The Evolution of Chelsea Handler Comedian Chelsea Handler talks about her new HBO Max stand-up special Chelsea Handler: Evolution. Then, the New York Times bestselling author is challenged to a game about authors portrayed in film.

The Evolution of Chelsea Handler

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Our final guest today is comedian and longtime host of "Chelsea Lately" on E! And her new HBO Max stand-up special was filmed outdoors following social distancing guidelines. And it's called "Chelsea Handler: Evolution." Chelsea Handler, hello.


EISENBERG: (Laughter) I love your new special. It's called "Chelsea Handler: Evolution." Now, this is your first stand-up special in six years. And you recorded it live in New Jersey, actually in front of a train station.

HANDLER: I did, in front of Liberty train station, which was an immigration train station from Ellis Island. People would get dropped off at Liberty's train station and then go, you know, be sent to wherever they were going throughout the country, wherever they were intending to live. So it had some meaning behind it, which was, of course, a draw for me.

EISENBERG: So when you're doing a special during the pandemic, what kind of safety measures did the audience have to go through to be able to sit there and enjoy the show?

HANDLER: Well, they had to get tested. Then they had to quarantine for five days. And then they had a test when they got to the show - rapid-response test. So - and then...


HANDLER: And then on top of that, there was social distancing. We were outside. And anyone who wanted to wear a mask was - you know, obviously could.

EISENBERG: And how - I mean, you know, it looks to me when I watch the special, and it sounds great, you know, and it feels very much like a live performance. But from your point of view as a stand-up, performing outside and the audio isn't the same and you're doing a special, like, how did it feel?

HANDLER: I mean, it was a real humbling experience. I was like, OK, don't get - whatever laughter and collective joy you're used to hearing, you better get un-used to it because there's social distancing, and there are people in masks. So you got to be really confident about your material.

EISENBERG: Yeah. You have to deliver it like you're killing all the time.

HANDLER: Yes. Yes. Exactly.

EISENBERG: Right. So in your 2019 show, which I loved, "Hello, Privilege. It's Me, Chelsea," that explores your relationship with white privilege - the work is never done, obviously. What have you learned recently about white privilege in this moment?

HANDLER: Oh, well, I mean, you know, you're learning about it all the time.


HANDLER: I think part of like - you know, if you want to work as being anti-racist instead of just against racism, you have to really kind of stick your neck out and say uncomfortable things. You know, one of the things that kept coming up in "Hello, Privilege. It's Me, Chelsea," that documentary I did, it was to examine the term white privilege and give it a clear meaning because I thought, oh, maybe that just means you went to Harvard or Yale, or you're from the Rockefeller or a Bush family. It means so much more than that. It means the privilege of walking into a grocery store and not being followed down the aisle. It means the privilege of being pulled over by the cops and arguing with them because you don't think you were doing anything wrong. It's the privilege of walking down the street and feeling safe, you know, versus walking down the street and feeling people being fearful of you.

It's all of these things. And so I made that film for - you know, my fan base is mostly white women. And I wanted to share with them my learning about that term and what does it really mean.

EISENBERG: Do you get backlash?

HANDLER: Yeah. I get a lot of backlash. I mean, I get, like - yeah, but who cares? I mean, that's not what this is about, you know? I mean, it's - I have - you know, I've been getting backlash my whole career, so at least I'm getting it for start standing up for what's right now, you know...


HANDLER: ...Instead of just talking about...

EISENBERG: The mindless.

HANDLER: ...You know, getting - right. Exactly. Thank you (laughter).

EISENBERG: Yeah. So we're talking to each other on Zoom, and I see a lot of books in your home. What are you reading right now?

HANDLER: Let me show you what I'm reading, actually.

EISENBERG: Yeah. Let's bring it over. I like the stack.

JONATHAN COULTON, BYLINE: Oh, I like that chair. That purple chair is fantastic, too.

HANDLER: Oh, thanks. OK, so these are the three books I'm reading right now. I just finished this book on Frederick Douglass, which is a - it's not an autobiography. It's by David Blight. It won the Pulitzer, I think - yeah. It's a biography, and this is about 800 long, so it took me about four months to read.


HANDLER: But I didn't know enough about Frederick Douglass, and I felt like I should, so I read that. This is "Caste" by Isabel Wilkerson, which is required reading for anyone. You both have to read this. It's incredible. It is brutal, but it's necessary. And then I'm reading this little - I always have these little - this is a Thomas Kempis, "The Inner Life." I always have, like, a George Orwell or, like, a little - like a, you know, an old writer that I can read because it's so prescient because you read this stuff, and it's very political usually. And they're basically describing a time 100 years ago, 200 years ago that we're still dealing with the same issues, whether it's race, whether it's politics, whether it's oppression, subjugation, you know? So it gives you a little - you know, in a certain respect, you're like, oh, my God, when are we ever going to solve any of these problems? But on the other hand, it's just - every book is a tool, you know? Every book is an educational tool. And I want to have the power in my brains to know what I'm talking about.

EISENBERG: Are you up for a ASK ME ANOTHER challenge?

HANDLER: Yeah, totally.

EISENBERG: OK, great. So because you've written six books and because you're an avid reader, we are going to give you a challenge about women writers portrayed on screen.


EISENBERG: OK. Yeah, so we're going to just play a clip from a television show or a movie, and all you have to do is tell us one of the following things - you can give us the name of the writer who is being portrayed, you can give us the name of the actor who is portraying her, or you can give us the title of the movie that the clip is from.

HANDLER: OK. OK, just - OK. I feel like I'm going to suck at this, but go for it.

EISENBERG: Any one of them.


EISENBERG: Also, we have loads of hints.

HANDLER: Great. Perfect.

EISENBERG: Here's your first clip.


JULIA ROBERTS: (As Elizabeth Gilbert) I'm going to Italy, and then I'm going to David's guru's ashram in India.

HANDLER: Julia Roberts.


ROBERTS: (As Elizabeth Gilbert) And I'm going to end the year in Bali. That's what I'm going to do.

HANDLER: I got all three. Elizabeth Gilbert wrote it. It's Julia Roberts, and the movie is "Eat Pray Love."

EISENBERG: Exactly. Exactly, exactly.

HANDLER: That was really easy, though, you guys.

EISENBERG: Right? Well, we got to start somewhere.

COULTON: It's the first one.

EISENBERG: We got to start somewhere. I like that already you were like, oh, good, I'm going to need lots of help. And now you're like, oh, this game...

COULTON: Oh, this game is so boring and easy.

EISENBERG: ...Is ridiculous.

HANDLER: Step it up.


COULTON: All right, here's another one. This clip is from a 2018 film starring an actor who usually appears in comedic roles.


MELISSA MCCARTHY: (As Lee Israel) Is everything I'm doing you think I'm copying? I'll have you know, I'm a better Dorothy Parker than Dorothy Parker.

UNIDENTIFIED ACTOR #2: (As character) I'll drink to that. Cheers.

HANDLER: Oh, Melissa McCarthy. Melissa McCarthy...

COULTON: That is correct - Melissa McCarthy.

HANDLER: Oh, she's so funny.

COULTON: She's brilliant.

HANDLER: Yeah, I remember this movie, but I don't remember the name of it. I'm not going to get it.

COULTON: It is called "Can You Ever Forgive Me?"

HANDLER: Oh, yeah.

COULTON: And it's about a writer named Lee Israel.

HANDLER: OK, good. Well, one out of three ain't bad, right?

COULTON: You got it. You still got it.

EISENBERG: Yeah. That's all you needed. That's all you needed.

COULTON: All right. This scene is from a 2017 movie starring Chadwick Boseman about the first Black Supreme Court justice. He's at a club with Langston Hughes when this author comes over to the table.


ROZONDA THOMAS: (As Zora Neale Hurston) Hi, how y'all doing? Langston Hughes.

JUSSIE SMOLLETT: (As Langston Hughes) Zora.

THOMAS: (As Zora Neale Hurston) And who is this?

MARK ST CYR: (As Langston's Boyfriend) I'm August. I've heard so much about you.

THOMAS: (As Zora Neale Hurston) Hmm. Well, that's funny because I haven't heard a thing about you. Huh, Langston?


HANDLER: OK, so the movie - "Thurgood Marshall" (ph) or "Marshall"?

COULTON: That's correct.


COULTON: That's the movie. You got it.


COULTON: And the writer was Zora Neale Hurston, played by Rozonda "Chilli" Thomas from TLC.

HANDLER: Oh, really? Oh, that's cool.


EISENBERG: Nice - right?

HANDLER: OK, cool. Yeah.

EISENBERG: All right, we've got two more for you. This 2005 film starred Philip Seymour Hoffman as the author of "In Cold Blood." And in this scene, he's on a train with his research assistant, when one of the crew members recognizes him.


KWESI AMEYAW: (As Porter) Hope you won't mind me saying, but I thought your last book was even better than the first.

PHILIP SEYMOUR HOFFMAN: (As Truman Capote) Thank you.

AMEYAW: (As Porter) Just when you think they've gotten as good as they can get.

HOFFMAN: (As Truman Capote) Thank you very much.

AMEYAW: (As Porter) Ma'am.

HOFFMAN: (As Truman Capote) What?

CATHERINE KEENER: (As Nelle Harper Lee) You paid him to say that. You paid him to say that.

HOFFMAN: (As Truman Capote) How did you know?

KEENER: (As Nelle Harper Lee) Just when you think they've gotten as good as they can get?

HOFFMAN: (As Truman Capote) I thought that was a good line.


HANDLER: What was that guy's name?


COULTON: Mmm hmm. Mmm hmm.

HANDLER: Truman Capote.

EISENBERG: (Laughter).

COULTON: Truman Capote, yes.


HANDLER: I believe there were two movies. I believe there were two movies about him at that time.

COULTON: (Laughter).

EISENBERG: That's right. Perfect. Oh, my goodness. And his research assistant, of course, wrote a little book called "To Kill A Mockingbird"...


EISENBERG: ...Which I believe is...

HANDLER: Harper E. Lee (ph). I know the - I know the author of that.

EISENBERG: That's right. Yeah. Always be nice to your assistant because they might end up writing...

COULTON: Because you never know.

EISENBERG: ..."To Kill A Mockingbird."

HANDLER: Oh yeah, I know.

COULTON: That's right.

HANDLER: Oh, my God. I know. That must have been before nondisclosure agreements.


COULTON: Presumably, yes.

HANDLER: People weren't...

COULTON: All right.

HANDLER: ...Thinking on their toes back then.

EISENBERG: They were like, wait a second.

COULTON: (Laughter) All right. This is the last clue.


COULTON: This 2009 film was about Julia Child, played by Meryl Streep, and a blogger who decides to make all of her recipes.


AMY ADAMS: (As Julie Powell) Yesterday was Tuesday, August 13, 2002. Day 1 - 364 days to go. I cooked artichokes with hollandaise sauce, which is melted butter that's been whipped into a frenzy with egg yolks until it's died and gone to heaven.

HANDLER: That's Amy. And I (laughter) - she's a friend of mine, but I can't think of her last name.

COULTON: (Laughter).

HANDLER: Amy Adams. Amy Adams.

COULTON: Amy Adams is correct. Yes.



COULTON: I love that. I just know her by Amy. I don't even think of her last name.


HANDLER: Yeah, exactly.

COULTON: She's my pal. She's my pal.


COULTON: That is correct. Do you remember the name of the movie?

HANDLER: Was it not called "Julia" (ph)? No.

COULTON: It was called "Julie & Julia."

HANDLER: Oh, I see. Well, that sounds like a trick question if you ask me.


EISENBERG: Well, the real - it was a trick question because we all know the true star of that film was the butter. The stick of butter was really the...

HANDLER: (Laughter) Right.

COULTON: Oh, absolutely.

HANDLER: By the way, if you put a stick of butter in anything - exactly - it's going to come out...

COULTON: It makes it delicious.

EISENBERG: (Laughter) It's perfect. It's perfect.

COULTON: Julia Child knew that. And, of course, the writer was the blogger and - who wrote a book about that - it's Julie - Julie Powell is her name.

HANDLER: OK, copy that. Got it.

EISENBERG: You did amazing. You got all of them correct.


EISENBERG: All of them.

HANDLER: Oh, my goodness, you guys.


HANDLER: Oh, my God. I'm a bona fide reader, movie-watcher.

COULTON: That's right.

EISENBERG: Thank you so much, Chelsea. It was an absolute honor to meet you and play some games with you.

HANDLER: Oh, that's nice. That was fun, you guys. It was really fun. Nice to see you.

COULTON: You too, thank you.

EISENBERG: Nice to see you too, thanks.


EISENBERG: Chelsea Handler's new memoir is called "Life Will Be The Death Of Me." And her stand-up special, "Chelsea Handler: Evolution," is on HBO Max.


EISENBERG: That's our show. ASK ME ANOTHER's house musician is Jonathan Coulton.

COULTON: Hey, my name anagrams to thou jolt a cannon.

EISENBERG: Our puzzles were written by our staff along with Scott Ross and senior writer Karen Lurie, with additional material by Cara Weinberger and Emily Winter. ASK ME ANOTHER is produced by Travis Larchuk, Nancy Saechao, James Farber, Rommel Wood and our intern Sam Yellowhorse Kesler. Our senior supervising producer is Rachel Neel. And our boss' bosses are Steve Nelson and Anya Grundmann. Thanks to our production partner, WNYC.

I'm her ripe begonias.

COULTON: Ophira Eisenberg.



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