Jess Hilarious joins Vlad for a candid conversation about her rise from viral comedy clips to sold-out stand-up shows, acting roles, The Breakfast Club, and her bestselling book *Til Death Do Us Parents*.
The Baltimore native reflects on growing up in West Baltimore, the city’s reputation through *The Wire*, its port culture, crabs, resilience, and the local humour that shaped her career. She also takes on the viral “Aaron earned an iron urn” Baltimore accent challenge, breaking down why the phrase sounds so different in her hometown. Jess opens up about being raised in the church, her faith, her mother’s role as a deaconess, and how her parents’ young marriage, her father’s time in the Marines, infidelity, and divorce influenced her views on relationships, cheating, and family. Vlad and Jess also touch on modern marriage conversations involving Big Tigger and Marcellus Wiley.
Jess Hilarious opens up about graduating high school, bouncing between jobs at McDonald’s, Walmart, Manor Care and Future Care, and why getting fired for stealing pushed her toward an unexpected path in mortuary science. Jess explains what happened during clinicals, why embalming scared her off, and how student loans followed her after she walked away.
The conversation also turns personal as Jess reflects on becoming pregnant at 19 and giving birth to her son, Ashton James, at 20. She discusses the fear of telling her parents, considering abortion, her son’s father wanting the baby, and the complicated relationship that followed, including cheating during and after her pregnancy. A revealing interview about young motherhood, bad decisions, survival, and the early life experiences that shaped Jess Hilarious.