Comedy Manager and former Just For Laughs Montreal Comedy Festival Director, Jodi Lieberman joins Dev and Jeremy for a fascinating conversation about the festival, stand-up comedy and talent management. 

Dev and Jeremy continue their conversation with documentary filmmaker, Lisa D'Apolito, about her film LOVE, GILDA. They discuss Lisa's experience meeting Gene Wilder, the discovery of Gilda's diaries and Gilda's battle with cancer. Gilda's Club is a community based organization that provides free, emotional support for people of all ages who have cancer, as well as their families. Watch LOVE, GILDA on Hulu/Amazon.  

Dev and Jeremy talk to Lisa D'Apolito, the filmmaker behind LOVE, GILDA about making the documentary and of course, the life of the much loved comedy icon, Gilda Radner. In the words of Gilda, "Life is short, but funny is forever." 

Does luck create opportunities or are you a follower of the mantra, “The harder you work, the luckier you get?”  Dev and Jeremy discuss how some people have limited capabilities, while others don’t seem to be unaware of their own unlimited potential and inadvertently, don’t capitalize on what could be. The show takes a bit of a turn when Dev’s husband Bruce, catches Dev and Jeremy smoking pot and he doesn’t like it. 

Dev offers Jeremy some insight on how to disconnect from setting yourself up for disappointment and removing limitations.  They also discuss how to live in the present so that one’s self worth isn’t compromised.  Later, Jeremy tests Dev’s ability to define common words in today’s society, such as twerking and ghosting and in return, Dev asks Jeremy to define several funny sounding Yiddish terms.  Dev tries to smoke weed again and insists she’s not feeling a thing (hint: she is).

Taking risks in life and in comedy can be scary, yet also potentially rewarding.  Dev sees risks as opportunities and feels they're necessary in order to develop in comedy. Jeremy believes one way to grow is by putting yourself out of your comfort zone. In the spirit of risks, Dev smokes weed for the first time and reenacts the iconic scene with Jeremy from When Harry Met Sally.

New Year's resolutions, self-sabotage, honest reflections and smoking weed (or in Dev's case, never having tried it) are all part of the conversation. While Jeremy wants to understand how we learn to accept ourselves as good enough, Dev wants to know, "how do you save yourself from yourself." 

Some of the best comedy comes from authenticity and being relatable. In this episode Dev and Jeremy discuss the use of nasty language in stand-up comedy, bombing on stage and forgetfulness that comes with age.

Jeremy celebrates Dev landing roles on Comedy Central’s Broad City and on a short film (Playing With Matches) that is aiming for an Oscar nod. A conversation about sex, dating and relationships dominates this episode, as Jeremy tries to explain why he’s casually dating and Dev entertainingly holds up a mirror. And when Jeremy reveals how he lost his virginity, let’s just say Dev has plenty to say.

In the initial episode, Dev talks about her Jewish upbringing and discovering in her 80s, that people found her funny. Jeremy shares his comedic journey that led him to quit a lucrative job and move across the country. By the end, Dev discovers an ah-ha moment about her past that is influencing her present and future.