Chelsea Handler Dishes on Her New Book, Her Milestone Birthday & Her Comedy Special

To say that Chelsea Handler is the Jill of all trades feels like a massive understatement. The New York Times bestselling author, podcaster, stand-up comedian, actress and advocate has been working hard since the age of 10—when she made a small fortune from selling spiked lemonade. Now, the 49-year-old star is preparing to ring in her milestone birthday with the release of her seventh book, I'll Have What She's Having.

I got to sit down with Handler to discuss the new collection of essays, which detail her journey to becoming the bold and carefree woman we all know and love. And in case you're wondering—yes, that clever title is definitely a reference to the famous orgasm scene in When Harry Met Sally.

She told me, "My editor actually came up with the title when she pitched it to me. I'm like, 'I'm not naming a book I'll Have What She's Having. Like, how can I self-proclaim that?' And she's like, 'It's a feeling you get when you read the book. Everyone's gonna feel it."

Keep reading for all the details on her memoir, her birthday plans, her upcoming Netflix special and more.

PureWow: First off, congrats on your seventh book. What inspired you to write this memoir?

Chelsea Handler: Well, the book I originally tried to write [was about] falling in love, in a very public way, with Jo Koy. I was approached about writing a book about falling in love, since it was an unexpected, public display of affection, and everyone just seemed to really be rooting for us. So I was approached at that time to write a book about falling in love, but then Jo Koy and I broke up. And then I thought, 'OK, well, maybe I could write a book about actually breaking up in a more graceful way than I ever had previously.' And then I thought, 'No, I don't really want to write a breakup book.' And then, as I just allowed it to sit there in the back of my head without any real pressure to write a book.

It kind of dawned on me that I might want to write a book about all of the things that make up who you are. You know, all of the things that kind of grow you into the adult version of yourself, and the slip-ups and the wins and the progression of maturity and the progression of getting to know yourself and living in a loud, brave way, are just all sentiments. I just wanted to get out there. I'm like, 'Oh, everybody needs a little injection of this.'

PW: What was the writing process like for you? How did that compare to writing your stand-up routines?

CH: It was very sporadic because I had an idea of what I wanted. With books, it's a very different medium. You know, I do stand up, I do podcasts, I do television, I do all of those things, but books is a very different medium in terms of, I've never written an outline for any book, so if someone asks me to summarize a book, it could be one thing one day and a different thing on Wednesday. I don't have that kind of clear, linear thinking. I'm a creative, so I'm a little bit all over the place.

I have no creative structure. It's very loose. And when I'm in the mood to write, I write. I have only one collaborator until it's absolutely finished, really, and then I show it to more people, but my one collaborator, being the editor, and just bouncing stuff off of her. It wasn't like any books I had ever set out to write, where I sold the book. They kind of came my way and approached me based on a circumstance that didn't end up being true. So the kind of crux of the book, that ended up being part of my story, that love affair with Jo Koy, but that isn't my story.

PW: What part of the book did you enjoy writing the most? What stood out for you?

CH: I think just writing the letter to myself as a little child, instead of the adult version of me, because I've always really been in touch with that version of me, and I think that's everyone's truest version of themselves, is them as a child before you're unbesmirched and you haven't had the residue of living what life entails, you are really the true essence of who you are. And we kind of lose track of that as we grow up and go through life, we lose track of our child version, and in many ways, only hold on to the unhealthy parts of that child. So I just like the idea of growing up into yourself, kind of having a plan for the person you want to be, and then checking in and making sure you're on the right track to getting there.

PW: Circling back to your milestone birthday, how are you planning to celebrate?

CH: Well, we're all flying to an undisclosed location to film my 50th birthday ski video, and it's turned into quite a production. So we're all getting on a plane, flying there. And Monday is our big shoot day, and it's turned into quite a massive shoot. So I'm just hoping everything works in our favor, and that it's a home run.

And then what else do I have? I'm gonna have a birthday party up here in Whistler, and then my book comes out on the 25th in New York City. So I'll have a party in New York City. And then I think I'll just keep having parties. I have book parties lined up throughout the country, then I'll probably have a party in LA and just celebrate myself this year. It's been a really long time, and a lot of success and a lot of highs, and I want to spend the year writing notes to all of the people that have made such an impact in my life, and being like, 'Thank you for sticking around.'

PW: You're aging so gracefully and I love that you embrace the process. What advice would you give to women who don't share this sentiment, or who worry about getting older?

CH: It's just better to have a good attitude than a shitty one. It's gonna keep you younger. You know, being happy, it does. There's nothing we can do about aging. You should be grateful to be alive, like, that's the last thing we should be complaining about. So I just don't have room for it. It's not an option. I would never, ever complain about aging.

PW: I read that you're making history as the first female comedian to have a Las Vegas residency. How does that feel?

CH: It's great. I mean, Vegas is Vegas, and I have a very like, short-term relationship with Vegas. I can only spend 24 hours there, so this residency is, like, once a month for the next few years, I couldn't think of a better schedule for myself, and I make the most of it. I bring up as many friends every show, like I have a group of friends that wants to come, and so we make a thing of it. We make a night of it and go to a fun restaurant, and then we go gamble. I'm so lucky when I gamble.

PW: Your podcast, Dear Chelsea, is also a big hit. What's the most rewarding part of that?

CH: My podcast is really fun, because I get to give real people advice, which takes up the other part of my time, Dear Chelsea. That's been a really fun, surprising success, because I just kind of did what I wanted to do without thinking of the masses, and people really came to it. Giving out advice is so my jam. I love getting involved in people's interpersonal affairs. Like, it's my favorite thing. So the fact that people call in, and what better person to get advice from than someone who has no skin in your game, who doesn't know your situation? I have nothing to gain from lying or giving them bad advice. So that's been a real treat. And just overall, I feel like, again, your attitude just makes you a better player at the game, it impacts everything in a positive way.