Sam sits down with ‪@BobTheDragQueen‬ — comedian, activist, and now novelist — to discuss his new book Harriet Tubman Live in Concert. Bob reimagines the abolitionist hero transported to present-day America, where she drops a hip-hop album to inspire a new generation. They explore Tubman’s real-life herstory, her radical leadership during the Combahee River Raid, and what freedom means in 2025. Bob also shares hilarious impressions, hot pop culture takes, and why protest music still matters. Watch the conversation!

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Hello and happy weekend! Sam Sanders here. Let’s start with this week’s episode of the show. After months of chasing, we got Bob the Drag Queen to Santa Monica for a chat. (I know, right?! Exciting!)

We could’ve talked all about RuPaul’s Drag Race. We could’ve talked about his run on another reality show, The Traitors. We could’ve talked about *his* podcast, Sibling Rivalry. 

But we skipped all that to talk about Harriet Tubman. 

Why Harriet? ​​Because Bob wrote a New York Times bestselling novel all about her, called Harriet Tubman: Live In Concert. In the book, the abolitionist comes into the present day, after an event called The Return teleports numerous historical figures into the now. Once she’s here, Harriet Tubman decides to make a rap album about her life, and tour with it, to inspire the people. 

“Maybe Harriet Tubman would not like rap music,” Bob confessed during our conversation. “Maybe she wouldn't like hip hop. Maybe Harriet Tubman is into Screamo. Maybe she's into R&B. Maybe she'd be into country music. Who knows what Harriet Tubman would be into? But I'm into hip hop. I'm into rap music. So this is really just my vision for Harriet Tubman.” (The vision actually includes two rap songs, recorded by Bob, in the voice of Harriet Tubman. You’ve gotta watch.)

My favorite exchange in the episode — besides Bob’s incredible impersonations of Barack Obama, Bernie Sanders, and ME — was Bob reflecting on freedom. There’s a scene that occurs early in the book. Harriet’s returned with a few other free Black people from her time period who become her touring band and entourage. Darnell, a rap producer in the present day who’s been asked to help Tubman make her album, takes one of Harriet’s entourage, Odessa, out in Harlem. 

After a soul food lunch at Sylvia’s, walking through Manhattan, Odessa asks Darnell, “What do you do with all this freedom?” The question stopped me in my tracks when I read it, and it led me to ask Bob this week what freedom means to him. 

“There's so many answers,” Bob told me. “You know, there's Nina Simone who says, ‘Freedom means no fear.’ There's Kris Kristofferson —  Freedom's just another word for nothing left to lose.”

“What is freedom? Freedom is ever-changing. And freedom is kind of like happiness, and it's kind of like success… You can decide what success is to you. You can decide that you're successful by shifting what you feel success is.”

If you want more of Bob (and his dog Cody, who sat with us the entire chat), check out the episode wherever you get your YouTubes or podcasts.

Now, can I ask you a favor? 

Next week I’m interviewing Robin Givhan, my favorite fashion critic ever. Yes, I have a favorite fashion critic. She actually made history when she became the first-ever fashion critic to win a Pulitzer in 2006. 

I’ll be chatting with Robin next week about her latest book: Make It Ours: Crashing the Gates of Culture with Virgil Abloh. Abloh, Louis Vuitton’s first African American artistic director, was a powerful, if controversial, voice in fashion before his death in 2021. We’ll talk about what he changed and what he meant, but I also want to use the chat to just bug my favorite fashion critic with a lot of questions about what the hell is going on in fashion right now.

Why, as a 40-year-old, do I have so much existential angst about finding pants that are the right level of wide-legged to be acceptable in public? Why do I feel like there’s a new fashion micro-trend every seven hours? Why is every other week Fashion Week? Why do the youth love the way my friends and I dressed in 8th grade? How can I buy new clothes without feeling like I’m killing the planet? Are my sunglasses small enough? Am I allowed to buy cheap knockoff clothes from Instagram ads? What the hell is my individual style and how do I find it? What even IS fashion these days, in a cultural moment when everything feels a little… adrift? 

I want to take all of these questions – and yours as well – to Robin. Do you have any fashion questions you’d like to pose to a Pulitzer Prize-winning fashion journalist? Send them to me, and I'll share them with her. Just write back to this email and I’ll see it. 

Alright — with that — happy weekend. Go enjoy your freedom, whatever that means to you.

— Sam

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