Stephen Root is a genius actor who brought humanity to the character of the outsider.

Comedian/Actor Andy Richter shares stories of fame, fans, and family and being a regular guy in an irregular world.

Funny Actress/Writer/Improviser Jamie Denbo talks about jumping in the water of acting and writing while also trying to have a decent relationship with your kids.
As expected, none of it is easy but Jamie somehow makes it work.

Jay challenges his son, college senior, Charlie Kogen, to list the top 5 things Jay did wrong (and right) as a father. Along the way they talk about pushing your kid too hard, the pain of spending time apart, fear of the future, and the tyranny of expectations.

Lisa Kudrow helped introduce Jay to his wife Brown Mandell, and now 27 year later they are all trying to make sense of it. Brown has issues with Jay. Jay has issues with Brown and Lisa understands them both even when neither is making sense. Tune in to marriage miscommunication on this week’s DBAWJK!

The great writer/actor/food & travel show host, Phil Rosenthal talks Jay down from feeling bad about undeserved success. Phil claims dumb luck is part of the game. They also talk about good times, Jack Benny, spoiled kids, great show-running, enjoying life, being able to connect with people no matter what.

In one of our first recordings, Actor, writer, director, and all around mensh, Greg Grunberg helps Jay settle in on what podcasting is and how it might help get people (and especially kids) more connected in their ever increasingly isolated life. And if we can’t fix that, then maybe, just maybe, we can sell them stuff.

Character actor extraordinaire, Richard Kind, talks about having the authenticity and self confidence to speak his mind and get away with it. He says having a healthy ego and approaching the world with joy give him permission to say just about anything.

Comedy hero and one of Jay’s best friends helps Jay work though the deep mysteries of friendship, UFO’s, their failed hit movie “The Wrong Guy” and how to stay pals for 30 years.

Dana talks to Jay about the ego death of change. You think you’re something and then you’re not. He talks about aging, dadding, growing comfortable with being who is and being damn lucky to be that.

The brilliant Kevin Pollak forgives Jay for being late, talks about poker, growing up in San Francisco, becoming Don Rickles’ buddy, the loss of Matthew Perry, inventing podcasts and only does one Shatner impression on this week’s “Don’t Be Alone with Jay Kogen.”

Josh talks about acting, podcasting, being proudly Jewish without being sure about being Jewish and about not being afraid to tell his friends he loves them.

Comic, author, producer, Wayne Federman discusses if there’s an expiration date to being funny. Are you stuck in your generation or can you speak to a broader audience? That, plus what underwear to sport when shouting “Get off my lawn!” at passing children.

Jay is completely enthralled with the depth of comedian/writer/actor, Pete Holmes, talks about religion, philosophy, keeping your artistic standards high, staying good while being human, the joy of seeing his daughter’s face, and making his new Netflix special not so “death-y”.

Singer-songwriter Aimee Mann explains creativity, writing musicals, knowing how to pick a good writing partner and how Jay should weather the crumbling TV streaming world. Just become a critically acclaimed voice of a generation. Easy peasy.

The funny and fabulous Julia Sweeney helps Jay fight through the fear of people, work, life, aging and the crippling danger of improv groups.

Actor Steven Weber helps Jay negotiate the changes in the business. Meditation, fatherhood, and convinces him that, even though they never see each other, they are true friends.