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Hey, it's Jeff Zito. Thanks for checking out another episode of the Celebrity Jobber podcast, taking a look at celebrities and how they got started, what their life was like before they were famous, and maybe a big break that changed their life's trajectory. We're streaming on Apple Podcasts, Spotify, Iheart, or wherever you listen to podcasts. Please subscribe. Would love a five star rating and leave a review. Sometimes I'll read them even if they're bad. This review comes from User why you sucksobad oh I thought this was gonna be a bad one, but they wrote how original. I take umbrage with some of the guests being classified as jobbers because some of them are still a list with their respective industries but still worth listening to. Some others will always be a list in a lot of people's hearts, and the rest are still fascinating people who have made an indelible impact on their crafts professions and definitely have a story worth hearing. This is a really great idea and I thank you. Pretty cool. Wow. Thank you for the great review. Why you suck so bad Anyway, nominated for an Academy Award for Best Supporting actress in the 2004 film Sideways. Definitely one of my favorite movies ever. Ever talk about her early life, her parents and what they did for work, her first job and job she had before becoming an actress. We'll talk about her big break and her late brother, the great Michael Madsen, a terrific actor who just passed away a few months ago, not to mention her new movie in theaters now called Sheepdog. She is actress Virginia Madsen and she's my guest this week on Celebrity Jobber, the Celebrity Jobber Podcast With Jeff Zito. If you like what you hear, please subscribe, give a five star rating and leave a review. Check out all our past episodes on Apple Podcasts, Spotify, or wherever you pod. What if these celebrities weren't famous? What would they have become? What was their first job? We're about to find out. Hello, Virginia.
C
Hi, Jeff. Good morning.
B
I'm so happy to talk to you. I have so many questions to ask you. I'm such a huge fan of one of your films, Sideways, and I always wanted to have you on and say, maya, ha. I just. As such a great, great film and just celebrated its, I guess its 20th anniversary a couple of years ago.
C
I know, go figure, right? I. I think, you know, a lot of us from that movie have remained in each other's lives, even if we live in different cities. And because, you know, I think we knew even when we were shooting that that it was a rare experience. And so when we see each other, we're kind of all amazed that, like, everyone's okay and didn't we have a beautiful time in the sun in Santa Ynez?
B
Right.
C
It was just. Oh, it was such a rich experience.
B
Well, I'm really excited to see your new film, which is called Sheepdog. I just got the screener last night, so I'm gonna watch it tonight, but I already watched the trailer, and it real. It seems really heavy. And it kind of reminded me of a scene in In First Blood with Sylvester Stallone when he said, over there in Vietnam, you know, I was in charge of million dollar pieces of equipment, and over here, I can't get a job at a goddamn car wash. And I just, I, I saw the similarities to, you know, to this new movie, Sheepdog, which hits theaters nationwide on the 16th, which is Friday. Can you tell me a little bit about the film?
C
You know, I'm a therapist. She's a therapist in training when we meet her. And this is a story about a young veteran who comes back and is suffering from ptsd, and he gets in a lot of trouble. And. And so it's like you can either go into therapy or you can go into jail. And so he meets this woman and, you know, through gentle encouragement, she gets him to trust her and to tell his story. It's important to say that this film, we don't ever show war.
B
Right?
C
You know, we know that he's been through it, but the movie is about the kind of war they face when they come home because, you know, their soldiers are trained for war. They're not trained to be civilians. So when they come back home, it's like they're. What does their family do, their friends? Like, there's a sense of isolation. And this story is not about his ptsd, it's about his post traumatic growth. This is a guy who makes it. This is a guy who does help. You know, the term sheepdog is. It's sort of. It means protect the herd and face the wolf. And so in a way, our other characters in the movie kind of guide him in that way and he's able to choose life. It's the story of his. A guy who heals and recovers. And that's why the movie has gotten so much support from the veteran community, because we made this movie for them.
B
Very powerful trailer.
C
And it's like you don't have to worry about. Yeah, it's a heavy subject matter, but it's a story that's just simply not told enough about the healing side of it, you know, and we just hear a lot of bad news and we don't hear the good stories like this.
B
Right. Success stories that Sheepdog. The film premieres nationwide in theaters January 16th.
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Celebrity jobber this message is brought to you by the Capital One Venture X Card. Venture X offers the premium benefits you expect, like a $300 annual Capital One travel credit for less than you expect. Elevate your earn with unlimited double miles on every purchase, bringing you one step closer to your next dream destination. Plus, enjoy access to over 1,000 airport lounges worldwide. The Capital Venture X Card. What's in your wallet? Terms apply. Lounge access is subject to change. See capital1.com for details.
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The Celebrity Jobber podcast with Jeff Zito. Can you take me all the way back? Virginia, I saw something so interesting. You grew up in Chicago. Your mom left a career in finance to pursue acting. And she was encouraged by film critic Roger Ebert. Could you tell me a little bit about that? That seems kind of wild.
C
Well, my mother was a writer and she still is. She's 94 now.
B
God bless her.
C
And yeah, God bless her. I'm so glad that she's still with us. And she's doing. She's amazing. And there's a lot of pictures of us of her on my Instagram. And she, you know, she. I had this dream of being a professional actress. That's what I would always say. I never said I want to be a movie star. I said I want to be a professional actress because she was a writer as her chosen profession. So, yeah, she left the corporate world. Single mom, and my dad was A fireman. So it was way out of his wheelhouse. Kids wanted to be in show business, and even my older sister was doing theater in Chicago. But she wanted to, you know, she wanted to get married and have. She wanted to raise children, which is what she did very successfully. And we went into show business with a lot of encouragement and support from my mom. So we. That's. That's rare because I think parents, you know, they're just scared. They're scared for their kids, no doubt, but it makes all the difference when your family is there for you.
B
So you were just. You were just mentioning, Virginia, that you're, you know, father was a fireman, and then, you know, mom was in finance. She was always a writer. That was her chosen profession. But left to get into acting. But the family was very supportive of your dreams. So was there ever, like, a thought in your mind, like a backup plan, or were you just too young at the time, so you were just, like, all in on this acting?
C
Well, you know, there were a lot of people who had discouraging words, and. And they said, you know, you need to have something to fall back on.
B
Right.
C
And as a young person that didn't, like, I don't want to fall back. Right. Like, that didn't seem like a viable plan to me. You know, I'm gonna go to school, and I'm gonna train, and I'm gonna learn everything I can about movie making because I loved movies, and I was a good storyteller, like my dad, right. And so I'm gonna. I'm. I faced it, like, in this very serious, ambitious way. And when I look at young actors, you know, they're so brave, you know, doing something that seems so crazy, and they don't even know they're brave. And I don't think I did either. You know, I mean, my mom, I remember her putting me on the plane to California, you know, with my cat and a teapot, you know? You know, and she managed to save up money and, you know, so I could get my first apartment in Hollywood. And she believed in me.
B
Right.
C
But she taught me to believe in myself.
B
Wow.
C
So I, you know, I had that backup, and I had a big brother that was already doing it.
B
Okay?
C
So, you know, so I'm real close to my sister. You know, it's like, you got to stay close to your family or your chosen family.
B
You're right.
C
It is an interesting profession, and it takes a lot of fortitude, and you have to take care of yourself, like, with a lot of discipline. You have to care for yourself.
B
The Celebrity Jobber podcast with Jeff Szeto.
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Celebrity Jobber can you tell me, Virginia, about your very first job? You know, not in, Was it in acting? Was what was your very first job as, you know, your first paycheck ever? What was it? Was it out of, Was it in acting? Was it, you know, at the mall? What was your very first job?
C
I was the checkout girl at the grocery store.
B
Okay.
C
I found, when I was still in high school, I thought it would be very, and this is funny, I thought it would be very important for me to get like a regular job.
B
Right.
C
Just, you know, with my research as an actress, you know.
B
That's cool. Yeah.
C
And so, yeah, I worked. I worked until I got fired because I was really bad at it. And I, you know, I sort of, sometimes I didn't want to charge people as much as things cost.
B
I wish I had you as my checkout girl.
C
Well, I got in trouble for that and, and then I, I worked like after school on like as a answering service operator.
B
Right.
C
And so I, I, what I did is I did my answering in all different characters with different actors.
B
Oh, that's great.
C
And then the rest of it was waiting tables until I got an acting job.
B
What do you consider your big break, Virginia? What was, was there a moment in time, a phone call, a role? Was there something that changed your life? Can you tell me about, was Dune? Dune?
C
You know, Dune? You know, I was, I was fresh off the plane from Chicago and for all I knew I was playing the princess of the universe with David lynch, who'd done this crazy film, Eraserhead. And I got the role and I got a three picture deal and I sort of came out of nowhere and I was a new kid in town. I was the new shiny toy. And I got. So many doors were opened for me for getting Dune and, and I really didn't have much to do. I mean, I had a monologue at the beginning of the movie and then I was just kind of in the second one. I was supposed to be featured But I was treated like I was one of the stars of the film. So I got to be there and, like, watch all these extraordinary actors and, you know, these gigantic sets. And I was a huge sci fi fan, right? So you can imagine, like, what a dream come true it was. And it really, you know, it was really my big break.
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Celebrity Jobber.
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The Celebrity Jobber podcast with Jeff Szeto, you mentioned earlier, Virginia, you know, your family so close. Your late brother, Michael Madsen. So sorry to hear of his passing a few months ago. Can you tell us something about him?
C
The greatest. Yes, I thank you so much for mentioning because, you know, he was my big brother, you know, and I know that he was. He is the greatest, you know, bad guy and badass. Badass, you know, that his Tarantino knew. I mean, he. He just had this presence. But, you know, he was my big brother. He was everything a big brother should be. You know, he was bigger than life and scary to other people. But for me, he was just so loving. And he was a poet, and he had a poet's soul. He had a sensitivity to the world. And, you know, he left me in good hands with his sons. You know, they all have that in them. And the way that Michael looked at the world was more, you know, the thing. You know, there could be a terrible thunderstorm, and he loved the rain. You know, that's. And he would, you know, dare the lightning to strike again. I mean, that was what he was, a true artist. And it's not easy for someone like that to live in the world, right, because they're so sensitive and they see and they feel everything so deeply. So he really understood, like, what a gift that, you know, I had a brother that was doing the same thing I was doing, right? So he understood what I was going through.
B
And was he like. Was he like the characters he played, Virginia, was he like that? Was he cool? Badass. No, different guy.
C
You know, he once said, I, you know, I think I played a bad guy so long that I became one. And he was so. I mean, sometimes they'll be like a, you know, like someone who was an extra on a film that he was on. And they'll. They'll take a moment to say, you know, your brother was so kind. He was so nice to me. They would never think of that because they would just think of him as being scary and he was anything but. He just knew how to do that. That's what kind. Because he was such a good actor.
B
Yes.
C
And, you know, a lot of those tough guys really are softies in real life. And, you know, especially growing up in Chicago, those of. In that era, you know, men were expected to be men and, you know, and they would strike out before they would, you know, sit down and read a book. You know, that's how you were raised.
B
Right.
C
But Michael was a bookworm. And like I said, he was a poet. He, you know, they. That side of him. And maybe it's just that he had a real understanding of why a villain, you know, was flawed. You know, he understood men like that. It's like he never viewed his villainous roles as bad guys.
B
Right.
C
He viewed them as real men who had, you know, real tragedy. And, you know, he saw the reasons why they were bad guys.
B
He was brilliant, brilliant, brilliant actor. Sonny Black and Donnie Brasco was one of my favorites. And I gotta tell you, Virginia, I'm such a big fan of yours. And Sideways and Sh. Sheepdog, new movie in theaters January 16th. I can't wait to watch it. Thank you so much for your time today.
C
Thank you.
B
Really nice tribute Virginia had for her late brother Michael Madsen. Again, I'm such a huge fan of all of his films. A lot of the roles that he played, especially Sonny Black in Donnie Brasco, Reservoir Dogs. I mean, the list goes on and on. Michael Madsen, a badass. I can even think all the way back to Thelma and Louise and his role as Louise's kind of on again, off again boyfriend. You know, Virginia said he was quiet, he was sensitive, he was a poet deep in thought. He liked the rain. You know, just think of this guy, his black hair, tattoos, leather jacket. Always played that badass kind of tough guy role. And she said he was absolutely nothing like that in real life. So there you go. An amazing actor to be able to pull that kind of character off time and time again. So Virginia's mom and dad divorced when her and her brother Michael were young. Father was a firefighter, and her mother, Elaine Madsen, 94 years old, says she's doing great. She originally embarked on a career in finance, later deciding to pursue more creative endeavors for herself. And in the 60s, she became an acquaintance of Roger Ebert, the film critic who encouraged her to pursue a career in the film industry. So I guess Elaine was always a writer. She became a filmmaker and won an Emmy Award in 1983 for producing the documentary Better Than it has to Be. Virginia said she wanted to become an actress at a very early age, but acting was not her first profession. Well, I guess it was her first profession, but her first paycheck, her first job came as a checkout girl at a grocery store, which I believe she said she got fired from. She might have given some of her friends or people she knew a break on some of the items or forgot to charge them. She also said that she was like a phone operator. Another job she had was as an operator for an answering service. And what I thought was interesting was Virginia said she would answer calls in different accents. So she was kind of working on her craft during that job. She also mentioned she waitressed a little bit, as a lot of actors and actresses do when they get to Hollywood to try to make ends meet in between gigs. She mentioned her big break, absolutely. In the 1984 epic space opera film written and directed by David lynch called Dune, which led to a three picture deal. And as Virginia said, basically the rest was history. Nominated for an Academy Award for best supporting actress in the 2004 film Sideways, starring Paul Giamatti and Thomas Hayden Church, her role as Maya catapulted her into the Hollywood A list. Virginia's new film, Sheepdog, is now in theaters nationwide. Thank you so much for checking out another episode of the Celebrity Jobber podcast streaming on Apple Podcasts, Spotify, iHeart or wherever you listen to podcasts. Please subscribe. We'd love a five star rating and please leave a review. Follow on Instagram, celebrityjobberpodcast or the YouTube channel, which is YouTube.com the sign celebrity jobber and past guests and episodes. You can check them all out online@celebrityjobber.com where did it all start for some of these celebrities? You know, every story's different and that's why I love doing this so much. So again, thank you for listening to another episode of the Celebrity Jobber podcast. Until next week. I'll see you then. I'm Jeff Zito.
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Original Air Date: January 17, 2026
Podcast: Celebrity Jobber Podcast with Jeff Zito
Guest: Virginia Madsen
In this episode, Jeff Zito sits down with Academy Award-nominated actress Virginia Madsen to explore her early life, her path to Hollywood, and the influential moments and people that shaped her career. The conversation highlights Virginia's first jobs, her famous family, her breakout role, and her perspective as both a working actor and the sibling of the late Michael Madsen. Virginia also introduces her emotionally charged new film, Sheepdog, which focuses on the recovery and resilience of veterans.
On Sideways and friendships:
On family support:
On not having a backup plan:
On Michael Madsen:
On her Dune experience:
On her first job:
The conversation is warm, candid, and heartfelt, especially when covering family and memories of Michael Madsen. Virginia’s humility and gratitude are evident in her reflections on her early struggles, family, and the responsibilities of being an artist.
This episode showcases Virginia Madsen’s tenacity, humor, and humility as she recounts her journey from checkout girl to Hollywood veteran. Listeners get a sense of her strong family ties, her deep respect for her late brother Michael, and a behind-the-scenes look at her career’s pivotal moments. Virginia’s new project, Sheepdog, exemplifies her commitment to telling impactful, uplifting stories—particularly those that honor the healing journeys of veterans.