- [Announcer] This program was made possible by contributions to your PBS station from viewers like you.

Thank you.

- The first thing I look for when I read a script is does the story move me?

The only failure is if you move an audience to nothing, to boredom.

If they are indifferent about what they just experienced, whether it's a painting or a recital or a singer or a dancer or a play, if they are, I feel nothing throughout then we failed.

(upbeat music) - Hi everyone, this is "Beyond the Canvas" from "PBS NewsHour."

I'm Amna Nawaz.

In this episode we examine how success is born from a combination of deep ambition, a little bit of luck, and timing.

You'll hear from award-winning artist, Lin-Manuel Miranda; YouTube star, Lilly Singh; up and coming playwright, Jeremy O. Harris; and as you just heard, actor Brian Cranston.

And one of the many themes is breaking boundaries.

All of our featured artists reveal how their fame came about through consistently defying expectations and speaking their truth.

You may have seen these artists before on the "PBS NewsHour," but tonight you'll meet them on a new canvas, and maybe experience their work through a different lens.

That's right here on "Beyond the Canvas."

- What I truly love about this, and when I talk to audiences about anything I've done or any other movie or stage piece is that the audience is always right.

However you felt, however you reacted to something, is always right.

That's how you felt.

And it's remarkable how you can sit next to someone and watch a movie, I could be weeping, and they're like, eh.

It's like really?

And it's like, yeah, it missed me.

Actors come to town to New York or Los Angeles or London.

And they say, you know, I'm gonna give it a shot.

I'm gonna give it a year and see if I can become successful.

And to those, I wanna say, I could save you a year of your time.

If you think that this is something that you can carve out some arbitrary amount of time to achieve certain things, this is not for you.

This is a lifetime.

When you first start out as an actor your answer to any question is yes.

Do you want to?

Yes, I wanna do that.

I started out in 1979 doing background work as an extra, angry mob, drunken frat boy, reckless driver.

And then when you first get that break where you actually have a name.

Steve, wow, I actually have a name.

I'm Steve.

That you feel like you've progressed to some degree.

There is no career that has ever been achieved in entertainment, I truly believe this, without a healthy dose of luck.

Someone said, okay, kid, I'll read your script, or all right, you wanna audition?

Come in, do it right now.

And then you gotta be ready.

Celebrity is a byproduct of what I do and what I like to do.

It's not what I was after.

I was a working actor.

Things were fine.

I was paying my bills, leading a very middle class economic life.

And then I got a lucky break at age 40 and was cast in "Malcolm in the Middle."

At 50, I got an even bigger break when I was cast as Walter White on "Breaking Bad."

That was my trajectory.

It came when it was supposed to come.

And that's the interesting thing about luck.

It doesn't work on your timetable.

It works on its own.

My name is Bryan Cranston, and this is my brief, but spectacular take on being an actor.

- Like Cranston, creative talent Lin-Manuel Miranda knows a little something about timing.

He's responsible for finally bringing treasury secretary Alexander Hamilton into the limelight, 200 years after his death.

For Miranda, it felt essential to use a diverse cast and premiere the first hip hop musical on Broadway.

Coming up next, we look back at his Broadway debut when he sat down with Jeffrey Brown to talk about finding the courage, to tell an old story in a new way.

♪ I'm past patiently waitin' ♪ ♪ I'm passionately smashin' ♪ every expectation ♪ ♪ Every action's an act of ♪ creation ♪ - [Jeffrey] It's the coolest American history lesson you're likely to get.

♪ And I am not throwin' away my ♪ shot ♪ And the hottest ticket on Broadway.

"Hamilton," a kind of hip hop musical, tells of Alexander Hamilton, immigrant and vitreous young rebel, page of George Washington, a founding father, who arguably never got the recognition he deserved.

- I'm actually working on a hip hop album.

It's a concept album about the life of someone I think embodies hip hop, Treasury Secretary Alexander Hamilton.

(audience laughing) You laugh.

- [Jeffrey] Hamilton's creator and star Lin-Manuel Miranda performed an early version of one of the play's songs at the White House in 2009.

♪ How does a bastard orphan ♪ son of a whore and a Scotsman ♪ ♪ Dropped in the middle ♪ of a forgotten spot ♪ ♪ In the Caribbean by ♪ providence impoverished ♪ ♪ In squalor grow up to ♪ be a hero and a scholar ♪ - When we talked recently, he told me how Hamilton's life came to be about so much more.

- The joy of discovery of, oh, if I tell Hamilton's story, I actually tell the story of the forming of our country.

That was a joyous experience.

And I think honestly, that's the secret sauce in the score.

I was learning this stuff as I was researching it to write the show.

I knew the broad outlines that everyone knows.

He was on the 10 and he died in a duel.

That's pretty much all anyone knows about Alexander Hamilton.

- But were you thinking from the beginning that there, that this larger story was what would emerge?

- Through his life.

I knew that reading, reading Ron Chernow's biography of his life was like a Dickens novel.

Such humble beginnings to such incredible heights, and such incredible incident throughout that I always tell people, I feel like a mosquito that hit an artery.

Like there's so much here.

How am I gonna get it all?

- Story-wise, there so much there.

- Absolutely.

What I'm always on the hunt for when I'm writing a song are details.

Our mantra is the political always has to be personal.

So if you're gonna write a song about the compromise that led to Hamilton trading his votes in the debt plan for the capital of the U.S. being down here in the newly formed D.C., well, that's easy to say in a sentence, but let's tell it from the perspective of Aaron Burr, who wasn't in the room, and is desperately wants to be in that room.

And suddenly we can get away with anything because we've got a dramatic tension.

♪ I wanna be in the ♪ room where it happened ♪ - And the language, the rhythms of hip hop.

- It's the best form for "Hamilton."

And when you extrapolate from him, it's a wonderful language for our revolution.

We need a revolutionary language to describe a revolution.

This was a war of ideas in a sense.

We needed not only great fighters, but great thinkers.

And so hip hop is uniquely suited to that.

'Cause we get more language per measure than any other musical form.

- What about the casting of the founding fathers as Latino, as black?

Was that, is that, is that important part of this to you?

- I think so.

I think one of our overarching goals with this show is, with any show is, you wanna eliminate any distance between your audience and your story.

And so let's not pretend this is a textbook.

Let's make the founders of our country look like what our country looks like now.

- So it's not a costume epic-- - Correct, correct.

And this is what our country looks like now.

It looks like, we are every shade and every color.

And it also comes organically out of the music.

This is hip hop and R and B music.

These are the best people to sing this type of music.

(audience cheering) - [Jeffrey] These days, Miranda is, himself, a new kind of rockstar feted all over.

We joined him in Washington as he received an Ingenuity Award from the Smithsonian Institution and gave a talk to an adoring audience.

I asked him about the use of the word ingenuity to describe his work, and that brought on a characteristic riff on how he develops his own wordplay.

- 'Cause I remembered there's a lyric in our show where Lafayette says ingenuitive and fluid in French.

And I remember having a fight, not having a fight, but having a debate with my collaborators, 'cause one of them was like, well, that's not a word, ingenuitive.

And I was like, I think it is.

And then we were split two to two, whether ingenuitive was a word, and we looked it up and it is an archaic conjugation of ingenuity.

And I was right.

And I don't know why I knew that word.

So, and other people didn't, but.

- And therefore you use it.

- And therefore we use it, yeah.

- But you can make up words if you want, can't you?

- Well, Shakespeare did it, it worked out pretty great for him.

- So writing musicals, entertaining people, telling stories, and now filling in large gaps in American history.

Is there a hierarchy of that for you?

What's most important to you?

- The most important thing for me, honestly, is meeting those expectations every night.

We are not film actors in that show.

It's not like you get it once on camera in the can and we're done.

We're chefs and we have to make that experience happen for the audience that I'm gonna see tonight after I get on the plane, for the same audience that, for a different audience that I saw last night.

I saw where you said you think to yourself, what's the thing that's not in the world that should be in the world?

That's a big idea, right?

- Yeah.

- I mean, you feel that, like what's missing in our world?

- Absolutely, I mean, and it goes back to, I hope that what I can contribute is something that hasn't been seen before.

"In the Heights" very much came out of me wanting a career in musical theater, but there's only about three great roles for Latino men in musical theater.

You're Bernardo, you're Paul in "A Chorus Line," or if you can really sing, you're "Man of La Mancha."

I can't sing well enough to be the "Man of La Mancha."

- [Jeffrey] So you did two out of three.

- So I wrote something that had so many parts for Latinos because I knew there was a void there.

I knew it because I was going into that world and I was scared.

- But it's also a big idea to think that you can fill a vacuum.

- I think that's what we do as artists.

It's, what's the thing that only I can contribute.

It's not about the confidence to like, hello world, here's this idea that never existed.

It's this is my brain.

And unless I express it, it's only gonna stay in my brain.

It's more about personal expression than imposing your will on the world.

It's more about if I don't get this idea out of my head and onto paper it dies with me.

♪ I'm not throwin' away my ♪ ♪ Not throwin' away my shot ♪ - Breaking out of theater norms is part of what made Miranda's "Hamilton," a worldwide sensation, and comedian Lilly Singh knows all about breaking barriers in the entertainment industry.

Singh began her career in 2010 on YouTube, where she created hilarious skits about growing up in an Indian family in Canada.

Now she's one of the lone female voices on late night network television.

She spoke with me in 2019 about not letting fear get in the way of forging new ground.

I visited Singh on her Los Angeles set to get a behind the scenes look before her big debut.

- The 10 stages of diet grief, dun dun dun dun dun.

- [Amna] She's one of YouTube's biggest success stories ever.

- What up everyone, it's your girl, Superwoman.

No.

- Lilly Singh, AKA Superwoman, first dipped a toe into internet waters 10 years ago with basic video blog.

- So when it comes to our boyfriends, we want all the attention we can get, which makes us, okay, a little bit needy.

- [Amna] But she quickly dove in deeper, developing her comedic skill.

- No girl, I am wearing flats, ain't nobody got time for heels tonight.

Wait, what?

♪ Car go splash, give you ♪ whiplash ♪ - [Amna] And over the years upping her production game.

♪ Kitty go meow ♪ ♪ Spill a drink ♪ ♪ Use a paper towel ♪ - [Amna] Translating both into 14 million subscribers and over three billion video views.

♪ The president wanna build ♪ a wall 'cause I'm brown ♪ ♪ I'm like Chris Jericho ♪ I break the wall down ♪ - [Amna] She's now going where no YouTuber has gone before, network television.

Tonight she'll make her debut on NBC as host of "A Little Late With Lilly Singh," taking over the late night time slot from Carson Daly.

- Welcome to the show.

- [Amna] Singh made the announcement in March, welcomed by her fellow NBC late night, hosts, Jimmy Fallon and Seth Meyers.

- Indian Canadian woman, also (voices muffled).

- Come on man, breaking records.

- So I'm super honored and humbled.

- She built her fame by standing out online and in her new role, Singh will definitely stand apart.

When your show premieres, you are going to be the only woman on the major networks in late night in a sea of white male hosts.

How are you thinking about that?

- Honestly, it's exciting and nerve wracking at the same time.

I mean, it's a huge honor.

I'm so humbled to be part of creating that path because, let's be real, I wouldn't be here without the women that helped pave the path before me.

I think that's, for the same reason, it's so important for me to bring that authentic point of view.

- [Amna] She'll also be the only woman of color on late night television, and the first LGBTQ host of any network late night show, ever.

Singh came out as bisexual to her family last year and to her fans just six months ago.

- It's been tough.

But end of the day, I always think there's two ways that you can go.

You can go the route that is scared, I'm scared, or you can go the route of I'm going to lead with love.

And I think the route of leading with love is even though this is scary, I'm going to share this about myself because it will help people.

And all I wanna do is encourage more people in our community, especially our South Asian community, to be like, even if something is scary and you're not supposed to talk about it, talk about it.

Talk about it.

Lead with love.

- That lesson was years in the making, tracing back to 2010 when Singh posted her first video on YouTube with no clear career plans, struggling with depression, and living in her parents' suburban Toronto home.

But right away, Singh says, she knew this was her path.

What was that conversation with your parents like?

Like what is the line you delivered?

- It was like, hey, (clearing throat) I don't wanna go to grad school.

I would like to make videos on YouTube.

- Sounds reasonable.

- Yeah, they had a lot of questions, but I think in their mind, they're like, this is a phase.

She's gonna grow out of it.

Next year she's gonna do these essays, get into graduate school.

I do not think they were expecting me to make a career out of this.

I don't think anyone was, to be fair.

♪ I got, I got, I got ♪ - [Amna] Branding herself as Superwoman, Singh set herself apart on a crowded internet by leaning into her view of the world.

♪ I got thymine, guanine, ♪ cytosine, adenine ♪ ♪ inside my DNA.

♪ - Why the bloody hell did you wake up so late, huh?

Good morning to you, too, mom.

- [Amna] Posting campy impersonations of her parents, and delivering a steady stream of observational humor in her signature over the top style.

- Oh sweet baby Jesus, is that double cheese?

- [Amna] As her followers and her fame grew, Singh's reach extended far beyond the internet.

In just under 10 years she ascended into entertainment's upper echelon, collaborating with Hollywood royalty, like The Rock; pop culture stars like Selena Gomez; even interviewing then First Lady, Michelle Obama.

- No, you hang up.

- [Amna] The Lilly Singh empire has now unfurled across media platforms.

In 2017, she published a self-help book called, "How to Be a Bawse," or as she would say it.

- "How to Be a Bawse."

- [Amna] The book, went on to become a New York Times Bestseller.

Her world tours sold out in dozens of countries, and her journey so far has even been documented in a 2016 film, "A Trip to Unicorn Island."

For her next chapter, Singh has brought along the team from some of her biggest viral hits, hoping they can create the same success for NBC.

- Social media people are mine.

The editor is mine.

Got my desk out here.

- [Amna] Equally important, she says, is the history she's carrying forward.

In 1986, Joan Rivers became the first woman given a shot at the late night chair, but she failed to gain traction and was quickly taken off the air.

It took decades before another woman was given a chance.

And since then, no woman has made it past a single season in late night on any major network.

- And so it's a lot to deal with, but I always just remind myself that it's part of chipping away that path.

And so regardless of what the outcome is, if I'm being super candid with you, it's kind of not gonna matter because it's gonna help continue pave that path.

And that's what my priority is.

- You're saying regardless of how this goes, the fact that you are here.

- I mean, we want it to go well, there's no doubt, we want it to go well.

But I'm saying is my actual presence and everyone else being a part of this is already gonna contribute to paving that path - [Amna] In some ways, Singh is uniquely qualified to succeed in the new world of late night, one in which hosts are scrambling to turn television segments into internet sensations.

- When I'm sitting with my writers and we're going through the show format, I think great, that's a great show.

And I think by nature, my brain automatically goes, that's gonna be the YouTube part of it.

And this is what the title is gonna be.

And that's gonna be great.

So it's just of just-- - You can just see that now.

- It's already built in, like I'm already sitting with my writers being like, perfect, and we'll call it this and we'll frame the question like this.

It'll be done.

So I think it's just a different way of thinking.

It's about thinking about two formats rather than just one.

Come on.

We're out here makin' statements.

Statements on statements out here.

I love it.

- [Amna] When her show premieres tonight, Singh says she knows she'll be speaking to a largely new television audience, one she won't have much time to win over.

- I wanna go through and be like, this is my point of view.

This is what I'm going through.

These are my thoughts and feelings.

This is the person I am.

This is the person I want you to get to know, not just talk show host, but like I want you to get to know Lilly.

- Singh's positive message on embracing our own identities is a powerful theme among a lot of younger entertainers.

Another newcomer making waves is playwright, Jeremy O. Harris.

His critically acclaimed "Slave Play," debuted on Broadway in 2019.

The play explores the negotiation of sex, race, and power among three interracial couples.

Raised by a single mother in rural Virginia, Harris was used to being the only person of color in his class.

He spoke to my colleague, Steve Goldbloom, about how that experience shaped his identity and his writing.

- I'm a very confident writer.

- That's good.

- Yeah.

- Does that translate into other areas of your life?

- Confidence helped me feel like I belonged everywhere.

- And what about relationships?

- Oh, with like guys?

- Yeah.

- Horrible.

- So the confidence.

- Yeah.

No, I mean, I can get, I can get people, but then I think I become tiresome for them.

I mean I date people who are also very ambitious, so it tends to be a thing where it's like, who's gonna be the star of this week, and it's like, I'm gonna be a star.

- What did it feel like to grow up as one of the only people of color in a white private school?

What toll did that take on your identity?

- I think I have the proper temperament for that sort of navigation.

This teacher told my mom when I was in eighth grade, like Jeremy is just a sponge.

He soaks it all up.

That comes as good and bad.

If anything, the toll that it took on me was like, there was a distance I had between me and black and brown people.

Internalized racism is something that happens in a space like that so easily, that that's the biggest price I paid was that I had to do the work of unlearning so many toxic and violent things that were embedded in me from kindergarten and on about like what my worth was in comparison to other people, and specifically other people of color, because a lot of times we were told, people think they're complimenting you by positioning you outside of some marker of identity that they find untowards.

They're like, oh my god, Jeremy, like, you know, you're so gay, but you never feel gay when you're just like reading your plays or, like Jeremy, you're not that kind of black person.

And all those things sort of nick away at your own identity and your own relationship to other people of color and other queer people.

Now that I'm in a position to regurgitate and reframe, I can use all of that in order to create these new psychic spaces to make people see themselves in ways they probably wouldn't even if they looked in a mirror.

I decided to go to drama school after my mother had worked very hard to send me to private school.

When I found out that there was a school where they accepted 52 kids and only 26 got to stay at the end.

I was like, this sounds great.

It sounds exactly like every reality show I love.

So I'm gonna go there.

I felt very confident in my section.

And then I was immediately cut (laughing).

And it was funny 'cause everyone had these lists of people that are like this person's gonna stay, this person's gonna go, and I was on most people's stay list, but one friend had put me on her, Jeremy's getting cut list.

And I was like, why would she do that?

And she was like, because Jeremy, you're too weird.

You're just too weird.

I don't see it for you.

And I was like, oh, okay.

We're auditioning for "All That."

- "All That."

- My too weirdness.

It used to be the thing that opened every door for me.

But I realized that in a world of drama or in a professional theater, it could be kind of limiting because I'm not every type.

My hair was down to here.

I'm like six foot four, lanky, obviously gay, and there was literally no one on TV or film or in theater that looked like me, so I can see why they could be like, I dunno, maybe we're doing this kid a favor by not telling him he could have a career as an actor.

So I decided to prove them wrong.

Being 19 and stupid and so angry and ambitious, I'm angry about this cut and ambitious to prove everyone wrong.

So it became the fuel to a fire that gave me a great career and got me cast a lot more than a lot of people who had graduated the year previous to that.

- Jeremy, describe for me the moment when you saw or read a piece of art that you felt like mirrored your experience.

- There was this book in high school.

One significant play from each moment of theater in the western canon.

And I don't even know why this play, but I love the title "Machinal."

And in that same book was Suzan-Lori Parks' "In the Blood."

It was something about this confluence of both these things about these women who lived, whose bodies and minds were under attack by society, where I felt seen.

- [Steve] Tell me about what it felt like to learn that Robert O'Hara was directing the play.

Well, I mean, that's a piece of work, you asked at one point, when was a place I felt seen, "Insurrection: Holding History," was a place I felt so completely seen.

And I think it's so rare that a young person, especially a young black or queer person, gets to work with an idol.

- A lot of people are writing about you.

What does it feel like when people start saying new voice of a generation, missing voice?

- What excites me about these things is that they open new potentials for me.

There's potentials for me to help also, say, if you think my voice is so cool, a voice I think is cool is Alicia Harris, a voice I think is cool Celine Song, a voice I think is cool is Will Arbery.

That's a great thing.

And their gets to be a lot of new voices.

You know what I mean?

- What is your relationship with the audience and how much are you looking to challenge the audience or make the audience squirm and uncomfortable?

- Because right now we have a theatrical space that is made up so predominantly by one class of people, I would like to create, to do the work of making those people rethink coming into that space so that perhaps new people might feel invited in.

For a long time I've been in spaces of discomfort and had to thrive within those spaces and have seen, and have seen how those spaces have fallen apart when I've negotiated my own discomfort in relationship to their comfort.

So the minute I bring up the fact that it's weird being the only black person in this private school for five years, the minute I started thinking about those things, the minute I think that when I have the keys to the car, I wanna drive it as fast as I can.

(relaxed music) - And there's no doubt that Jeremy O. Harris's work will continue to break new ground.

Now all of the artists we featured are still paving the way toward a more genuine and diverse way of storytelling.

You can see more from them on our website, pbs.org/newshour/canvas, and tune in to the "PBS NewsHour" each night for even more "Canvas" arts and culture reporting.

Coming up on "Beyond the Canvas," crossover, country music star, Kacey Musgraves.

- With this record, I was like, I want to reach beyond country music, and not leave country music behind, I wanna take it with me.

- [Amna] The legendary Joan Baez.

- That was a special period of time.

And one of the problems now is people look back and they want that now, and you can't have it.

I mean, you can't have a repeat.

Something new has to emerge.

I'm Amna Nawaz.

For all of us at the "PBS NewsHour," thanks for joining me here on "Beyond the Canvas."

We'll see ya soon.

♪ I'm past patiently waitin' ♪ ♪ I'm passionately smashin' ♪ every expectation ♪ ♪ Every action's an act of ♪ creation ♪ ♪ I'm laughin' in the face ♪ of casualties and sorrow ♪ ♪ For the first time I'm ♪ thinkin' past tomorrow ♪ ♪ And I am not throwin' away my ♪ shot ♪ ♪ I am not throwin' away ♪ my shot ♪ ♪ Hey yo I'm just like my ♪ country ♪ ♪ I'm young scrappy and hungry ♪ ♪ And I'm not throwin' away my ♪ shot ♪ ♪ We're gonna rise up ♪ ♪ Time to take a shot ♪ ♪ We're gonna rise up ♪ ♪ Time to take a shot ♪ ♪ We're gonna rise up ♪ - [Announcer] This program was made possible by contributions to your PBS station from viewers like you.

Thank you.