The Little Big Bitch: Chelsea Handler

jann (00:01.768)
Okay. Hello. Welcome to the Jann Arden podcast and show. What a goddamn show we have for you today. Listen, this is, don't even listen to any of the other ones. This is the one you want to listen to. I don't need to give this woman an introduction, but I'm going to anyway, because some of you people have not been out of the house since 2019 and you may not know her. An award-winning comedian. Yes, she is. Podcaster, author of six books, six New York Times bestsellers. Try doing that, you jealous

She's hosted late night television. She's done everything from ayahuasca to downhill skiing while holding two dogs, a joint, a cocktail, while in a bikini, no less. She's vaccinated, often horny. She's coming to Vancouver 29th of March, 30th of March, Queen Elizabeth Theater, little big bitch tour. I've seen it, I've seen it. So you got to do it. Please welcome to the stage, Chelsea Handler.

Chelsea Handler (00:56.187)
Oh my goodness, thank you so much. What a wonderful introduction.

Caitlin Green (00:57.288)
Thank you so much. What a wonderful intro. I don't know.

jann (01:01.076)
It's nothing. I had help writing it. I had these two people. Listen, your birthday was epic Chelsea. You were indeed skiing in Whistler with your dog in a backpack. You did have a cocktail. How does it feel? You're on the dark side of 50.

Caitlin Green (01:02.386)
I'm signing up for the UN to help write the United States. Listen, your birthday was happening.

Chelsea Handler (01:06.831)
Yes.

Chelsea Handler (01:21.371)
I am – no, I'm not – I'm on the dark side of it or the light side of it. I'm 49. Is that the dark side of 50? Oh, fuck. Okay. So, yes, I'm on the dark – oh, I didn't know – there's so many sayings in Canada that I haven't really caught on to. I'm so busy smoking joints and drinking cocktails and getting my dogs high that I can't even focus on the lexicon that you guys are using up here. It feels good to be 49. I mean, 50 is a big number. I'm not gonna lie. It does –

jann (01:26.26)
Yes, that's the dark side of 50. That's what they call it in Canada.

jann (01:35.291)
Yes.

jann (01:47.415)
No.

Chelsea Handler (01:48.131)
You're like, wait, what? I remember my dad being 50 and being like, get out of my way. You're old. I don't want to, you know, don't associate with me. So yeah, I am 50, but you know what? I mean, my life just is, I'm happy. I'm so happy. I'm so happy that I am not married and that I don't have some husband that annoys the living shit out of me. I'm happy that I get to have sex with random men in different countries and I don't feel any obligation towards them. I'm happy that I don't have any children of my own, even though I do.

have a lot of children in my life, you know, I do, I actually do more than necessary. But I'm happy about that too. It's like I get to live all out. I get to live the best of all the worlds, right? 
Chelsea Handler (03:09.307)
I think we need to talk about happiness a little bit more and like, you know, unadulterated joy a little bit more and actually finding out in life, especially for women, about what makes you happy and finding your passions and finding your joy and getting after it, you know, because not everybody has the luxury or feels like they have the luxury to do so. And you do. You have every right to create your own joy and find out what brings it up in you because when you are joyful, you spread it.

and you're giving it away to other people. And right there, that alone can never be selfish. So anyone who thinks like, you know, living a life like mine being selfish, it's like, I get to spread this joy with so many people. So there's nothing selfish about that.

jann (03:52.82)
No, creativity. You do bring a lot of joy. I've seen your last two stand-up shows and they were so different from each other in every way, shape or form. It wasn't like you came in and did like anything that was even similar from the show that I saw like 18 months ago. I don't even know how you find the time to do all the shit that you do, but writing comedy, putting a routine together like that, just for people that don't have a clue.

Where does that even start? So you're out on the little bitch, big little bitch tour, and where does the catalyst from that come from? It's a lot about your childhood. I'm not, no spoiler, but how do you put that together? Where does it start?

Chelsea Handler (04:37.147)
I always just take the funny stories that happen. And you know, with my, I'm writing a new book, I'm doing my standup, there's a lot of overlap with those two things. So a lot of like, you know, like the stories I told about going to Kenny Bunkport to George W. Bush's compound, like that's a true story. I was on three edibles and had to go deal with a former president who I have no political amiability with. Like we have nothing, we have nothing in common. And I had to drug myself to go there. And the story of me having to.

jann (04:51.78)
I'm going to go ahead and turn it off.

jann (05:03.978)
As you would.

Chelsea Handler (05:05.419)
And of course, and having to look at his artwork while I was on Three Edibles with him to asking me to take my sunglasses off and me having to tell him, sir, Mr. President, I'm as high as a kite right now. And that's what I had to do to get here. Those stories in my life, like my brothers and sisters were on that trip with me to Maine, and those stories in my life are always, that is my life. It's pure ridiculousness. The situations I find myself in are just crazy. Like my brother is like, listen.

jann (05:14.528)
I hope you enjoyed it.

Chelsea Handler (05:31.851)
He goes, every time we go away with Chelsea, some shit like this happens. And I take pride in that. Like I take pride in providing that kind of entertainment, never being narrow minded enough to not experience something that you think you won't like, always being open minded. And then, you know, my personality leads to a lot of embarrassing situations. And I like to take the piss out of myself. It's fun to self deprecate and be self deprecating.

And a lot of the stories in this show, like the Andrew Cuomo story, the Bill Cosby story, the Woody Allen story, they're all true. So why not share them? You know what I mean? Like everyone wants to know about that kind of stuff. And those people all have, I don't have a ton of respect for, so I have no problem, you know, throwing them under the bus. So yeah, I like to share all of it because not everybody gets to experience all these things. And I'm...

Caitlin Green (06:12.938)
No problem, you know, throwing them under the bus. So yeah, I like to share all of it because not everybody gets.

Chelsea Handler (06:21.995)
I think the reason why anyone is a fan of mine is because they know that I tell the truth. You know, I'm not lying about stuff. I don't make things up. I don't try to make myself look good. I just am living.

Caitlin Green (06:22.318)
I think the reason why anyone is a fan of mine is because they know that I tell the truth. You know, I'm not lying about stuff, I don't make things up, I don't try to make myself look good, I just am living.

jann (06:32.644)
I think one of the things that always strikes me in your shows is how quick you are with hecklers. How quickly, and nevermind that, if this one guy in the Calgary show, he started off really early saying some shit to you and you wound that poor fucking guy throughout the entire show. Like you went back, I don't know, I can't remember what his name was, Rick or something, but it would be this click, and then Rick would get it. And I was just like...

Chelsea Handler (06:56.228)
Who cares?

Caitlin Green (07:00.586)
Click, click, and then Rick would get it. And I was just like.

jann (07:02.22)
But it was perfect and it wasn't overkill because every time you went there and then people started hoping for it. They're like, okay, if Rick dares fucking even lift his shoulder up, he's gonna get it. And, but it doesn't come, there's still a kindness to it and there's a grace to it. And I don't know how that's even possible, but there is because he knows, listen, you know why you bought a ticket to come here.

You're sitting in the front row. Never mind that, you're right in front of me. You're looking at my vagina, basically from where he was sitting. And you...

Chelsea Handler (07:38.671)
Those are top dollar seats.

jann (07:40.576)
They're top dollar seats, but you're so quick on your feet. Were you always like that as a kid? Was 10 year old Chelsea like the kid that was just like, don't screw with me because I will flatten you with words.

Caitlin Green (07:40.692)
Hahaha

Chelsea Handler (07:53.131)
Yeah, I have been very quick. I'm very quick, but not always to my advantage. Sometimes I fly off the handle or historically I have been known to fly off the handle without thinking about what I'm saying. But when I'm on stage, that is my domain and I've been doing it now for 20 something years, 25 and 49, more than 25 years. So if you're not good at your job after 25 years, you should find another one.

And I know how to handle hecklers because it's my show. People are there, they paid money to see me, not to hear him, Rick, talk to me. No one paid for that. So I am also protecting my audience. It's not just about me looking good. It's like, you're not ruining the show for anybody that paid tickets to come see me. And that's how I feel.

jann (08:38.02)
That's the truth. Do you think that the way you were raised, because you did talk about your family a lot and you have talked a lot about your family over the years, do you think your parents and your siblings and the way you guys interacted and the way your parents were with you, that it kind of informed not only your personal life, Chelsea, but your professional life? Like those beginnings of planting a seed of A, you talked about wanting to have some money in your life to not be held prisoner by...

other people's expectations. So that seed was planted early. Your parents have obviously played a big part in that, whether it's good or bad.

Chelsea Handler (09:14.327)
Well, they played a big part in not neglecting me. So that was a big part. And it's not even really, you know, I mean, it is their fault because they should have probably used protection, but they had so many children and they were so tired and they were so inefficient at parenting. Incompetent would kind of be the right word. That I stepped in and parented myself and my brothers and sisters had a big role in parenting me. And there was no loss of love in our family, but there was a loss of like...

jann (09:19.064)
That's good.

Caitlin Green (09:24.151)
They had so many children and they were so tired and they were so inefficient at parenting.

jann (09:31.68)
I'm sorry.

Chelsea Handler (09:40.215)
you know, reliability, dependability, getting picked up on time from school, or, you know, my mom getting in touch with the other kids, mom's friends. My mom's like, I don't, I don't want to deal with those people. Like I'd rather you didn't go to that party. I'm like, no, I need to go to that party. You need to act like a mother and like, you know, step it up. Like my parents were never on the level with the other parents. And that bothered me a great deal. And then I also, the dynamic between my mom and my dad was very obviously in his favor.

And I knew from a very young age that I did not ever want to be reliant on another person, whether it be a man or a woman. Like I was going to make my own way. I was going to have a luxurious life. I was going to have the most fun and I was going to make a lot of money. And so I wanted to do that and I wanted independence. Like when I was a baby, I was so pissed at being trapped in that body. Like I just wanted to be a woman.

I was like, what are these arms and legs? I want my boobs. I wanted my own apartment when I was seven. I asked if I could get my own place because I just wanted to separate from them. I felt like they were holding me back. So now when my brothers and sisters and I, who are all very close, look back or talk about it, it's like now they know that I did know what I was. They just thought I was like this crazy. I was like, no, I told you guys from the very beginning this is what it was going to be and to follow my lead.

If you want to live the good life, come with me and I will show you the way." And my brothers and sisters, some of them were like 15 years older than me and they're like, oh my God, who is this like little, you know, this little lunatic? But now they realized that I knew what it was all along and, you know, now they listen to me a lot better.

jann (11:23.924)
I can't imagine what your report cards were like in elementary junior high. Chelsea is very good, but she just talks too much or whatever.

Chelsea Handler (11:26.719)
Oh, yeah. Yeah.

Chelsea Handler (11:31.467)
A lot of talking, a lot of talking. I wanted to be funny. I wanted people to know I was funny because like the pretty part, because I was always blonde and cute and sometimes I was cuter than others. But I didn't like that attention only. I wanted the attention for being smart and for being funny. So it was so important for me to always, when I was in a new class, I was like, when's my moment, when's my moment? I'm going to make a joke. And I didn't care if the teachers liked me. I just wanted all of the students to know that I was like, I'm the funny one. So like, you know…

And so I would figure out when I was going to say the funny thing. And so I have, yeah, I always had a kind of dominant personality and it's worked well for me in careers. Romantic relationships is a little different because men think they want a woman like me, but then they are with a woman like me and they're like, then they feel some, many men can feel emasculated by that, which is a bummer, but also not my problem either.

jann (12:29.636)
It's not.

Chelsea Handler (12:30.656)
It's not something that I need.

jann (12:33.332)
I was going to say how does money and success affect your personal relationships, but that you've answered the question. And I think that's such a cultural thing too, Chelsea, is that the roles somehow are still so defined in 2024, like she does this, he does that, or whatever the situation is. And plus you're in a situation when you basically live in a glass bowl, you're a little fish swimming around in a glass bowl, and everyone has an opinion about who you sleep with, who you have your relationships with, all of that stuff. I don't even know how you...

how you kind of live your life setting that shit aside and not worrying about what people are interjecting on you. Because you, some of the comments that I've read over the last like three, four weeks, there's a lot of vitriol, even the political stance that you take. I mean, if you're a person that doesn't like Trump, you immediately open yourself up to this maelstrom of the stupidest comments on the planet. And I just want to know how you...

Deal with that if you ever take it with you, if you ever are going to bed with all that shit, people's opinions of you.

Chelsea Handler (13:39.947)
No, I mean, I wish I had this answer because I want every woman to feel this way and not to care so much about what others think. I think that's the biggest issue is that we care so much and we look around and compare and compete. And like, I wish it was an injection, you know, of confidence, of self-assuredness. Like, whatever decisions I make for myself, I'm not worried about what other people are thinking about it. Like that,

left me, I don't even know if I ever really had that, like in elementary school and middle school and high school and those times where you're not fully formed. But once I became fully formed, like I am super confident in the decisions I make. And I know that your attitude is 100% of the equation. If you have a shitty attitude, things, when the things don't go your way, then they go real downhill fast. And if you have a great attitude when things don't go your way, they don't go downhill fast. It's just something that didn't go your way and that's one instance.

and you pick yourself back up with the right attitude and you get yourself back on track. So I don't deliberate, like I don't have a hard time making decisions. I'm very decisive. I know what I'm doing. If I'm writing a book, I'm like, I've got an idea. I have a vision. I'm going to do it. If someone doesn't like it, then they can just talk to me when it's over and we'll discuss it. But I think there's a way of like, I think that, and this isn't something that I've always had like a great positive attitude, but like I don't.

allow myself to get overwhelmed with the commitments that I've chosen to make in my career. I don't want to be the person that goes, I have to go to this event and I have to make a speech. I'm grateful they want me to make a speech. I'm grateful that they're appreciative and I'm grateful that I have the capability to make a speech and to go up there and be funny. So I've spent the last like 10 years of my life after I went to like real therapy, just

Chelsea Handler (15:36.031)
my attitude is it takes precedence over everything. Like it is the thing that informs everything I do. So when I get on stage, I am joyful and I am spreading joy and I want people sitting next to strangers to feel a togetherness that you feel when you're laughing next to a stranger. And I try to take that into everything I do, you know, and you can't obviously have a great attitude 24 hours a day, but you can sure as, like, you can sure as hell try and it makes a huge difference.

jann (16:00.324)
Absolutely. It does make a huge difference. Well, just sitting in the audience, which for me at the show that I just saw on the new tour, I was telling you a little bit that night when I saw you backstage about these four women that were sitting behind me. The joy that they were experiencing was actually pissing off the people around them because they kept repeating every joke that you said. So you would say a line,

And your show's quick. You can't, like, even when you're laughing, you're like, I gotta stop fucking laughing because I'm gonna miss this next thing. So there's a real control that has to go on watching you. It's like, oh my God, what's gonna happen? I gotta make sure I'm listening. These girls were repeating everything. Then they were adding their own take on it. But what my takeaway was, was just that, the absolute joy that these people left. And you see everyone funnel in. You don't get to see that in the lobby. Everyone, the anticipation of the drinks and...

and they've got their, they've just got their Chelsea stories. Everyone's talking about you. And then you do the show and as you're walking out with everybody, the energy is so palpable, the positivity, which we're not used to feeling when we're in groups of people. Usually it's fucking you're protesting something or you're trying to get together to stop something really horrific from happening in the world. But when I was leaving in that group of people afterwards, I just felt like,

This is like a drug and you're right, what the arts does, what creativity does, what laughter does. And people start thinking about their lives differently. So what you're doing is so, it's just important. And I'm not trying to kiss your ass. I just, I felt kind of high when I left because, and I don't do edibles. I don't, I'm as sober as a goddamn judge. Yeah.

Sarah Burke (17:51.594)
And our Jan is very sober. Yes.

Caitlin Green (17:51.602)
I'm sorry.

Chelsea Handler (17:54.046)
I know, Jan is very sober. It's quite disappointing, frankly, but.

jann (17:57.04)
It is disappointing. You would have hated me drunk. I would have been the person that you would have been asking security to remove me. It just.

Chelsea Handler (18:03.071)
Yeah, I can imagine. I can imagine. I'm picturing it now and it's very crystalline.

Caitlin Green (18:05.686)
Ha ha!

Sarah Burke (18:08.858)
Don't worry, Caitlin and I have all the edibles for you. It's good. Ha ha ha.

Caitlin Green (18:10.619)
Yeah, I was gonna say.

jann (18:11.736)
Yeah, no, these guys keep me young because I'm always we talked about drugs like two weeks ago and all their really weird Experiences with mushrooms, but I know Caitlin you wanted to ask Chelsea about Ayahuasca and I want to know that because yeah go

Caitlin Green (18:23.238)
Yeah, I did. Well, this is a great segue. Well, just because I had I've had a bunch of friends actually go to Peru to do ayahuasca. And they have said that it you know, really changed their outlook on their life. And they were obviously going down there with the intention of you know, therapeutic purposes. So I watched

Chelsea Handler (18:40.567)
and getting diarrhea because that's what happens when you do ayahuasca. Although I'm the only person that did not get diarrhea. I just would like to go on the record and say they said, they said, listen, you're probably going to purge, meaning vomit, and you're probably going to, you know, a lot of people shit their pants. And I was like, I'm not a beginner. I am very, very well associated with all drugs and I'm not going to ruin a good buzz by having diarrhea. So just get that out of your head. And guess what? Guess who didn't get diarrhea? This girl.

Caitlin Green (18:45.73)
I was just gonna say.

jann (18:46.202)
Jesus.

Caitlin Green (19:07.81)
You're the only one on Chelsea Does who didn't like either shit or barf into a bucket, which was really something. But did you barf? Okay. Barfing.

Chelsea Handler (19:12.227)
I know. I did barf. I did barf once. So that was, yeah, but that was okay. It wasn't even like, it was just instant and then it was over. I was like, oh, okay, well, whatever.

Caitlin Green (19:21.538)
So when you did it, did you have this like big changing experience and did you go into it seeking something or were you just kind of like, I'm interested in what this is like because I'm kind of that person or?

Chelsea Handler (19:33.319)
I think, excuse me, I think I just want to, like when I do drugs or I do anything hallucinogenic, I just always try to remain open and open, you know, like just be, don't be nervous. If you're scared, that kind of will infuse your experience and I don't, or influence your experience. And I'm not a scared person when it comes to drugs. I like it. And if I don't like something, I just, I won't do it again, you know, and, but I...

I went in just open, thinking it would be about my mom who had passed away or my brother who had passed away when I was a little girl. But it ended up being so much more about my sister, one of my sisters and our relationship. For anyone who hasn't seen it, you can watch it. There's a series called Chelsea Does Drugs on Netflix. It did change my life. It changed my relationship with my sister forever because it just highlighted all of our experiences from being little girls.

Sarah Burke (20:21.254)
Wow.

Chelsea Handler (20:27.187)
on the beach in Martha's Vineyard, like running through the sand, playing with each other. It was like an iPod shuffle of scenes from your childhood that you don't… that were true. Like the bathing suit she was wearing was her bathing suit. The bathing suit I was wearing, the dog we had was the dog we had. Like all of it was just repressed, you know, or somewhere in the back of my brain and I hadn't accessed those memories. And it was a reminder like…

this female voice was saying to me, like you've held hands more with this person in your life than you've held hands with anyone. This is a bond that you have to honour. Your sister's not like you. You have to be kinder and more gentle to her. And I was like, oh, like it wasn't what I was expecting at all, but I didn't, I was, I'm a good student. So I took that and I was like, okay, I'm gonna change. And I did, and I didn't tell my sister what happened because I was like, oh, I'm not apologizing to her. And...

Sarah Burke (21:18.317)
Hahaha!

Chelsea Handler (21:18.403)
But then she saw, when she saw the documentary on Netflix, she called me, she's like, oh my God. She's like, Sissy, you have been so different for the last six months. Like, I can't believe that you didn't tell me about this. She's like, you have been so much nicer to me and so much more understanding. And I was like, well, that's why.

Sarah Burke (21:34.478)
Drugs are good.

jann (21:36.821)
Sisters are complicated.

Caitlin Green (21:36.83)
I do, I mean, yeah.

Chelsea Handler (21:38.959)
They are, but you know, my sisters really aren't. I'm the most complicated one probably. And we have like, I have great sisters. We're very close and we're very tight and we love each other. Like there's no fighting. We don't fight.

jann (21:43.852)
Yes, you are.

jann (21:55.34)
You obviously have really great priorities because I don't know much about you. Obviously I've met you for eight seconds a couple of times, but you seem, what I said to people when I met you the first time, I said she is absolutely the polar opposite of who I thought I would be talking to. And I don't know what I was prepared for. I was, you know, cause I've admired you for so many years and you've made me laugh my ass off. I found you so warm.

Chelsea Handler (22:23.291)
Thank you.

jann (22:25.312)
You look a person right in the eye. You're trying to make sure everyone's comfortable. I think you offered me a drink or a water like six times. What do you need? Sit down, what do you want? Do you want these crackers? I got three grapes left. Like you were just on it. And I found you incredibly warm. And people were like, really? I'm like, yes. And I've spent the last 40 years of my life meeting people, thousands and thousands and thousands of them. And you know,

from being around human beings of what that warmth is and what the authenticity is, because you have done ayahuasca on a goddamn mountaintop and you've dealt with death and you've dealt with hard things. And I think a lot of people skip over the obstacles that successful people have to go through in order to get to where they're going. Not everything is a win. And...

Chelsea Handler (23:22.251)
No, no, no.

jann (23:24.998)
That's the... We learn how to be empathic. That's where we find our characters in the things that we don't get right.

Chelsea Handler (23:31.819)
Yeah, it's like finding your gratitude in the dark. You know what I mean? It's like, listen, if we don't fall, you know, it's almost, it's trite to say, but it's so true. These things, these sayings that we have that seem like, oh, that's such a, like, who cares? What a platitude. It's so true. I've fallen on my face a million times and it's that, thank God, you know, thank God I did because it keeps you grounded and it gets you, it makes you better.

jann (23:56.548)
Thank God.

Chelsea Handler (24:00.631)
You get better every time you fail. When you get up, you are a better person. You are stronger, you're more grounded, and you're calmer because you understand that I can survive anything. I'm 49 years old and I've gotten all of these things because of me. You know, I mean, I've had help along the way, obviously, but I got myself here. So once you realize that about yourself to whoever you are, you're going to be better.

You've gotten through all of these things and you're still here and you're still going. You start to go, wow, I am dependable. I am reliable. These are the things that I've always wanted to be and here I am.

jann (24:41.024)
It's amazing how you can monetize being yourself. It always seems like the weirdest, yeah, the weirdest concept on the planet. People always ask me about, don't you write music for people, for other people? And I'm like, God, no. That was half of the reason that I never really got anywhere in the United States is because after Insensitive in like 1990 fucking six, it was like 30 years ago or something, they wanted another one of those. And I'm like, I don't...

Sarah Burke (24:46.084)
Fuck yeah.

Caitlin Green (24:47.694)
Hahaha!

jann (25:10.452)
want to do that. And I was prepared to die on that mountain. And I'm really not even making it up. I didn't want to do what everybody else was doing. I was just determined to be myself. And it worked out okay. But you've monetized just being yourself. Like, intellectual property is so amazing. To have an idea, put it in a book, put it in a television special, you know, put it into Chelsea Lately, which was a triumph, I might add. The girls and I were talking about this week. You were the only...

female late night talk show that was successful, funny, night after night, kicking ass. I wanna know, I mean, before we let you go, I wanna know what that experience was like, cause I know you're about to produce another television show which we're gonna talk about, but Chelsea Lately was a triumph and you had so many great guests and you nailed it every night by being.

Chelsea Handler (25:58.916)
Thank you.

jann (26:04.48)
yourself and people were generally nervous when they sat in a chair across from you.

Sarah Burke (26:07.834)
Hahaha.

Chelsea Handler (26:08.075)
Yeah. I had no idea how many people were so scared of me, you know, because, because I mean, people still say that they're like, you're so intimidating. I'm like, I'm not intimidating. I'm like, it's so sad on one side of it that confidence is intimidating, like a female who's confident intimidates other people. Like we should want all of our women to be confident. And I'm not, you know, I'm not faking my confidence. It's an eight. I have it, you know, and I've lost it at times in my life and I've had to recultivate it. But

jann (26:12.469)
Scared shitless.

Sarah Burke (26:25.941)
I hear that.

Chelsea Handler (26:38.131)
It was a triumph. It was a huge, fun, crazy experience that I loved. And it was like going to college. Like our offices were ridiculous. We got up to such nonsense. I mean, if we did that today, we would all be fired. Human resources would not. I mean, they used to call us human resources and I would go, I would fuck with them so badly. I would be like...

Caitlin Green (26:54.358)
I'm sorry.

Sarah Burke (27:00.733)
Ha!

Caitlin Green (27:01.151)
Ha ha!

Chelsea Handler (27:03.115)
I mean, I just got so much joy out of taking the piss out of all the corporate people who took themselves so seriously. Because the one thing I do, like, yeah, I take my life seriously, I take my job seriously, but I don't take myself seriously. Like I don't care if I look stupid and I don't care if somebody makes fun of me. Well, I mean…

Caitlin Green (27:06.977)
I'm out.

jann (27:18.848)
You don't look stupid ever and you're smart. And that's, that's the thing is that you're

Caitlin Green (27:20.951)
Hmm

Chelsea Handler (27:23.987)
I have looked stupid. Listen, nobody has never looked stupid. So that's not fair to say because obviously I've looked stupid. I just don't let that define me. Like good, I'm a human being. I can be stupid sometimes. Sometimes I ask really stupid questions and they fly out of my mouth and I'm like, oh, like why did I just say that? But also I have to be able to laugh at myself, right? I have a great sense of humor about myself and about the world. So that's helpful.

And so that was a great experience. I loved doing that show. And then, you know, after seven years, I was like, I'm done, I'm tired. This is silly. I don't wanna make fun of people for the rest of my life. And I wanna do something else. And I was like thirsty for a little bit more knowledge.

jann (28:03.236)
I think it's been a good balance though. Like you said, the Netflix specials that you've done, you know, the whole thing about white privilege and things like that. Yeah, there was some jokes, you know, sort of lofting in through there, but there was some really gut wrenching, hard lessons and things that were kind of like come to Moses moments for you where you were like, okay, I've been put in my place a little bit here and there's some discomfort here. And...

Caitlin Green (28:24.059)
Thank you.

Chelsea Handler (28:29.047)
Uh huh, yeah, for sure. Yeah.

jann (28:32.844)
That was actually really liberating to watch because you knew very quickly it wasn't fucking fun and games the whole time. You were there to learn some stuff, be a better version of yourself and educate whoever else was gonna watch this stuff. And I think we did learn.

Chelsea Handler (28:51.159)
Well, thank you. I mean, that was my intent. You know, after doing something like Chelsea Lately for seven years, I really was, had such a strong desire to be more, you know, serious about stuff. Not only serious, but to learn and to grow and evolve like any of us. We all want to learn and grow. I mean, I'm not trying to stay the same. I'm trying to get better always, you know, more knowledgeable, more empathetic, more understanding, less reactive. So all of the experiences I have, yeah, they have been like across the board.

you know, very different and I'm grateful for that as well. And, you know, now I'm in a situation where I work when I want to work and I, you know, I get to be in Whistler three to four months a year skiing, which is my greatest joy. And I get to, you know, tour or write my books or do my podcasts. It is hard work traveling. It is hard.

jann (29:36.64)
It's hard work traveling. It is hard work moving a body around. So don't think for a second that it's easy because you are away from the people that you love. I don't think your dogs can come with you all the time. And it is tough. You're out there, you're sleeping in a hotel room. And as much as people think that's really glamorous, it's not, it's a hotel room.

Chelsea Handler (29:45.519)
Yeah.

Chelsea Handler (29:51.581)
No, no they can't.

Chelsea Handler (29:58.935)
Yeah. It's a lot of… it's very… it's a lot of tediousness. You know, you're… the planes, the sickness, the… you know, just traveling from time zone to time zone is tedious. Yeah, it's all gross, you know, like it's not… even if you climb privately, it's still gross and tiring, you know, it doesn't matter. All of that stuff is just like… but again, that's an attitude, you know. I have… I know what I need to do. I know that if I…

Sarah Burke (30:09.146)
The feed on the chair. Yeah.

Caitlin Green (30:12.246)
Hahaha

jann (30:17.143)
No.

Chelsea Handler (30:25.935)
conserve, I have to conserve my energy if I'm going to do a show in front of 3,000 people or 4,000 people or a thousand people, whatever it is. I know that I have to, I'm there for them. People save money to watch me and I'm going to deliver. So like my responsibility is to my audience. Whereas before I would be like, oh, I have another show tonight. Like when I was in my thirties, I'd be, I was just like, so I had burned the candle at so many eds that I just had not, I was so depleted that I resented everything. I was like,

can't do this, I can't do that, instead of feeling grateful for having the opportunities to do all of it.

jann (30:58.24)
Imagine even 60, 70 years ago, a single woman doing things in her own terms, having houses, working when you want to work. It's just an unthinkable thing. My mom used to say that to me. Well, dad said that you made more money last year than he did in his whole life pouring concrete. And I burst out crying. Because I just...

was so humbled by her saying that. Can you imagine, Jan, you're living in your own house and you don't even have anyone, no one handed you anything. And had my mom been alive, she would have absolutely loved you. And I knew that she watched your show once in a while. She liked you and she liked Bill Riley. Fuck, sorry, forgive me, but it was, it was just something going on there. But you...

Chelsea Handler (31:49.019)
Two peas in a pod, two peas in a pod.

Sarah Burke (31:50.286)
Yeah.

jann (31:56.624)
I love how you drag your family into your act. And I know we're gonna let you go, but Sarah, I know you wanted to talk about comedy and what the edges of comedy were, and it was your question, and I thought it was great about just what the limits are, and when can you, yeah.

Sarah Burke (32:12.454)
I'm going to combine a couple of things for the sake of time into one question, but there is a line obviously where I'm sure in the public spotlight, it's always like, well, at what point do you get canceled? Right? Like how far can you go? But when it comes to like... I was going to... All good. When it comes to like putting a burn out there because someone has maybe...

Chelsea Handler (32:22.188)
Eh, eh, eh.

Chelsea Handler (32:28.603)
Excuse me, sorry.

Sarah Burke (32:35.566)
you know, taking something you've said out of context. I mean, the Tucker Carlson stuff made me laugh so freaking hard. You're so calculated with the burns. So I'm just wondering what's like your proudest moment in the spotlight and if there is a burn attached to the moment.

Chelsea Handler (32:50.635)
Well, what are my proudest moments? Uh, that's funny. I do like to give it to people, you know, like that. Piers Morgan, Tucker Carlson, those fucking idiots, Ben Shapiro, you know, they deserve it. They, the way they talk about women is reprehensible. And, um,

Sarah Burke (32:52.607)
Of course, of course, of course.

Caitlin Green (32:53.224)
Yeah.

Chelsea Handler (33:20.107)
And I feel a very large responsibility that I've put on myself to always exploit the life that I lead because it is possible and women should have agency. And I want every woman to know that you are not defined by who you get married to or how many children you have or blah, blah. Like there is so much love and joy to be found in this world independent of those things. And so I don't feel like that group of people gets enough support.

So I, cause I get so much feedback from those women, you know, when I do anything of the things I do going, Oh my God, like, thank you for talking about women who don't want to have children that it's not for you. Like that's actually, I'm doing everyone a favor by not having a child. You know what I mean? Cause I wouldn't be good at it. So, uh, and, and if I did have a child, she would be just like me and would be torturing all these men anyway. So what are they complaining about? Yeah, exactly.

Sarah Burke (34:01.92)
Yes.

Sarah Burke (34:15.16)
And you, she'd be torturing you as well.

Caitlin Green (34:16.999)
Hahaha

Chelsea Handler (34:18.135)
I would have divorced her by now, but, but I do enjoy, yes, of course I do. I don't know which, which one my proudest, I mean, I loved going off on Piers Morgan on his show, um, telling him he was a terrible interview. That was a proud moment for me. Uh, Tucker Carlson, same thing, you know, like men who come after me, like watch out because I'm going to make a fool out of you. And I have no doubt in my ability to do so. Like, so I'm not worried about it. So come and get me, you know?

jann (34:18.292)
You gotta... Oh God.

Caitlin Green (34:19.694)
Ha ha ha!

Sarah Burke (34:31.87)
Good. Yeah.

Sarah Burke (34:42.594)
Yeah.

Chelsea Handler (34:46.771)
And that's how I feel. I feel like I'm not just defending myself, I'm defending all of these other women.

Sarah Burke (34:51.894)
And thank you. It's awesome.

Caitlin Green (34:53.025)
Hehehe

jann (34:53.356)
Oh, absolutely. Men are powerful and strong and smart and great business women. And you're a bitch and you are a twat and you are fucking this and that. It's so amazing what the language is that surrounds women that have an opinion, that have integrity, that have intelligence. The verbiage is even different. And it's even different with women, with other women. They're not what you...

Sarah Burke (34:58.49)
Pieces of shit.

Chelsea Handler (35:03.8)
Yeah.

Sarah Burke (35:19.62)
Yep.

jann (35:20.36)
not always supporting each other. I never had trouble with men coming up in the music business, but I sure had trouble with women.

Chelsea Handler (35:25.939)
I know, I had the same experience in stand-up. Same thing, women would be cock-blocking me all the time.

jann (35:29.316)
You know, it was a really bizarre experience. Anyway, you got a lot of things coming up here. The March 29th and the 30th, you sold the 29th out in about a hot minute. You're at the Queen Elizabeth Theater in Vancouver. Those are your two Canadian shows. I can't even look at your schedule because it makes my nipples twist off. It really does. The YouTube theater, you're doing a Netflix, a joke fest in May with.

Sarah Burke (35:29.637)
Wow.

Caitlin Green (35:31.406)
Thank you.

Sarah Burke (35:48.998)
It's

Chelsea Handler (35:49.161)
Oh.

jann (35:57.068)
three gays, a Mexican and a Jew. I'm assuming you're the Mexican. So you're all three Mexicans. Well, a little bit about that. That's coming up. Obviously you're producing it and doing that with Netflix. Is it just a comedy special stand? Not just, it's obviously gonna be hilarious.

Caitlin Green (36:02.382)
I'm not actually all three back kids. We're all three back kids.

Chelsea Handler (36:02.646)
I am. I'm actually all three Mexicans. Thank you.

Chelsea Handler (36:14.975)
It's just like a Netflix is a joke. It's like a night of, you know, they gave me a night and I filled it up with some funny people to do a show. Yeah. And you can catch Dear Chelsea every week. I do my podcast every week, which is also a great joy and I love that. And...

jann (36:25.448)
Love it. We're fans. We loved Monica Lewinsky. Kristin Hannah was fantastic.

Caitlin Green (36:28.206)
Mm hmm. Oh my God, that episode. Monica Lewinsky was so good.

Chelsea Handler (36:31.411)
Yeah, I love Kristin Hannah. Have you read any of her books?

Sarah Burke (36:31.662)
Yeah, so good.

jann (36:34.228)
Yes, she rips my heart out. I just read The Four Winds. I was a little behind with Kristin, but I was just riveted. I read those books in like a day and a half and my eyeballs are going to drop out because I can't put it down.

Chelsea Handler (36:48.963)
Yeah, I know. She's so good. Yeah.

jann (36:50.812)
And you're a big reader. I mean, the fact that one of your favorite books is The Fountainhead, this is a terrible comparison, but my brother who was in jail for murder for 28 years, his favorite book was also The Fountainhead. You share that with him.

Chelsea Handler (37:01.746)
Oh, wow, that's so beautiful.

jann (37:03.88)
Yeah, I'd be remiss to not tell you that while we still had you here.

Chelsea Handler (37:08.031)
Would you, would it be okay for you to give him my number?

jann (37:11.488)
You know what? I did give it to him and you should be hearing from him. Oh, God. If it's a ding, it's him coming on through. It's his birthday today.

Chelsea Handler (37:14.087)
Oh, perfect. Oh, okay, because I just got a text, so that's probably him.

Okay, yeah, yeah. He has an eggplant, he uses an eggplant emoji. Is that your brother? Because I, that's what I… Okay, okay. There's only, there's only eight. So that's probably not him.

jann (37:28.548)
It should be 10 eggplant emojis in a row.

Caitlin Green (37:31.47)
I'm sorry.

jann (37:34.62)
He's 65 today, the poor guy. He's still in a halfway house. And, but anyway, huge reader. And we could talk to you about a million things, but I wanna thank you a million fold for your time. And we're gonna be cheering you on and laughing our asses off. I think you really are such, you are an amazing force and as uncomfortable as you have made me, you've also made me laugh.

Chelsea Handler (37:38.843)
Oh, poor guy.

Chelsea Handler (37:46.983)
Oh yeah, my pleasure, Jan.

Sarah Burke (38:02.959)
Hahaha!

jann (38:03.9)
so much over the years and I'm always, I don't, like I said, I don't know you, but I'm proud of you from the point of being a fellow creator and just watching you go. And there's a lot of inspiration in that. There's a lot to be gleaned from watching another woman stand up for what she thinks is right and just and fair. And you take the heat and you do it with a lot of grace. So.

Chelsea Handler (38:30.628)
Well, thank you so much. Those are such kind words and I really appreciate them coming from you.

jann (38:34.932)
Well, thanks for your time. And I'm sure we'll run into each other again and look after yourself out there. Maybe the three of us should go see her in Hawaii, guys. The little big bitch is going to, it's gonna be in Honolulu, so. Anyway, travel safe. Oh, don't hang up, don't hang up. We're not hanging up. She knows this. She's gonna leave that computer open until it populates. But our guest has been Chelsea Handler, and she's fucking awesome. So go see her little big bitch tour.

Caitlin Green (38:45.026)
Yes.

Chelsea Handler (38:45.235)
Oh yeah, let's go on vacation together. Bring your brother.

Sarah Burke (38:45.991)
Oh, twist my arm.

Caitlin Green (38:47.778)
Ten. Bring your brother up. Ha ha.

Sarah Burke (38:50.999)
Okay, don't hang up don't hang up we need you to load Thank you

Chelsea Handler (38:53.996)
No problem.

jann (39:04.868)
and buy her books and she's got a new book in the pipeline and you're working on another television show.

Chelsea Handler (39:08.895)
Yep. Oh, look at this guys. Oh my God, I'm sweating. Oh my God. What's going on? Oh my God. I must be a little.

Caitlin Green (39:13.814)
Oh! Ooh!

Sarah Burke (39:15.59)
Should we all, should we see what's going on? Okay, I'm heading.

Caitlin Green (39:17.386)
I probably am too, actually. No, I'm fine. Oh no, I am a bit.

jann (39:19.124)
And one more fun fact, one more fun fact, Chelsea Handler. I joined Rhea for 10 seconds. My friend, Danny Kind, who's a Canadian actress, talked me into it one day over a cup of tea as you do. Fucking filled Workin' Moms, the show. So I filled this thing out for five hours. Six months later, I get accepted into this thing that I'd forgotten about. And I'm like, oh my Christ. And so in one week, we're gonna be sending you

Sarah Burke (39:31.514)
From Working Moms, you know her.

jann (39:48.236)
the choices that Raya has made for you. And I was just like, okay, I'm gonna, all right. Ding, I was scared to open the app. You will laugh at this and don't ask me why. It was you. It was Drew Barrymore, Feist, the singer, and the fucking cop from Stranger Things. I love you so much, but I went, I deleted the app that afternoon because I thought this is...

Chelsea Handler (39:52.718)
Hehehe

jann (40:17.104)
insane. And that is fucking insane. And Leslie Fice, I texted her and she goes, oh, you outed me. Yeah. I said, well, I love you, Leslie. But anyway, so there's a fun fact. And now we're done.

Sarah Burke (40:18.534)
Imagine you guys dated?

Caitlin Green (40:20.423)
Hahaha!

Thanks for watching!

Chelsea Handler (40:33.171)
Okay, well I love that. I love it.

jann (40:35.724)
Thank you, and now we're truly done.

Caitlin Green (40:35.874)
Yeah. Title of episode is now going to be Jan's Raya match.

Chelsea Handler (40:39.435)
Yeah, and it's also called Raya, okay, Jen? Hey, hey!

jann (40:42.06)
But Raya, and it couldn't have been, and I was like over, I was very delighted. Oh God, she's gotta go. No. Well, enjoy the rest of your day and your people will look after this populating, but thanks from the bottom of our hearts. We appreciate it. Go keep kicking ass.

Caitlin Green (40:43.495)
Oh, crap.

Chelsea Handler (40:49.391)
Sorry, my dog just, yeah, no, my dog just had a bad reaction to... Okay.

Chelsea Handler (41:00.116)
Okay.

Okay, no problem. Sarah, you tell me what to do here.

Sarah Burke (41:05.534)
Okay, I'm gonna hit stop. It'll just.