This week on Hate To Break It To Ya I sat down with Drea de Matteo — Emmy-winning actress, Queens native, Sopranos icon, and one of the most unexpectedly outspoken voices to come out of the COVID era — and the conversation went everywhere. Drea didn't come in with talking points. She came in with a story, and it's a wild one: a foreclosure notice, a flooded house, a lien she needed to pay off fast, and a decision that made headlines around the world. We got into all of it — how refusing the vaccine cost her her agent, her manager, and a string of acting jobs she could have taken; how she went from voting for Biden to campaigning for RFK Jr. to watching the whole political landscape shift under her feet; and how a single bikini photo on OnlyFans paid off a $75,000 lien in 75 minutes. Drea breaks down exactly what was on that page, sets the record straight about her son Blackjack and the viral moment that blew up on social media, and explains why she sees the whole OnlyFans chapter less as a scandal and more as a middle finger to a system that dropped her without a phone call. We also talked about her Queens upbringing, her mother's world in the theater — Herbert Berghoff, Uta Hagen, the whole lineage — and how growing up inside that world made her the last person anyone expected to end up on a fan platform paying her own mortgage. Drea is one of those people who is exactly who she seems like and also nothing like what you'd expect. She's got an Emmy from what is arguably the greatest TV show ever made, she's raising two kids in Laurel Canyon, she's got a t-shirt company, a podcast, and zero interest in playing the game the way the industry wants her to. I loved this conversation. She gave me everything. ⸻⸻⸻⸻⸻ About Drea de Matteo: Drea de Matteo is an American actress best known for playing Adriana La Cerva on HBO's The Sopranos, a role that earned her the Primetime Emmy Award for Outstanding Supporting Actress in a Drama Series in 2004. She has appeared in Joey, Sons of Anarchy, Desperate Housewives, and Shades of Blue, among many other film and television credits. Born and raised in Queens, New York, she is the daughter of a playwright and furniture manufacturer, and grew up in proximity to the HB Studio theater world through her mother's work with Herbert Berghoff and Uta Hagen. She has two children — daughter Alabama and son Blackjack, whose father is musician Shooter Jennings — and is the founder of the t-shirt and media brand UltraFree. Follow Drea de Matteo Instagram: https://www.instagram.com/dreadematteo/ X: https://x.com/dreadematteo ⸻⸻⸻⸻⸻ Timestamps: 00:00:00 – Cold Open: Coffee Stains & First Impressions 00:01:50 – Drea the Groupie: Music, Queens, and Rock and Roll Roots 00:06:55 – Growing Up in the Theater: HB Studio, Uta Hagen, and Hating It 00:13:55 – Sopranos, Staying in Character, and Not Wanting to Be Famous 00:15:55 – COVID Changed Everything: From Checked Out to Wide Awake 00:20:30 – OnlyFans Goes Viral: How It Started and Why 00:27:45 – Losing the Agent, Losing the Manager, and Self-Canceling 00:34:00 – Foreclosure, a Flooded House, and the Trip to Tahoe 00:42:05 – OnlyFans Explained: The Bikini Photo, the Lien, and $75K in 75 Minutes 00:54:05 – Emmy on the Sopranos, Then OnlyFans: What the Industry Did 01:00:00 – Setting the Record Straight: Blackjack and the Viral Moment 01:07:55 – Kids, Social Media, and Living in GTA 01:13:45 – Hollywood, Independence, and Whether the Business Can Come Back 01:25:55 – Witch Hunts, Symbols, and Trying to Understand Everything 01:43:15 – Satanism, Secret Societies, and Participating Without Knowing 01:51:30 – UltraFree, the Podcast, and Wrapping Up ⸻⸻⸻⸻⸻ Support the Pod: 💥 Patreon: patreon.com/thejamiekennedy 🎟️ Tour Dates: jamiekennedy.com 👕 Merch: jamiekennedy.com/merch 📺 Subscribe: youtube.com/@jamiekennedycomedy ⸻⸻⸻⸻⸻ Drea de Matteo, Hate To Break It To Ya, Jamie Kennedy podcast, The Sopranos cast, Adriana La Cerva, OnlyFans celebrity, vaccine mandate Hollywood, Drea de Matteo interview 2026, Emmy Award actress, Shooter Jennings, Hollywood blacklist, Queens New York actress Learn more about your ad choices. Visit podcastchoices.com/adchoices