Actor and former Obama White House staffer Kal Penn joins Sam to talk about how he doesn’t make calculated decisions and hates when people suggest he makes a decision tree. They unpack the hope of last week’s elections and his serendipitous decades-long connection to Zohran Mamdani. He explains how every job he’s ever said yes to has turned into subsequent exciting opportunities that have all been meant to be. They wonder if his former job in the White House even exists anymore, talk about the destruction of the East Wing, and the importance of older leaders training their replacements. Plus they argue about the merits of space travel and if we should leave earth or stay on the ground forever.

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For a list of current sponsors and discount codes for this and every other Lemonada show, go to lemonadamedia.com/sponsors.

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Actor Tony Shalhoub joins Sam to discuss living out both their dreams while traveling the world eating bread for his new CNN show Breaking Bread. He talks about how bread is the “OG social media,” and while his bigger decisions have been pretty random, little decisions like ordering off a menu are easy for him—as long as he lets the menu speak to him. Sam tells Tony about how important his film Big Night is to her family, and Tony explains that he’s not a born foodie like co-star Stanley Tucci but is learning to be one. a seminal movie in her and her husband’s life, learning about bread from watching his dad eat it, he doesn’t consider himself a foodie but learned a lot about food from Stanley Tucci, They consider the challenging questions of the day like if young people over-hydrate, the best way to make oatmeal, merits of bougie butter and if bread baskets should be free. Watch Tony Shalhoub Breaking Bread on Sundays at 9pm ET/PT on CNN or stream the next day with CNN’s All Access subscription.

Keep up with Samantha Bee @realsambee on Instagram and X. And stay up to date with us @LemonadaMedia on X, Facebook, and Instagram.

For a list of current sponsors and discount codes for this and every other Lemonada show, go to lemonadamedia.com/sponsors.

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Bobbi Brown, Founder of Jones Road Beauty, joins Sam fresh off the plane from Paris to discuss her new book, Still Bobbi, and to explore her career trajectory from behind-the-scenes makeup artist to two-time cosmetic company CEO. Bobbi talks about how some of her most important choices were choosing men—both her husband, who she knew within weeks was “the one” and Leonard Lauder, who she decided to sell her eponymous makeup brand to when it wasn’t even for sale. They talk about the importance of knowing who you are and when to stop trying out other personas, why at their age it’s necessary to prioritize being able to lift your own suitcase, and the common sense of “no-makeup makeup.” Bobbi tells Sam she is a life-long “non-agonizer” and how her big regret in life not getting a photo with Tammy Faye Baker when she had the chance, and how in her 60s she’s become an accidental Tik Tok influencer.

Keep up with Samantha Bee @realsambee on Instagram and X. And stay up to date with us @LemonadaMedia on X, Facebook, and Instagram.

For a list of current sponsors and discount codes for this and every other Lemonada show, go to lemonadamedia.com/sponsors.

See omnystudio.com/listener for privacy information.