Old Dirty Boston
A podcast remembering the streets, scenes, and stories of Old Boston.
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Myles Connor, Al Dotoli and the Gardner Heist
03/10/2024
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 traded it back to bargain a reduced sentence and $10,000 reward. Al's the man who returned the painting. Miles was also close friends with Bobby Donati, the man I believe stole the Gardner paintings. Myles casing the museum and where he thinks the paintings went. I would like to say a big thank you to Myles, Al, and Courtney for taking time to meet with me. And a big thank you to Anthony Amore for connecting us. If you would like to attend the premier of Al and Myles new movie Rock n Roll Outlaw the Ballad of Myles Davis please purchase tickets in advance at https://regenttheatre.com/details/rock_n_roll_outlaw
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Drew Dunn
11/22/2023
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.
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Old Dirty Boston Podcast Live Nov. 2nd 2023
11/10/2023
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.
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Old Dirty Boston Podcast Live Nov. 1st 2023
11/10/2023
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.
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Vinnie Favorito
10/25/2023
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.
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Dane Cook
09/11/2023
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.
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David Callinan Boston's Best Street Photographer
09/01/2023
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.
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Janet McNamara
08/24/2023
Janet McNamara
In this episode I'm talking to Janet McNamara one of Boston's funnies and most original stand up comics.
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Lenny Clarke and the Ding Ho
08/18/2023
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.
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Sober Dan
10/27/2021
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 it to the show, I'll be there, Dan will be hosting, its gonna be a great night, I hope you can make it.
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Black Comedy Explosion with Jonathon Gates
10/20/2021
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 Carolina and the true heart and soul that he has put into his show the Black Comedy Explosion.
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Tony V - Somerville, Social Work and Stand Up
10/13/2021
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.
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John Tobin Presents
10/06/2021
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.
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"Big D" Hullum II
09/29/2021
"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.
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Demetrius “Big D” Hullum I
09/22/2021
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.
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Audio Ed and the Adventure of Season 6
09/16/2021
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
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Boston Be A Man and Mr. Monday the Breaking Balls Bros.
07/23/2021
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 @breakingballs_ @i_love_mondays
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IRA, Art Heists and the Woman Who Stole Vermeer with Anthony Amore
07/15/2021
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’s infamous Gardner Heist.
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Catfishing with Laura Baldini
05/26/2021
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.
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30 Day Challenge: Sexual Kung-Fu and Quitting Smoking
05/12/2021
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. Members of the audience have called Dan mentally weak, and I don’t think its fair to associate Pure Hemp Smokes with Dan’s weakness. I had a bunch of people try them, some people said they tasted like shit. Other people love them, they say it gave them a feeling of calm and helps replace the buzz they get from a cigarette. I think they taste and smell like the weed I used to buy in middle school. If you’re interested in a tobacco or nicotine replacement, you can order online. Check them out at
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Operation Bad Company
04/21/2021
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.”
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Methadone Mile
03/24/2021
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.
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Foster Care to Fitness w/ Coach Jesse Setaro
03/10/2021
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.
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Ice and Iron
02/28/2021
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 come in and talk to me about why they started ice and iron and how they found the path of self cultivation, breathwork and dunking themselves in buckets of ice. Check @OldDirtyBoston on instagram to watch the full video of our day at Ice and iron.
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The King of Boston Comedy Holds Court
02/17/2021
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.
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North Shore Beefs
02/10/2021
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.
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Barefoot and Pregnant
02/03/2021
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 the people around her didn’t come easy. She fought hard and struggled with life and came out on the other side still searching and seeking and doing her head-stands at 77. If you or anyone you know are struggling in a relationship, with drugs, alcohol or depression, please listen to this episode find your thing and lift yourself up.
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🍄 ODB Mushroom Experience 2
01/27/2021
🍄 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 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 617.767.2842
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🍄 Magic Mushroom Experience
01/20/2021
🍄 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.
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The Neighborhood Restaurant
01/13/2021
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 of to help your local restaurants and staff it will help you both feel better.
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