Choices We Made: Magazine Makeup Artist or Cosmetics CEO? (with Bobbi Brown)

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 choosin…

Choices We Made: Bread Baskets or Bougie Butter? (with Tony Shalhoub)

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 …

Choices We Made: Wealthy or Wise? (with Michael Lewis)

Author Michael Lewis joins Sam to celebrate the 15th anniversary of The Big Short and talk about if we’ve learned any lessons since its publication—like why we so often conflate wealth and wisdom. They discuss why they don’t think anyone would actually prefer to go back 30 or 60 years if they had t…

Act or Direct? (with Michael Showalter)

Comedy legend turned director extraordinaire Michael Showalter joins Sam to talk about how he made this career shift and how he now realizes he hates acting. Michael tells Sam that he’d ultimately like to direct a film in every genre and he hopes horror is next. They talk about how they love travel…

Outraged or Engaged? (with Patton Oswalt)

Actor and comedian Patton Oswalt joins Sam to catch up where they left off during the first Trump administration and how they simply can’t believe we’re doing round two of this shit. They discuss how there’s money in outrage and how it drives engagement, and how news channels take advantage of your…

Choices We Made: Mother or Father? (with Atsuko Okatsuka)

Comedian Atsuko Okatsuka joins Sam to talk about her new special “Father” and why in her relationship she is “father” and her husband is “mother.” They talk about recalibrating your goals once you’ve reached them–like when Atsuko fulfilled her only childhood goal of working at an ice cream parlor. …

City or Country? (with Leslie Bibb)

Actress Leslie Bibb joins Sam while Mercury is fully in retrograde and they quickly agree that their shoulders only fully relax when they’re in the country despite both living in the city.  They talk about being subject to the winds of planetary forces, not being gamblers (they both abide by a stri…

Choices We Made: Caretaker or Comedian? (with Cristela Alonzo)

Comedian Cristela Alonzo joins Sam to talk about her new Netflix special Upper Classy, and how before her career took off she made the life-changing decision to leave LA to become her mom’s full-time end of life caretaker. She explains that she started standup as a way of dealing with the grief of …

Earth or Space? (with Kal Penn)

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…

Bread Baskets or Bougie Butter? (with Tony Shalhoub)

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 …