Weekend Plans With ‘Sopranos’ Star Drea De Matteo

Weekend Plans is our exclusive lifestyle feature where we highlight the real off-duty routines of the most exciting people in culture. 

This weekend, Emmy-winning ‘Sopranos’ star and host of the “ULTRAFREE” podcast Drea de Matteo chats with The Daily Wire about embarrassing her kids in the streets of Los Angeles, why mornings revolve around her dog, and how one little “picture in a bikini” earned her the $75,000 she desperately needed to save her house. This Hollywood icon may be outlaw country and mobster royalty, but she’s totally punk rock. 

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Drea de Matteo will be described as a “MILF,” “absolute dreamgirl” and a “booyah hottie” for the rest of time. And she’s perfectly fine with that. 

She joins me on a sunny Los Angeles afternoon from her home office, flanked by an American flag in the next room. Delightful chaos erupts as her rescue dogs Moose, Blankie, and her “Chinese mafia princess Shar-Pei” Lucky Luciana tumble through her eclectic Laurel Canyon house, vying for attention. Drea famously paid off a lien against her home using $75,000 she made in her first minutes on OnlyFans. 

“It was a picture of me in a bikini, man. I paid off a freaking lien in 75 minutes.” She caught flak for the move from Ben Shapiro, among others. It stung, but she doesn’t hold a grudge.

“I got dropped by everybody. In a way that just turned me off so much to Hollywood … All they have to do is tell a Democrat, ‘She didn’t get the vaccine.’ And that automatically pegs you as racist. You’re all the things. You’re a hippie who only eats flowers.”

Drea originally sought out the censor-free OnlyFans platform to host her podcast after being canceled for speaking out against the vaccine. The dip in her income was devastating. 

“They tried to make a story out of it, like female empowerment,” she recalls. “I was like, no, this is not that. I hope you are never in the position that I found myself in at that time. And it was all born out of the vaccine mandates and standing my ground.”

We spitball about her character returning from the dead for a “Sopranos” spin-off, or how a “Sons of Anarchy” reboot might feature her character among the last stars standing by the series’ end.  

The HBO hit that transformed television as we know it, “Sopranos” now streams all day. And it’s keeping Drea’s glamorously mob-adjacent Adriana La Cerva persona fresh in adolescent minds. 

“It is like a phenomenon,” she laughs. “I don’t know if it’s because, you know, I fixed my face a little bit so I still look the same? Teenagers are skidding on the road in California, like ‘Holy sh*t, it’s Adriana!’ And I’m with my 15-year-old who thinks it’s so uncool … He’s like, ‘I gotta watch it. My whole feed is “Sopranos.”’”

Drea laments the fact that her son Waylon “Blackjack” Jennings — whom she shares with Grammy-winning music producer Shooter Jennings — has watched all of “Breaking Bad” but has yet to crack into a single episode of “mommy’s show.” 

Unlike some other celebrities, Drea welcomes enduring notoriety as part of the deal. I almost bumped into her last year at Alice In Chains guitarist Jerry Cantrell’s show in downtown LA. I didn’t want to bug her while she was with her daughter, Alabama Gypsy Rose Jennings, but she says I totally should have.  

“My favorite pastime is to give hugs to fans,” she confirms. “I don’t leave the house very much, but when I do — I’m like the Dos Equis guy — I am stopping and taking pictures with a zillion people. I feel like we’re all just this one big universe and that I can’t just shut people out. They love me, and I have to love them back.”

She keeps things apolitical these days, but she dives headfirst into topics that pique her interest, such as geoengineering and the weaponization of musical frequencies. But as a native of New York City (Drea says her father was “offered a button” from every crime family but the Gambinos), I have to ask if she’s personally offended by New York City Mayor Zohran Mamdani forgetting Little Italy on a map of “immigrant enclaves.” 

“I don’t want to be that person that gets on a soap box about it because that always annoys me, but at the end of the day, we built that city. The skyline, it’s all immigrants,” she says. 

“All of these mayors and governors hate f*cking everyone. I don’t think any of them care about any particular race, nationality, religion. I think they’re all bought and sold, I think they have a script and they f*cking stick to it. He’s the son of a famous movie director. What does he know about running a city? He was hired. I’m an actor — he got hired to do an acting job, too … Maybe I should run for one of these fake f*cking acting jobs and see if they’ll put me in office.”

Drea may be too much of an independent thinker to be relegated to any one box. 

“We are punk rock,” she says. “This is the only version of punk rock left. So if everyone in the f*cking music industry and the entertainment industry is following that protocol, they have left their punk rock credentials behind.”

Nights turn into mornings for the dogs

Drea briefly contemplates her morning routine before offering me the timestamp that’s really on her mind: her college-aged daughter’s latest endeavor.

“My daughter just started driving last week, so I’m a nervous wreck. What I do is I watch her drive on my phone. If she’s in the car alone and it’s late I sit here for 30 minutes if I have to, just watching what street she’s on, following her phone like a psychopath.” Drea laughs.

“She writes me, ‘I got home,’ and I send her a screenshot of her at home, like, ‘I already know I followed you for 30 minutes.’” Drea’s determined to let her daughter grow up under her watchful eye. “Me and a girlfriend were actually sitting at Norm’s Diner until four in the morning while she was at an afterparty, to pick her up and bring her and her buddy home. I want her to have that feeling that I had when I was a kid — that freedom. But at the same time, I can’t really give it to her because I don’t trust people … I am a few blocks away in a car like a psycho.”

Considering Drea’s evening routine, I’m shocked she sees mornings at all. “Listen, I’m not sleeping as well as I used to because I am 54 and that happens,” Drea shrugs. But she shares her earliest hours with her longtime boyfriend, musician Robbie Staebler. “We wake up at nine, sometimes we can even wake up at 11 a.m. It depends on what time we go to bed.” 

“The mornings are always the same,” she tells me. “It’s a cup of coffee, sitting outside on the front deck with all the dogs. The big one doesn’t stop barking. My boyfriend calls them ‘No reason barks.’ She’s just barking in the wind, hitting her tail on the wind chimes. It’s chaos.”

Relaxing into another dimension

For someone battling it out on the front lines in Hollywood, Drea’s a pro at letting negative energy pass on by. “The only thing that really stresses me out are continuous EMFs (Electromagnetic Fields) because I’m always researching or doing my work on a phone or a computer,” she says.

But when she needs a little rest, she picks up one of the “15 different books” she’s currently reading. “I get my little neck light and a book because my house is pretty dark. I can’t have LEDs all over me. I’ll have a bigger headache.”

She’s not kidding when it comes to a diverse collection of reading material, which multiplies as we speak. “I am in all these different dimensions,” she explains of the content she later peppers into her podcast. “I am trying to draw a diagram in my mind and put together pieces of a puzzle from ancient religions, secret societies, astronaut theories, all the different schools of thought, and all the different philosophers.”

“I am reading a hundred different books at once and trying to see where they overlap. People are so afraid of a lot of this stuff and then when you really get into it, it’s like, ‘Oh this isn’t really that scary.’”

Quality time with “la famiglia”

Drea’s mother Donna de Matteo died unexpectedly in 2024. In celebration of her life, and hoping to forge new family memories, Drea took her kids on a six-week adventure through Italy and Greece.

“When I graduated high school, she took me and my friends to Italy, to Capri, because that was her favorite place to go with my dad,” Drea remembers of her mother. “We went with a group of 20 people … it was such a beautiful trip.” 

“Both my parents are gone and I was like, I’ve been broke for a while. I’m taking a piece of this money and going on a trip with my kids because I don’t know if the world’s going to shut down again … and I don’t know if they’ll ever want to go with me again. Right now, they’re still mine and they have to do what I say. So, we’re going to Italy. Now when they talk about it, they’re like, I can’t believe you took us on that trip. It was really worth it.”

But the family already knew how to make the most out of their time together, however luxurious it might be. Especially during lockdown. “We literally ran out of money because of COVID and the foreclosure and everything. So, we did roadtrips nonstop. We would go to Mount Zion or Moab. We spent a lot of time in Utah and Arizona. Lots of national parks and hiking.”

She feels this precious time with her kids slipping away. “Everybody’s busy. I wish I could get them to do more. We’ll see.”

An outlaw legacy

Drea describes how she rearranged an entire room of her house to turn it into a makeshift studio where her boyfriend Robbie’s band could record their latest album. Those tracks are still under wraps, but Drea’s got them on repeat. 

Also on her playlist, her daughter Alabama lends keys to her own New York-style punk band, The Pinups, as well as providing under-the-radar vocals on higher profile projects. Drea’s son Blackjack leverages his family’s outlaw country status, with a decidedly unique spin on his rap track “YUHH.” Drea clearly encourages her kids to blaze their own trails.

“We are outlaws,” she recalls telling Blackjack. “I go, dude, you are part of a crazy legacy. From my dad to Shooter’s dad [Waylon Jennings], even Shooter. We’ve all gone against the system in our own way. So, this is your life, buddy. Like, you’re born into it. And you are already a rebellious maniac. So, embrace it. Don’t believe what your friends say. Find the right people who mirror who you really are.”

She may be a rebel, but Drea lets her heart guide the way. “I lead with one thing no matter what, and it’s love. I know it sounds so corny.” I assure her it doesn’t. “At the end of the day, the only thing that matters is the connection we have with people, how we make others feel, and how we love them.”