A comedy podcast made in Maryland
New people. Weird conversations. No real agenda.
Hosted by Justin Anderson and Mike Caropreso. New full episodes on Mondays.
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Latest full episode
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Pick your poison.
Three episodes. Three different reasons this probably should not work.
When the room becomes a problem
Justin Schlegel joins a conversation that gets dangerously close to explaining why 98 Rock almost fired him.
Thirty-two years for a crime he didn't commit
John Huffington tells the story of a wrongful conviction, survival and what happened after prison.
The episode that explains the show
Start here if you want the clearest version of the people, chaos and conversations that make ITDW what it is.
Filmed in Maryland
What is this?
A conversation show with no respectable exit strategy.
If This Doesn't Work… is Justin Anderson and Mike Caropreso talking with comedians, creators, business owners, survivors, local characters and people with stories too strange for polite conversation.
Some episodes are ridiculous. Some get unexpectedly serious. Most do both before anybody notices.
Justin Anderson
Host. Instigator. Talks with his hands.
Mike Caropreso
Co-host. Producer. Edits under duress.
Work with the show
Guest, sponsor or genuinely strange opportunity?
Use the route you would actually use anyway. No application portal. No form disappearing into the void.