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Episode 75 — The Heir Cast ft. Dr. Anna Lepeley

Episode 75 is one for the books as we welcome our first ever doctor-turned-comedian — the brilliant and wildly funny Dr. Anna Lepeley. Known as the merchandise mastermind behind Comedians in Drag, Anna pulls up to talk about her journey from practicing medicine to commanding stages, and the slow, intentional transition into the butch doctor she always knew she was meant to be.

We get into her hilarious (and surprisingly thoughtful) takes on drugs — including why she jokes they’re best left to the feline species — plus her biggest pet peeves when it comes to comedy crowds and what separates great audiences from the energy vampires. Anna also shares her favorite cities to visit while touring, stories from life on the road, and how she balances sharp wit with real-world perspective.

Of course, we couldn’t resist some chaos — we wrap things up with a draft of the greatest gays of all time that’s equal parts iconic, hilarious, and unexpectedly educational.

It’s smart, it’s unfiltered, and it’s a reminder that sometimes the most interesting paths are the ones you never planned.

We’re grateful you get to experience this one with us — tap in and enjoy.

— The Heir Cast 🎙️

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