I'm talking with Judd Apatow, who has directed, produced, and written many of the biggest comedy films and hit TV shows of the last two decades. We look at what's funny, why it's funny, and why laughter creates connection. We also uncover that thin line between humor and grief and what it means to tell the stories of our lives in a way that we recognize ourselves and our shared humanity.

Renaissance man, Judd Apatow is back! Judd stops by to talk about directing Pete Davidson and Bill Burr in his new film "The King of Staten Island". 

Writer/director/producer Judd Apatow does not feel hopeful about being Conan O’Brien’s friend.

Judd sits down with Conan to talk about using silence in their work, lifting up comedy stars like Seth Rogen and Pete Davidson, fashion tips from Jon Lovitz, reminiscing about eating, and comic rhythm. Plus, Conan and Sona dish on producer Matt Gourley in his absence.

Judd Apatow has known since childhood that he wanted his career to be in comedy. How he worked to become a force in the industry – and what that journey taught him – forms the core of this in-depth interview, which became the pilot episode of LinkedIn Editor in Chief Daniel Roth’s podcast, “This is Working.” Judd has solid advice about the importance of good mentoring, how (and how not) to make yourself indispensable to the room you’re in, and why sometimes you’re better off ignoring feedback and trusting your work. 

We got some special guests for you on this one, jeans!

Judd Apatow is in the MommyDome and he's brought his friend, comedian Wayne Federman! Judd Apatow is a comedian who has become a mogul as a television/film producer and writer. He's most recently been working on the Pete Davidson movie and gives us some stories from the set, including Bill Burr stories. After reminiscing about Judd's life for a bit, we show Judd some audition tapes from our Cool Guys to see which one he would cast in a film. We also play a few rounds of Horrible or Hilarious to see what Judd thinks.

Brian Simpson is a hilarious comedian who you may have seen at The World Famous Comedy Store or on Lights Out with David Spade. Brian grew up in foster care and found himself getting into a lot of trouble, including shooting a person (on accident.) Brian then found his way into the Marine Corps which turned things around. Brian also helps us get to the bottom of SooWoo and gives some advice to listeners who have recently sent in emails to Tom and Christina.

Judd Apatow (Freaks and Geeks, The 40 Year old Virgin, Knocked Up, This is 40, Trainwreck) is an American filmmaker, producer, actor and comedian. Judd sits down with the Armchair Expert to discuss interviewing comedians as a teenager, what he’s learned from his marriage and the experience of delving into Gary Shandling’s life posthumously. Dax wonders if Judd feels a loss when his projects end and Judd talks about growing up in a spiritual void. The two talk about being children of divorce and Judd talks about his commitment to personal growth. 

Writer, director, producer and stand-up comedian Judd Apatow invites us into his L.A. office for an in-depth conversation about all things comedy. We talk about his new Garry Shandling book and working on his upcoming film with Pete Davidson. Judd also weighs in on the so-called “civil war” in comedy, from fired SNL comic Shane Gillis—who called him “gayer than ISIS” in one of his controversial rants—to Louis C.K., who he thinks still deserves “criticism” for making fun of the Parkland shooting survivors. Plus, Judd looks back on some of his biggest movie hits and reveals the funniest person he’s ever worked with.

Follow @JuddApatow and @mattwilstein on Twitter and @lastlaughpod on Instagram. 

Buy ‘It’s Garry Shandling’s Book’ on Amazon.

Read Matt’s profile of comedian Gary Gulman at The Daily Beast.

Highlights from this episode and others at The Daily Beast.

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Writer, director, producer Judd Apatow (Knocked Up, The Larry Sanders Show, The 40-Year-Old Virgin, Girls, Anchorman, Trainwreck) discusses comedy, mental health and politics. Al laughs and gets depressed.