Khalil and Ben return for more real talk about the absurdities and intricacies of race in America. Each week, they'll invite some of their new best friends, like former Attorney General Eric Holder, restorative justice leader Danielle Sered, and Chicago historian Sherman "Dilla" Thomas for conversations that are at once personal, political, and playful. Some Of My Best Friends Are... Season 2 drops Tuesdays starting November 1st.See omnystudio.com/listener for privacy information.

In the final episode of the season, Khalil and Ben delve into how the “some of my best friends are…” trope functions in the world of comedy, particularly when comics like Dave Chappelle use it as social commentary. Spoiler alert: it doesn’t always work. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Khalil has been dying to talk to Ben about his relationship with Judaism and whiteness all season. In this episode, Khalil and Ben invite Ben’s other best friend Sascha Penn, the creator and executive producer of the television show Raising Kanan, to join the conversation. Together they take a look at Ben and Sascha’s identities and how being Jewish has inspired their writing about race and racism.  Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Reeling from a terrible string of crimes that happened recently in Ben’s neighborhood in Chicago, Khalil and Ben wrestle with the question of how to respond to violence so people can feel safe, without over-policing communities. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Khalil and Ben talk with New York Times journalist and author Jay Caspian Kang about his new memoir, The Loneliest Americans,  and his experience growing up Asian in America. In this episode, the three men — one White, one Black, one Asian — discuss notions of identity that divide the country, and how one race experiences invisibility as a result. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Khalil and Ben talk with two Chicago artists they admire who are calling for justice through their work–in museums and on the streets. Tonika Johnson, an activist and photographer, takes Ben for a drive to describe her latest project, Inequity for Sale, an art project on reparations and housing. Later, Amanda Williams, a Chicago artist, joins to discuss her works, Color(ed) Theory and the Black Reconstruction Collective Manifesto at MoMA.  Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

For nearly a decade, Khalil and Ben have vacationed together at the magical beach town of Oak Bluffs, MA – a historically Black enclave of predominantly-White Martha’s Vineyard. In this episode,Ben and Khalil reflect on the summers they’ve spent there, the transformative beauty of that corner of the world, and the legacy of race and power at the beach.  Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Introducing our new, subscriber-exclusive bonus series, "Some of My Other Best Friends..." Each month, Ben and Khalil invite one of their *other* best friends to talk through unanswered questions and further debate a recent Some of My Best Friends Are... episode. In our first bonus episode, Ben and Khalil are joined by Turner Classic Movies host and Academy Museum of Motion Pictures artistic director, Jacqueline Stewart, for a deep dive on Interracial Buddy Movies.Some Of My Other Best Friends will be available via PushNik – our subscription program on Apple Podcasts. To listen to these bonus episodes, visit our show page in Apple Podcasts and start your free trial. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

In the weeks after the groundbreaking of the Obama Presidential Library, Khalil and Ben revisit the Obama memoirs, Becoming and A Promised Land: Volume I, on how the Obamas talked about race and racism. From Obama’s retelling of the financial crisis to Michelle’s upbringing on the south side of Chicago, Ben and Khalil discuss how American exceptionalism is intrinsically tied to the Obamas’ stories and their vision of America. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Still basking in the glow of the 2021 US Open, Ben and Khalil take a trip down memory lane to talk about what it was like growing up on South Side Chicago’s predominantly Black tennis scene. From Khalil’s mother watching Arthur Ashe in the 1970s, to the Williams Sisters and Naomi Osaka changing the game, they break down why this sport is in a league of its own when it comes to Black female athleticism.  Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.