150. Michael Ian Black: How to Do Comedy with Your 10 Best Friends

150. Michael Ian Black: How to Do Comedy with Your 10 Best Friends

In the 90s, Michael Ian Black’s college sketch group The State got a show on MTV, spawned another iconic group, Stella, and led to the classic movie Wet Hot American Summer. Now Michael sits down with Mike to talk about how all 11 members of The State have remained friends through the ups and downs of show business. Michael shares his advice on how to keep a comedy group together as well as a marriage, as he and his wife just celebrated 26 years. Plus, jokes and stories about truth or dare, the pros and cons of leaving New York City, and behind the scenes of Michael’s love scene with Bradley Cooper.

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72. Drew Barrymore: Do What You Love

72. Drew Barrymore: Do What You Love

Mike’s first-ever major movie role was in Going the Distance, starring Drew Barrymore. Now, 12 years later, Drew takes Mike through her journey from starring in E.T., to hosting SNL at age 7, to produ...

16 Touko 202256min

71. Alex Edelman Returns: The 25 Word Pitch

71. Alex Edelman Returns: The 25 Word Pitch

Mike welcomes back Alex Edelman. Since his last appearance on the podcast, Alex has opened his solo show “Just For Us,” received rave reviews, appeared on The Late Show with Stephen Colbert and has be...

2 Touko 202252min

70. Judd Apatow Returns (Again): He Has Fettuccine in His Heart

70. Judd Apatow Returns (Again): He Has Fettuccine in His Heart

Judd Apatow returns for a record third appearance in support of his latest New York Times-bestselling book Sicker in the Head. He turns the tables and puts Mike in the hot seat for an interview tracin...

18 Huhti 20221h 3min

69. Atsuko Okatsuka Returns: How to Become Yourself

69. Atsuko Okatsuka Returns: How to Become Yourself

When Atsuko was first on the Working It Out podcast, Mike only knew her from her viral Instagram videos and some of her stand-up. Since then, Mike and Atsuko toured together and their "pandemic friend...

4 Huhti 202259min

68. Taylor Tomlinson Returns: She's Not Like Us

68. Taylor Tomlinson Returns: She's Not Like Us

The last time Taylor Tomlinson was on "Working it Out," she had just released her first Netflix comedy special Quarter-Life Crisis. Now, Taylor returns on the heels of her latest special Look At You. ...

21 Maalis 202248min

67. Lynn Shawcroft: How Mitch Hedberg Wrote Jokes

67. Lynn Shawcroft: How Mitch Hedberg Wrote Jokes

Last summer, Mike revistied to the classic comedy album "Strategic Grill Locations" by his friend, the late great Mitch Hedberg. The listening experience was so transcendsnt that it inspired Mike to c...

7 Maalis 20221h 7min

66. David Cross: Fully Committed Dad

66. David Cross: Fully Committed Dad

This week Mike welcomes David Cross, who is a legend in comedy and also makes cameos in Mike’s dreams. The two comics discuss the origins of Mr. Show, why Tobias from Arrested Development is so differ...

21 Helmi 202247min

65. Jon Laster Returns: Playing Legacy Ball

65. Jon Laster Returns: Playing Legacy Ball

When Jon Laster was last on the podcast in the summer of 2020, Mike and Jon talked race relations in America and the relationship between tragedy and comedy. Now Jon returns to discuss his thoughts on...

7 Helmi 202251min

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