazy ways we’ve tried to escape the bad and feel the good. I really respect and appreciate Laura for such an amazing interview, it takes a lot of courage to open yourself up for the world to see. 

The King of Boston Comedy Holds Court

In this episode, I’m talking to Steve Sweeney, the undisputed King of Boston Comedy. Steve sits down with three up and coming Boston comics LLoyd Legacy Sharp, Demetrius “Big D” Hullum and Quincy’s own Dan Hall.  Steve talks about the love, craft, artistry and high of stand up comedy. If you love and appreciate comedy, this episode is for you.

North Shore Beefs

In this episode I'm talking to the founder of North Shore Beefs the one and only Angry Andy Ferg. Andy is in the studio with Matt Fitzmaurice, to talk about how their 25k member FB army was shut down and censored without notice and where you can get the best beefs in New England. Step behind the scenes of North Shore Beefs for the best fights, food and go fuck yourselves on the internet.  

Barefoot and Pregnant

In this episode, I’m talking to an important person in my life, my Aunty Diane. Technically she’s my cousin, but that doesn’t really express the relationship. Throughout my life, I’ve watched her move with her own rhythm, her diet, yoga, being a single older woman were all outside the norm and I always respected her courage to maintain those disciplines when it would have been a lot easier to bend to the crowd. As you’ll learn from this episode her strength, courage and deep compassion for t...

🍄 ODB Mushroom Experience 2

Welcome to round two of the ODB mushroom experience. Three brave souls, Alex K, James D and the very funny Dave Russo share their thoughts on life, love and the healing powers of psychedelics.    ODB mushroom podcasts will be an ongoing experiment. If you or a friend would like to be part of an upcoming episode, please DM me on Instagram@OldDirtyBoston   I also have four open spots for new sponsors. If you love the podcast and want to connect with the audience send me a text 617.767....

ODB Mushroom Experience 2

Welcome to round two of the ODB mushroom experience. Three brave souls, Alex K, James D and the very funny Dave Russo share their thoughts on life, love and the healing powers of psychedelics.    ODB mushroom podcasts will be an ongoing experiment. If you or a friend would like to be part of an upcoming episode, please DM me on Instagram@OldDirtyBoston   I also have four open spots for new sponsors. If you love the podcast and want to connect with the audience send me a text 617.767....

🍄 Magic Mushroom Experience

Welcome to the first episode of the Old Dirty Boston magic mushroom experience. In this episode, you’ll take a trip with local comedians Dan Hall and Demetrius “Big D” Hullum, the Real Estate Cowboy Marcus Walker and host Jason Faulkner. Sit down, strap in and enjoy the ride.  

Magic Mushroom Experience

Welcome to the first episode of the Old Dirty Boston magic mushroom experience. In this episode, you’ll take a trip with local comedians Dan Hall and Demetrius “Big D” Hullum, the Real Estate Cowboy Marcus Walker and host Jason Faulkner. Sit down, strap in and enjoy the ride.  

The Neighborhood Restaurant

In this episode I'm talking to Shiela Borges owner of the famous Neighborhood restaurant in Somerville's Union Sq. I've been going the neighborhood since I was a kid, and I was blown away to learn about the family and the history behind one of my favorite restaurants. This is a story of family, hard work, addiction and perseverance.    Please take it seriously how hard it is for restaurants right now consider being part of #wickedtipper eating out or ordering in or anything you can think...

Top of the Food Chain

What happens when you need drugs and you can't pay for them? My next guest decided to take them by force. Buckle up for a wild ride inside a world of drugs, death, violence and family values. This is top of the food chain.   

Beanshooter Off the Rails in Lowell: The Legend of Mike Lee LFG

In this episode, I talk with Mike Lee from Lowell. This is a story of drugs, prison, addiction and redemption.

Off the Rails in Lowell: The Legend of Mike Lee LFG

In this episode, I talk with Mike Lee from Lowell. This is a story of drugs, prison, addiction and redemption.

Burn Boston Burn

In and around Boston, between 1982 and 1984, 264 fires were intentionally set. Wayne Miller, former ATF agent and author of the book Burn Boston Burn, talks about the investigation of the fires.

Addicted to Hookers

In this episode I'm talking to a man who shall remain anonymous. He talks about his crazy ride through the combat zone, cocaine, craigslist and addiction.

R.I.P. Brian Buckley

In this episode, we explore what happens when someone gets charged with Operating Under the Influence.  Brian unexpectedly passed away in October, he was my friend and I miss him  very much. If you know someone have a tough time, just tell them you love them. 

Lydia Shire: The Queen of the Boston Food Scene

On this episode, Lydia Shire, Chef/Owner of Scampo Restaurant talks about her distinguished career at many of Boston's finest restaurants.

Cocoanut Grove Fire

On this episode, Zachary W. Graves-Miller discusses the Cocoanut Grove Fire as well as his new film Six Locked Doors. Six Locked Doors explores the events leading up to the deadliest nightclub fire in American history on November 28, 1942 at the Cocoanut Grove nightclub in Boston, Massachusetts, and the ensuing consequences of a tragedy that left 492 people dead.

Life and Death

Before this podcast Johnny Bowen was diagnosed with stage four terminal cancer. I'm grateful for his story of ambition, addiction, recovery, and love.

The Naked i

I talk a lot about Bostons old Combat Zone, in this episode I'm talking to a man who had a front row seat running the Naked i.

Chelsea Fires

The Great and Powerful Nick Dipaolo

I am honored to have the great and powerful Nick Dipaolo on the podcast. Nick talks about growing up in Danvers, the early days of Boston comedy and working with legends like Louis CK and Artie Lange. Nick also fills me in on why Steve Sweeney punched him in the stomach after a night out in Southie.

The Great and Powerful Nick Dipaolo

I am honored to have the great and powerful Nick Dipaolo on the podcast. Nick talks about growing up in Danvers, the early days of Boston comedy and working with legends like Louis CK and Artie Lange. Nick also fills me in on why Steve Sweeney punched him in the stomach after a night out in Southie.

A Joke A Day

Brian Kiley is the head monologue writer for Conan O'Brien, he talks about growing up in Newton, doing stand-up at the Ding Ho and moving to New York to work on the first season of the Conan O'Brien show with with comedy legends Louis CK and Robert Smigel.

Jon Soroff

Jon Soroff talks about writing for the Boston Herald and the Improper Bostonian, he is absolutely the coolest guest I've had on the podcast.