Comedian Samantha Bee Stole Cars Before She Turned 16: 'I Learned Pretty Quickly That Was Not the Life For Me'

Long before she became the host of Full Frontal With Samantha Bee, worked on The Daily Show, or started her family, comedian Samantha Bee lived life on the wild side with a stint as a pearls-wearing car thief as a teen.

"I looked really clean cut," Bee told Parents digital content director and host Julia Dennison on the latest episode of Parents's podcast We Are Family. "I understood how to get along socially. I understood how to fit in places in kind of a chameleon way. And then, I fell in with a crowd, I guess. I had a boyfriend actually who stole cars. I joined him on that adventure and we did that together."

Now a mom of three, Bee's not shy about sharing her rebellious period—which was over by the time she was 16—with her kids.

"I've spent a lot of time since then reflecting on what my role in this world is going forward because I really have tried to take ownership of the fact that I hurt people," she says. "Not physically hurt people, but it's such a violation to have something stolen, like to be robbed. I've been robbed since then. I've been broken into and it is a real violation. For a short period of time, I lived life as a part-time criminal, definitely, with pearls and a cashmere twin set, for sure. You'd never would've guessed or known. I was a straight-A student too, so balancing all of these different facets of my personality. I learned pretty quickly that was not the life for me. I was pretty wild. Wild times. I wouldn't go back there."

Check out We Are Family Episode 12 now for more with Samantha Bee on raising teens and tweens and the joys of motherhood.

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Samantha Bee: Hi, my name is Samantha Bee and to me family is everything I care about.

Julia Dennison: Hello and welcome to We Are Family. I'm here with an award-winning comedian, writer, producer, political commentator, actor, and TV host, Samantha Bee. You're the longest serving correspondent of The Daily Show. Holy cow.

Samantha: Yes. I know.

Julia: And, of course, host of your own show Full Frontal With Samantha Bee and your podcast Full Release With Samantha Bee. You're mom to Piper, Fletcher, and Ripley, right?

Samantha: Yes, that's right. That's right, you got it.

Julia: Your husband, fellow actor, comedian, Jason Jones, of course.

Samantha: Yes.

Julia: How old are your kids now?

Samantha: Well, I have a 15-year-old, a 13-year-old, and an 11-year-old. 15, 13, 11.

Julia: Well, Sam, welcome to We Are Family. Thanks for coming on.

Samantha: Thank you. Thanks for having me. I'm so excited to be here. I love talking about family stuff.

Julia: Yay!

Samantha: This is exciting.

Julia: So teens and tween. Oh my goodness, that is-

Samantha: Yes.

Julia: I have a 5-year-old, so does it get easier or different? Does it get harder?

Samantha: Teens and tweens. Well, their needs are different and heavier.

Julia: Right.

Samantha: Their concerns are deeper. They're worried about different things. They also don't agree with you about what they should wear or what they should eat or when they should go to bed. It's just sort of different. Obviously. And the worry is greater too because they're a little more independent so I find that I'm worrying about different things-

Julia: Oh, gosh, yeah.

Samantha: ... and they're heavier worries.

Julia: Lack of control. Kind of just letting go I can imagine is a little bit of a process.

Samantha: Yeah, I have trouble with letting go. I really do.

Julia: I remember a child psychologist that we interviewed once was saying that teens want a potted plant parent. In other words, they want somebody to be in their room and be there for them, but not necessarily in their face. But if they need them, they know that they're there and consistently there.

Samantha: And also sometimes they want you to say no but they don't know that they want you to say no. It's not obvious. I see it sometimes where I feel like they're begging me with their eyes to say no to them, but they think that they want me to say yes. Do you know what I mean?

Julia: Yeah, I know what you mean. They're probably going to listen to this and be like, "No, no, no. We definitely don't want you to say no. What are you talking about?"

Samantha: I know. I know.

Julia: You have a recent facepalm parenting moment that you can think of? On top, you're on vacation, so it must just be bliss. Although they always say for parents sometimes it's like is there such a thing as vacation?

Samantha: It's so funny when you go on vacation. You're just so busy. You're still so busy all the time. Usually when we go on vacation now, we like to rent a house and visit a new area. My chore list stays the same. I was explaining to everybody actually not too long ago that I've been doing laundry since they got here. They just didn't notice that I was doing laundry.

Julia: Oh, lord.

Samantha: The clean clothes are just magically appearing for them and they are just like, "Clothes are always clean." And I'm like, "No, no. There's someone making sure."

Julia: My friend's a mom of three and she says the number one thing in her life right now is laundry.

Samantha: Yes, mountains of it all the time and I had this moment with my husband recently where he was like, "I feel like we don't need to have machines running all the time." And I was like, "You know if you really think about it, we're five people. We're a household of five people. That's three pairs of underwear per day times five days." That's 15 pairs of underwear minimally because kids also change their underwear mysteriously all the time anyway because they're like, "I sat on the floor. I changed my underwear." After five days that's 20-plus pairs of underwear alone if you're not keeping up. This isn't the laundry podcast, I understand that. Maybe I'm just obsessed with laundry right now.

Julia: No, no. If you can't keep up you're going to be drowning in that pile of laundry-

Samantha: Totally.

Julia: ...just find your dead body just rotting underneath-

Samantha: Just rotting underneath.

Julia: ... a pile of teenage underwear.

Samantha: 100 percent.

Julia: To rewind, since we're about family as well as parenting, I wanted to talk a little bit about your upbringing.

Samantha: Sure.

Julia: You were an only child, as I understand it, right?

Samantha: Yes.

Julia: And you were raised by a real village

Samantha: A village, yeah. My parents were really young when they had me. Just still in high school really and teen parents.

Julia: This is in Canada?

Samantha: This is in Canada. When I was born, my parents were really young and they were really pretty unprepared, I would say. They needed a lot of backup from, in particular, my mother's parents and, in particular, my grandmother and my great-grandmother for quite some time ended up doing a lot of the parenting. I lived with my grandmother for quite some time before I lived with my actual parents again. It was a kind of a village. I'm close with my dad. I'm close with my mom. I was very close with my grandmother. I'm close with my stepmom. There's just a lot of love. It's just a kind of nontraditional form, maybe. We didn't all have Christmas together. That is true. We didn't all have vacations together. That is true. I bounced around a lot but wherever I bounced to there was always someone there loving me, which is good.

Julia: Yeah, that's good. So did your mom and dad, did they parent very differently?

Samantha: Very, very differently. I think that my grandmother was very traditional. She was actually the secretary at the school that I attended, so she did a lot of the day-to-day stuff just really by virtue of just physically being in my life. We were just together a lot because she made my lunch. I ate lunch with her. I was always really near her. My mother was a lot more freeform. She taught me a lot about independence. My dad was a little more traditional in his style. I got a little bit of everything. I would say that my mom gave me the most freedom and taught me to be the most independent, for sure. But, it really, really was a true blend.

Julia: As an only child, did you feel like there was a ton of focus on you?

Samantha: No, because it was also the '70s, so there's no focus on the child.

Julia: There is but it is free range. Free range parenting.

Samantha: And when I say traditional, I still mean within the context of the '70s where if you were sick or something, you were just home on your own watching TV all day. TV was your main caregiver. That's how you learned how to read by watching The Electric Company. Nobody was making special accommodations for you, for sure. I was just out there sliding around the backseat of a Duster with no seatbelt.

Julia: I love that. I feel like any parents listening who are at all worried about screen time and their kids, hey, Samantha Bee was brought up by television.

Samantha: Oh, boy.

Julia: ... so there's hope for us.

Samantha: I'm telling you. Definitely.

Julia: You said in your first book, I Know I Am, But What Are You, that you were a scary teenager.

Samantha: I was.

Julia: What are we talking about here?

Samantha: Well, I really did enjoy the free range parent. I enjoyed the freedom that was afforded to me at my mom's house. I presented really well. I looked really clean cut. I understood how to get along socially. I understood how to fit in places in kind of a chameleon way. And then, I fell in with a crowd, I guess. I had a boyfriend actually who was just ... stole cars. I joined him on that adventure and we did that together.

Julia: OK. I read that and that blew my mind.

Samantha: Yeah. I talk about it like I don't mind talking about it. I'm not really proud of it. I think it's like an interesting quirk maybe, but I've spent a lot of time since then reflecting on what my role in this world is going forward because I really have tried to take ownership of the fact that I hurt people. Not physically hurt people, but it's such a violation to have something stolen, like to be robbed. I've been robbed since then. I've been broken into and it is a real violation. For a short period of time, I lived life as a part-time criminal, definitely, with pearls and a cashmere twin set, for sure. You'd never would've guessed or known. I was a straight-A student too, so balancing all of these different facets of my personality. I learned pretty quickly that was not the life for me. I was pretty wild. Wild times. I wouldn't go back there.

Julia: Do you feel like you were rebelling a little because you were that straight-A student?

Samantha: I think I was just trying to ... I don't know what I was trying to do. I think in some ways I was aspirational for objects. I was like, "I should have a car." It was the bottomless pit of wants and a person who also couldn't say no very well. If somebody was doing something wild or doing something that we shouldn't be doing, I was always there to just go along with it. In some ways, I probably thought that I knew better than anybody else, so I definitely for a while thought I was a criminal mastermind, which is just not true at all. Just like the complete opposite. I'm very honest with my own kids about all that stuff because it was a pretty brief period. We're talking maybe a year and a half out of my entire life. I was really done with it. By the time I was 16, I was back on the straight and narrow being a normal person again. And so, I'm glad that I had that. Maybe it was more rebellion against society in general. I'm glad that I was done with it on the early side, I will say that.

Julia: Now you have teenagers. First of all, what kind of teenagers are they and also how have you kind of ... Bearing in mind all this from your past, how's that kind of affected how you parent them?

Samantha: Well, the atmosphere of parenting is so different now and I enjoy it so thoroughly. I really love being around my kids. I definitely, one million percent, know that having children was the smartest and best thing that I have ever done. I just feel like it's not talked about enough how enjoyable your own children can be. There's so much conversation about, "Oh, it's like this, and it's like that." But, they're the best campfires I ever made. You know how you just want to stare into a campfire forever?

Julia: Yes. Oh my gosh.

Samantha: Which is not to say that we always agree with each other or get along or sometimes they just actively don't like me. It's such a pleasure for me when we're all together. It's the time when I feel the safest. I just feel like-

Julia: Totally.

Samantha: ... I'm myself more than ... There's no other situation in which I am as fully myself as when I'm with my kids.

Julia: Do you think that your relationship has gotten better as they've gotten older or has it always been that way?

Samantha: It has just deepened. It's just different. Sometimes they have to be mad at you because they just have to be mad at you. Sometimes they're just trying to find something to be mad at you about and you just have to accept that. Sometimes, they're mad at you legitimately because you forgot something or did something or failed at something. It's just like the greatest. It's the greatest journey. It is different because it's not like I'm not the parent. It's not like I'm not guiding them in a way. It's not as free range, that's for sure. And we're really trying to make them know themselves. We're just trying to give them space to know themselves, but also with safe constraints. I feel like, in many ways, I just didn't have a lot of constraints and that was overwhelming maybe.

Julia: You've brought them up here in New York City in Manhattan, right?

Samantha: Mm-hmm. Yes.

Julia: What's your approach to a subway or Uber? Have they been taking them since a younger age by themselves or what are your rules around the city?

Samantha: No. Actually, they haven't had that much freedom around the city. They're getting it now because my daughter's in high school. First of all, the year they really would've probably been exploring a lot more was a COVID year, so-

Julia: Right.

Samantha: My daughter is spending a lot more time independently now. She's going into 10th grade, so she's really excited to live more fully this year. She's just excited to be present in school more than last year. Same with my son. I think they'll experience a lot of that. We've always lived walking distance from their schools. And we love to walk. That's one thing we definitely do. Even though they go to school pretty far away, we always walk anyway and we do that morning walk. Even though it's pretty long, we all try to do it together.

Julia: That's so great. How has the pandemic been for the family? I feel like tweens and teens, it's such a hard age to have to be shut away like they had to be.

Samantha: It was pretty hard on them. They're good independent learners. They're good with the work part of it but, socially, I think it was really challenging. My daughter's 15. She doesn't want to only spend time with her parents.

Julia: Right.

Samantha: Same with my son where he wants to see other boys at school, not just his sisters, which is totally valid. I think that all of these dreams will come true this year. As much as they love spending time with us, and I'm sure that they do, they also definitely want to reject us and they want the freedom to do that.

Julia: To talk a little bit about your relationship with Jason, I think you said something like, "There's never been a successful, happy marriage in your family lineage."

Samantha: Yeah. I did say that. That's true.

Julia: But, yet, you got married.

Samantha: We did.

Julia: Can you talk a little bit about how you guys met?

Samantha: We met doing children's theater, actually. We met doing a really bad production of Sailor Moon. It was a live action-

Julia: Oh my gosh.

Samantha: ... Sailor Moon. It was like… the worst children's theater. Could you even really define it as theater? It was a performance. It was a bad performance. It was not at all love at first sight or anything like that. We didn't really even like each other or talk to each other for a year. It really took a long time for us to even look up from what we were doing to notice each other. And then I started driving him to gigs because I had a car and he didn't. And that's when we just started talking really in traffic.

Julia: A car you purchased, right? You didn't steal that one?

Samantha: No. No, no. That was legitimately a legitimate car, yes.

Julia: I feel like through the pandemic so many people have been forced into living and working with their spouses and their partners and a lot of people ... I'm divorced, so this is not me, but I know a lot of my friends. My friend tweeted something about how she figured out that her husband is a circle back guy when he's on his Zoom calls. It's like you're exposed to this whole working side-

Samantha: Oh, that's funny.

Julia: ... with your spouse, but I feel like you and Jason wrote the book on that. You've been working together for such a long time. He was a correspondent on The Daily Show. You've written movies and shows together…

Samantha: We have always worked together. It's very true. This is our 20th anniversary of being married, so we've been together since 1997. We've always kind of worked together and we took the approach because we spent so much time in Toronto auditioning for things. He would work and then I would get a job. We had a very fluid arrangement of who was working and who was holding down the fort at home and who was earning and who wasn't. Maybe we were both earning or maybe we weren't and we had to lock it down a little bit.

He really taught me how to save money. He actually is an extremely responsible human being, whereas I was not really. I had no concept of saving and just really didn't understand how to do that. I was just broke all the time as a 20 year old. When we started working together, we also started merging our finances. It helped me to really understand how to support him when he needed support. He would support me when I needed support and that fluidity has always followed us in whatever form. I started at The Daily Show in 2003 and then he got hired maybe a year or a year and a half later. I was like, "Oh my God, I can't believe this is happening." It was like a miracle that they hired. I was like, "This is incredible. You've discovered this incredibly talented person who I'm already married to." They're like, "Guess what?" "Oh my God, he's my ..." It was a moment. They saw him. He auditioned-

Julia: That's great.

Samantha: ... and someone was like, "Wait, aren't you married to him?" And I was like, "You discovered my husband. This is incredible."

Julia: That's cool.

Samantha: It was so cool. And then we were like, "Well, if we're going to be working together, we could share an office together then we could get a bigger office." They really were so resistant to putting us in the same office because they were like, "When you have marital fights, it's going to blow up the whole office." We were like, "We know how to work together. We'll share the space very well."

Julia: That's cool. Do you guys parent similar to the way that you work individually? You were saying he's very responsible financially and everything. Is this reflected in his parenting?

Samantha: Oh yeah.

Julia: How are you guys different as parents?

Samantha: How are we different as parents? That's interesting. I don't know. I don't know if I've ever defined it. It's kind of similar. We're a little bit fluid about it. Without talking about it too much, we're actually pretty aligned. Our value system is the same. We love parenting our children the same. We may disagree on little things, but we sorta work it out.

Julia: I could see how working together first and then becoming parents it like probably prepped you pretty well for parenting together because parenting can sometimes, well, a lot of times, feel like a job.

Samantha: I've never thought about it that way before, but I think you're exactly right because we do know how to work through disagreement. Everything has just become a bigger version of what it was in 2001. Our world has expanded so incrementally over time. Our jobs got bigger. And then we had a baby and our family got bigger and then it got bigger again. We've had lots of time to adjust to all these new realities and we've just psychologically adapted as well.

Julia: Yeah. I love that. You've talked about how motherhood didn't change you as a comedian and it didn't change your sense of humor and I love that. I feel like so often everyone gets all serious when motherhood kind of enters the chat, you know?

Samantha Bee: Right. (laughs) Coming from a sketch comedy background you look at everything as an incredible prep. That big belly was the most useful. I loved it. I was like, "All right, this is so awkward. I'm going to run down the street after someone with a microphone." All the producers were like, "Well, yeah, but you can't run. Oh my god, please don't hurt yourself." I'm like, "I can still run. I'm not ill. This is just a condition of being." I was like, "I'm not going to put myself in danger, but if it's my idea to run then I know that I can do it and you have the cameras rolling. I'll do it. It's my idea. Let me try it. I think this is going to look really funny." And it did. And then we had our first baby and then we were like, "Guys, we have a baby. We can use her in things. This is a valuable prop." And then we put her in a couple of things on The Daily Show. And then, a couple of months into that we were like, "She is no longer a prop." She has her own life. I understand now she is actually not a prop that we're not going to use and we're not going to put her on camera anymore. Everybody was like, "Yeah, we figured you'd come to that decision" and we did.

Julia: What do your kids think about what you do?

Samantha: I think they secretly like it, but they're not overly impressed.

Julia: You got to be cool about it.

Samantha: Yeah. I feel like it's-

Julia: Just mom.

Samantha: I'm just their mother and Jason's just their dad. Sometimes people come up to us in the street and they're like, "We love you from the thing" or "We love this thing." They look at our kids and they're like, "You should be so proud of your parents." Our kids are just like, "Oh my God, I'm going to throw up. You don't understand. These are the nerds that sit in my house and tell me to do stuff.

And I do think that that's a better ... if your kids think that you're cool when they're coming up in the world. That's dangerous for them later in life. It's much better for them to just be like, "These two losers? Are you sure you're talking about the right people?" I think they like it a little bit. They probably think it's a little bit cool. I know that they don't tell people what we do. It's not like they're running around going, "Guess what my parents do." They are secretive about it. At some point, my daughter had a class and one of her teachers played a segment from one of the episodes of my show in the class. She didn't even say, "That's my mom."

Julia: Oh my gosh.

Samantha: She didn't even tell anyone. I was like, "Oh my God, that's so exciting. Did you tell ... Does the class know that I'm your mom? That's so neat." She was like, "No, I didn't. Not going to tell anyone." All right, that's fine.

Julia: So, I feel like we've had a lot of heavy things this past year. How do you approach those with your kids talking about race and politics and COVID and sex and all the big stuff?

Samantha: Well, they won't talk to us about sex at all. We've tried to be really open about it with them and they were like, "Please, I want to throw up. I'm going ... Get me out of this conversation immediately."

Julia: Did you ever get to have the birds and the bees conversation? Because does that actually-

Samantha: Oh my God.

Julia: ... really happen?

Samantha: We were so self important about it a few years ago. We were like, "OK, everybody gather around. This is the big talk. We're going to do this. You're all here. You're ready for this." We literally gathered them in a room and we explained where babies come from. We were so, "Let's do this thing" and "Families come in all different shapes and sizes and some ... This is the sperm. Goes into the egg and some families come together in a different way and this is what families are." We were in tears.

Julia: You were prepared

Samantha: This is our-

Julia: You were like, "We're going to do this."

Samantha: We're doing this and they were like, "Thank you," and they walked away. And then about, I want to say, not a year later they came to us and they were like, "Ah, we forgot how babies were made, can you repeat that?" We were like, "You what?" The second time around was much less formal.

Julia: Right.

Samantha: We're like, "I can't believe you forgot this very important thing that we told you. How dare you." They were like, "Ew," conversation over. Well, other stuff, big conversations, we just try to be open to their questions, answer them honestly and bring our own lack of knowledge to the conversation as well. We don't pretend that we have all the answers to the world's problems. I try not to proselytize too much. First of all, we listen to the news constantly in our house. I am always listening to the news. They're receiving a lot of information just via osmosis about what's happening in the world. And then, they're learning about issues at school as well. It's not like I wake them up and give them the rundown, the talking points. You know what I mean? I do let them come to their own conclusions about things. If they have questions, that's great. I often can't answer them.

When it came to COVID, we were just like, "Here's what we think. These are the unknowables. Let's just learn and go together.

Julia: Samantha Bee, you've been so lovely to talk to. My last question I want to ask is just—I feel like you're famously a truth teller. What are some things that you feel like nobody talks about with parenthood?

Samantha: I don't think anyone ever talked to me about how much I would enjoy it. I don't think anyone talked to me and said, "Hey, you're going to love this." I felt like when I was pregnant, the whole time everyone was like, "Don't eat sushi. Blue cheese is going to kill you." And they're like, "Watch out for that moment when you get home and it's just you and a baby and you're not going to know what the hell you're doing." All of that was ... Well, the blue cheese part was not true. I definitely didn't know what the hell I was doing and I definitely did weird things when we first had a baby. I was just like, "I don't want to hurt this angel, this beautiful baby."

We've made terrible mistakes and done stupid stuff, but no one ever said, "Hey, man, these kids are going to make you laugh more than anybody ever. These kids are going to savage you and you're going to be here for it. And you're just going to love watching them grow up." I could've used that. Someone could've told me that part. I felt like I went into it with a lot of fear, which is not to say that all of those feelings are valid. Not everybody has these same experiences. I get all of that, but there is tremendous possibility in making these great people who are better than us. It's like a joy. Making a more evolved version of the people who we grew up to be, that's awesome. They're just throwing away stuff that we all thought was really important and it's such a pleasure to watch them think about gender differently and think about their own personal boundaries differently than we did. That is so exciting. It makes me feel hopeful.

Julia: Sam, thank you so much for coming on the show. It's been so great-

Samantha: Thank you.

Julia: ... talking to you.

Samantha: This was a total pleasure. Thank you so much.

Julia: Thanks so much for listening to my conversation with Samantha Bee

Next time you'll hear from the daughter of musical legend Rick James. Ty speaks candidly about what it was like growing up with a father who was known as much for being a hell raiser as he was a musician.

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