"We are on the precipice of both a renaissance – an awakening and a greatness – but also a much darker time as well. And it’s going to be incumbent upon us to determine where that goes.”

Don Cheadle said those words to me in the final week of February. I’m writing these ones in the dying days of April. 

It’s fair to say a lot has changed over the intervening two months, and a lot more will have done so by the time you read this interview. Yet the above sentiment rings truer than ever. 

Indeed, the only question is whether we are still teetering on the precipice or have plunged headlong into the abyss. That darkness, is it broken or gathering?

[SM: Now the interview is published in June, we can safely say: yes, a lot more has changed. In light of the George Floyd murder, the Black Lives Matter protests and the increasing despotism of an increasingly beleaguered Donald Trump, the moment of truth may now be upon us. The world is blinking itself awake.] 

Covid-19 will likely be the dominant force of 2020, and possibly many years to come, but as an activist Cheadle recognises there are struggles on many fronts: climate change, LGBTQ rights, #MeToo, diversity mandates, and the upcoming American election. 

Regarding the latter, Cheadle’s disdain for the incumbent President is nigh-on total. When I ask his opinion on Trump’s first term, he shoots me a look that says, ‘you really want me to go there?’ and then proceeds to ‘Go There’: skewering his namesake on everything from race relations to the justice system.

Cheadle’s case for the prosecution is passionate, informed, and very funny.

He’d have made a good lawyer, Cheadle, and a great stand-up comic. He tells a hell of an anecdote – look out for the one about the ‘straws’ – and can switch seamlessly from philosophical musing to social observation to off-the-cuff wisecrack, often in the course of a single sentence.

Cheadle is unique in being recruited by both Danny Ocean and the Avengers, the two glitziest star vehicles of 21st-century Hollywood.

It’s easy to understand his popularity among his fellow actors: Cheadle is unique in being recruited by both Danny Ocean and the Avengers, the two glitziest star vehicles of 21st-century Hollywood.

It’s a far cry from the 1980s, when a young Cheadle and his friends from drama school would attend the same auditions, often for the same role, hoping one of them would get booked so the rest could get by.

Of course, you don’t need us to tell you that over the past 35 years, Cheadle has established himself as one of America’s finest living actors, with a resume as diverse as any in the business: Devil in a Blue Dress, Rosewood, Boogie Nights, Hotel Rwanda, Crash, The Guard, Flight and the upcoming Space Jam 2.

Oh, and a recurring role in the highest-grossing film franchise of all time, of course.

Yet, it’s his recent TV roles that might hold a particular affinity for Square Mile readers.

Firstly, his performance in management consultant comedy House of Lies, a show far more cool and funny than the ‘management consultant comedy’ part of the description might suggest. (Cheadle bagged a Golden Globe.)

And latterly in Black Monday, another acclaimed comedy, this time set in 1980s Wall Street: a gleaming corridor of drugs, depravity and dodgy deals. (A throwback, a total throwback. Different worlds.)

Originally, Cheadle was due to be our March front cover to coincide with the second season of Black Monday. Then – well, you know what happened next.

Yet Black Monday also took a pause, and serendipitously – not often that word gets an airing in 2020 – the final episodes of the season will run at the end of June. Don’t you love it when a globally devastating pandemic comes together? (Does that make it a ‘plandemic’? -Ed)

Plenty more must come together before we attain the ‘greatness’ Cheadle alluded to – starting with the defenestration of Trump.

Then there’s that other C-word to deal with, oh, and the small matter of saving the planet.

Cheadle certainly won’t give up the fight, anymore than he’ll stop entertaining us on screens big and small.

If you hadn’t realised, the man’s a bit of a Don.

View on Instagram

Your character in Black Monday, Mo Monroe, is a bit of a scoundrel, a fast talker. Is there anyone you had in mind when creating the character?

This is not anyone specific, but there’s a lot of that energy that you get from the guys of that time and, of course, cocaine always helps to fuel that energy.

You read about these guys who are just flying by the seat of their pants at a time when regulations weren’t what they are now, and people were just freewheeling it. It was very much the Wild Wild West.

So, to have a comedy where it’s not all the way to farce but we’re definitely pushing reality, these are characters that are pushed, and that we’re taking to another level.

We’re not really trying to do any neorealism. It’s a comedy and it’s maximised as a comedy.

So I don’t know that there are any guys that I would point to out there that I would go, “That’s like Mo.” There may be, but a lot of those guys are probably in jail.

Did you go into any trading firms on Wall Street? It’s probably quite different now than it was back in the 1980s.

It’s very different now. I’ve been to them but, again, our due north is always the script.

One of our creator’s father was a trader during this time and I’ve met several.

Very few black men were traders back then but I’ve met a couple. They were wild.

The whole environment was just wild and everybody was on drugs and drinking heavily and just trying to make money hand over fist.

When you have Michael Milken who could pay a $1bn fine, that’s insane. It just tells you how far these guys were going in their day-to-day.

Did you get told any stories or anecdotes from that time, which you’re able to share?

I was at a concert and I met a young black woman and she was saying to me, “Where did you guys get this story idea?”

She rattled off a particular episode and she said, “That was my dad’s life; that was actually his life.”

She goes, “He used to show up sometimes in drag on the trading room floor.”

She asked him why. He dad replied, “We just did shit like that.”

It was wild. They would just do whatever they felt like doing.

She said her brother and her would always find these little straws at the house, and they would make little designs with straws like they were little Legos.

It wasn’t until many, many years later that she realised what all these little straws were.

Her parents kept going, “No, no, no, give me that!” and throwing them away. They were like, “What’s the big deal? They’re just little straws!”

Daddy, why is there so much sugar?

Yes, it’s got sugar in it! It doesn’t taste like sugar!

Where we are in this country with race relations? Where we are in this country with justice?

Do you know anyone who was affected by Black Monday or the 2008 financial crash?

The 2008 financial crash, I knew very few people and I know very few people that were involved in the stock market, who had their livelihood in that.

I didn’t really have a lot of money in the stock market at that time. Because of the volatility of it and because we weren’t familiar with it, we just kept our money in cash.

I remember our business manager at the time saying, “That’s a brilliant idea; that’s a brilliant strategy.” We were like, “Brilliant strategy? We just didn’t know what we were doing.”

We would have been wiped out, too, if we had been smart enough to put our money into stocks and bonds.

No, I didn’t really know anyone personally who was affected. I’m an actor, and most of my friends are actors, and many of them were not working.

We didn’t have dough like that to be worried about the crash. In 2008, I was still doing… What was happening in my life in 2008? That was 12 years ago, right? I think I was just putting my money in mattresses and hiding it!

In recent years, we’ve had ‘The Wolf of Wall Street’, ‘Billions’, ‘The Big Short’, ‘Black Monday’ – what is it about the real-life Wall Street that makes it such fertile ground for drama?

I think because it is relatively unknown to the population at large about how it actually works and what’s actually being done.

Once you reveal it, you realise that half of the people that are dealing in that area don’t have any idea how it’s being done either!

And how much of it is about gambling – that’s all the futures market is, right? You’re just rolling the dice and hoping this shit works out. Educated guesses but, honestly, we know about that volatility now.

We’re watching the market plunge as a result of the coronavirus. It’s just about people’s ability and how much risk they can withstand and how cautious they are and how risk averse they are.

I think it just plugs right into our deep, base, human shit. It’s just dressed up nicer in suits and fancy cars, but it really reveals who we are and how fragile that we are.

That’s the draw. And it’s happening at such a high level, and it’s so high-octane and so fuelled with ego and money and power.

A lot of times, people like to vicariously live through that without having to put themselves into that position. They’re like, “I’m going to watch you crash and burn; I don’t want to do that.”

Many of the shows I just listed are also really funny. Where do you think that comedy comes from? Are we laughing at these people or are we laughing with them?

I think yes, to answer the question. Both. I think at times it’s both. You get to see human beings stressed to the max.

It’s always a high-wire act. It’s not really mundane.

As soon as that bell hits, they’re in the pits having fist fights and threatening one another, and people are whacked out of their minds because the ability to potentially go from zero to hero is so right in front of you – and, also, to go from hero to zero. 

It’s big swings, and that volatility is dramatic and exciting and it’s going to be funny because people are going to act at their extremes trying to achieve something, and that’s what comedy is.

It’s watching people use an inordinate amount of energy toward attempting to achieve their goals, and how far they will go to achieve them, and how ridiculous people can be to achieve them – all for the almighty dollar. We’re going to see every emotion come out when that happens.

Black Monday

Donald Trump was the embodiment of Big Business, and now he’s the President. Nobody took him seriously when he started...

Yes. There are obviously a lot of factors why he’s the President, but that’s something that people were talking about when Ronald Reagan ran.

I think that was a George Carlin joke; people go in like, “I’m going to vote for the actor.” Then he wins and people were like, “Wow, shit, I was just fucking around; I didn’t think he had a shot.”

I think Donald Trump, his rise, has a lot more to do with other endemic and systemic things that are happening in this country.

Yes, he was a joke to a lot of people. There was no way it could happen for a lot of people, but it just shows you, if people don’t come out in numbers, you’re going to get what you get.

How do you think he’s done in his first term?

Horribly. People say, “Look at the African-American jobs, the unemployment rate is lower than it’s ever been.” In eight years, it was a steady decline from Obama to now. I guess he gets credit for not fucking that part up, but it’s not like it’s on him that that’s the reason.

Then you look at the negatives that far outweigh all the positives.

Where we are in this country with race relations? Where we are in this country with justice? Where we are in this country with our courts…?

I would love to be more hopeful, but I’m not right now.

That’s an alarming thought...

The trend is not our friend – I’ll just say that.

A cultural phenomenon like Black Panther hits and people go, “Oh, people want to see black stuff”

Let’s talk about you now. You were part of a collective of young actors who hung out and auditioned for the same roles, is that true?

We all went to CalArts, California Institute of the Arts, to study Acting – and when my class graduated, there were several actors, young black actors, and we were all very good friends in school.

We migrated to the same area in LA and lived within blocks of one another. We all depended on one another as well to make rent, to live, to make groceries.

We didn’t specifically pool money, but whoever had money was often in the position of helping out everybody else.

They were just my boys so, if I had an audition, I would ask the casting director after I was through, I’d say, “Hey, can you see my friend?”

We always tried to get in because one of us needed to get the job. I just always had the philosophy that they can’t get my job and I can’t get his job. It’s like we all get what we’re supposed to get.

The casting director would always say, “You know if he gets it, you’re not going to get it – there’s only one job?”

I’m like, “That’s fine, as long as that other dude out there that I don’t know doesn’t get it, because I’m going to need to borrow money from this dude so I need him or me or one of us has to get this gig.”

Is that collective ethos common in Hollywood?

No. I think it was pretty uncommon in Hollywood, based on the reaction that we would get when we would bum rush these auditions.

I think it’s set up so it’s very dog eat dog, and everybody for themselves. You are made to feel like there’s not enough work for everybody and, perhaps that’s true.

I just have my experience to go on; I never felt like there wasn’t enough.

Again, this was a different time. When I got out of school in ’86, we would be able to get these guest star spots and we would be able to get these smaller roles and supporting roles and then ten, 12, 15 years later, all of those roles were going to established actors.

Is it equitable? It’s always tricky. This business has always been tricky

People who had roles in films are doing small roles in TV and we were like, “Those used to be our parts.”

We used to be able to book these small parts and you didn’t have to have a name and you didn’t have to be somebody.

That trend started to shift. Now that there are so many places to work, there’s so much streaming and subscription and all of that, there are so many channels, there’s ability for more actors to find space but now they’re dealing with are they going to be paid fairly?

Is it equitable in that regard? It’s always tricky. This business has always been tricky.

As a young black actor, you’ve said you were always offered the same type of roles. Has that changed over the past 30 years?

I think it’s changed a lot. I think in the past few years, it’s changed pretty dramatically, in fact.

A cultural phenomenon like Black Panther hits and makes money and people go, “Oh, people want to see black stuff.” Or Us or Get Out. There was a moment when several things happened in our business, from movies to television, that the powers that be, those in positions to greenlight projects started thinking, “I can get more green if I greenlight the black projects.”

That’s always what leads it. We want to say that it’s a cultural awakening and people finally understood that these stories translate, but they understood it because it made money and they’re like, “OK, we want to do that some more.” It’s cyclical. It will go out of favour again and there’ll be another wave of trying. It’s always trying to do things in the rear-view mirror. I think we’ve rarely been forward-thinking.

Everybody wants to be the second person to have that great idea, but it’s got to work first. Everyone’s really risk averse. It has changed since when I got out of school and the roles that I was being offered were a lot of gang roles and a lot of cops. I was on one side of the gun or the other, but they weren’t very nuanced.

Several black British actors moved to America because good roles aren’t available over here...

Yes, I think that has absolutely been something that we know is the case and that we’ve seen. I don’t know a ton about what’s happening as far as TV and movies in the UK, but I know that my friends who are here from there have mentioned that it was necessary to travel to try to have more opportunities. There’s just more that’s produced here, too. There’s just more work here, period.

Don Cheadle

You were one of 19 African-Americans profiled in the book ‘In Search of Our Roots’ by Dr Skip Gates. That must have been an unbelievable voyage of discovery?

Yes – it was wild. It was amazing to see the lineage go all the way back to Cameroon for both sides of my family, from mother’s lineage and my father’s lineage, all the way back to villages that were both inside of Cameroon. The chances of that are astronomical.

I think Dr Gates told me at the time that there was only one other person that he had ever done that with who had that same experience that both families went back to one country in Africa with descendants from one country. The other one I think was Chris Rock.

Did the experience change your perspective of yourself or your sense of identity at all?

No, it was just great information to have, and it was just great to have that story generated and to be able to share it with my family. To be able to give it to my relatives and let them see, “This is our lineage and this is where you’re from.” None of them had ever done it, and definitely not to that degree: to trace our roots back and realise that our family was owned by Native Americans.

It’s such a crazy intersection of not just America’s history but also parts of America that America’s still reckoning with...

And forever will be, and in even more stark relief than we have in the last 20 years. These last four years have put it on Front Street in a way that’s undeniable, even though a lot of people still don’t want to talk about it and are like, “Why are we still talking about that?”

It’s like, “What do you mean, why are we still talking about it?” The “get over it” shit is the funniest thing in the world to me.

It’s like we’re supposed to have moved on beyond talking about the concentric circles of effect that still happen as a result of slavery and as a result of Jim Crow laws. It’s that little wrinkle of it being owned by Native Americans who, after the Emancipation Proclamation said, “We’re not recognised as Americans so we don’t have to obey the rules of your government, you don’t even recognise us as people so we’re not going to give up our slaves, we’re going to hold on to them.” The Choctaw. Thank you, Choctaw.

My great-grandmother’s mother was a slave and I knew my great-grandmother

I interviewed the actor Lakeith Stanfield a year ago. He said that to be black in America is like having your identity stolen – which echoed what you said about how many black Americans have this big hole in their history...

It’s very rare that we can trace that back, and that’s not accidental. The uprooting and disavowing of our history is the first thing that happened to us when we got here. We were separated and broken up so we couldn’t communicate and given different names, and our lineage was destroyed or hidden, and we just became chattel and that’s hard to reconcile.

I think it’s often, by people who aren’t black, overlooked as being something that should, by now, not be that significant. My great-grandmother’s mother was a slave and I knew my great-grandmother. I had a personal relationship with my great-grandmother. She lived to be 106 years old. That’s how close it is. That’s how much it still affects people who are alive today.

Of course, older people who are alive today who lived through Jim Crow and who lived through not having the right to vote, women who didn’t have the right to vote, they’re still alive. They’re alive today. So, to talk about it in terms of something that happened ‘back then’ and that we should just move on, and that it’s not a present factor in our lives, is to not recognise continuum nor give respect to history. Yes, it’s something that we continue to fight for – and is a collective trauma that we deal with.

Some people seem to have the mentality: ‘Obama got elected and that’s racism solved…’

I had a very famous director – a dude who I like and think is very smart – say to me after that election: “Well, you can’t say that America’s a racist country anymore.” I said, “What are you talking about?” He said, “We elected Obama.”

I was like, “I’m going to act like you didn’t say that, because I still have to work with you and be on this set with you, but that’s about the dumbest thing I’ve ever heard anybody say.”

Don Cheadle: Black Monday

Another film of yours, ‘Crash’, won multiple Oscars but has also been criticised for simplifying racial discourse. Is that fair?

If you’re looking to a movie to speak in a way that is all-encompassing about what that’s supposed to be… The movie was an allegory. The movie is a fable. The movie is mythological in some ways and, of course, that we would all be connected…

I don’t think the movie’s a perfect movie. I have issues with the movie, but I do think that, on balance, it was a very entertaining movie. But if it starts that conversation and gets people talking about that, even if it gets them saying, “This shit’s bullshit,” I’m like, “Cool.” It still served the function for us to really start getting into it; nothing was really talking about it at that level before. Just for its ability to be a conversation starter, even if it is polarising, is, to me, valuable.

That’s a very 2020 mentality, isn’t it? This thing isn’t perfect or I don’t like this thing, therefore it must be worthless or awful or cancelled…

It’s binary. It either has to be great or it’s fucking shit. We know that everything lives in between that. When I came on and when I read the script, I was like, “I’m in and I want to help produce it; let’s put this thing together and let’s go.”

Paul Haggis, he had a really good idea. I knew where he was coming from and I knew where his heart was and I felt the script was very ‘important’, with quotations around it, to do at that time for all of the reasons that I spoke about, not one of them being because I thought it was a perfect movie, but because it poked at something that I thought was really critical to poke at.

My mom was like, “We don’t want you to start a fight but if you’re in a fight, you better finish the fight –

As somebody whose fame precedes the social media age, have you noticed a change, an evolution? You seem to be someone who’s very comfortable in themselves.

I think I’m not. I’m as neurotic as any actor. I think it does reveal a lot and I think we get to see a lot of the id of different cultural touch points in many ways. It’s also lousy with bots and propaganda, and it is often difficult for people to filter through that, as we have seen. 

It is driving different aspects of our society. To what degree it is affecting it? We know that it has an effect on our politics. It has an effect on how we relate and the people driving it know that. Jack [Dorsey] knows that. Mark Zuckerberg knows that. They know the function of it and it’s really unfortunate that they’re not policing it better.

You’re a huge activist on climate change and Africa. Do you believe it’s important for people with a platform to fight for causes that are important for them or is that something you would do regardless?

I think I would do it regardless and I was doing it before anyone cared what the hell I had to say, and that’s attributable to my parents and that’s attributable to coming from a family where… My mom was like, “We don’t want you to start a fight but if you’re in a fight, you better finish the fight – and don’t start any illegitimate fights, but you absolutely have to fight for things that matter.”

I was raised with that for as long as I can remember, like I said, before I had any kind of a platform. I do think it’s important for those people who find themselves in a position to speak about issues that they believe are important, whatever that issue is for you.

I think that’s one of the best uses of where we are in this moment and what we have the ability to do. Definitely more important than can you cut in line and get a great seat at a restaurant or some perks in a gifting suite.

That’s all cool, but really, if you’re not taking advantage of this situation, I think you’re squandering an opportunity to do what very few people have an opportunity to do – which is take the attention and refocus it off yourself onto the people and organisations and the causes that you believe in and support, and put your money where your mouth is, and put your time and energy where your mouth is.

If I wasn’t doing that, I would feel bad about myself. I wouldn’t hang that yoke on someone else and say, “You’re a bad person if you’re not doing this.” I do wish more people would say more and, when they do, it’s very impactful.

View on Instagram

Whenever you next win an award, is there a particular subject you plan to speak on?

Who knows, A, when that will happen and, B, where we will be? It’s scary to think about where we might be in, say, four years or five years.

Even the next election cycle, what’s going to happen? Who’s going to be the President of the United States? What’s going to happen in the aftermath of Brexit? What’s going to be happening in Brazil? What’s going to be happening in Iran or Syria?

There are so many places that the tinderbox is ready to be lit, it’s pretty daunting to imagine where we could be in a few years’ time.

I think we are on the precipice of both a renaissance, an awakening and a greatness, but also a much darker time as well – and it’s going to be incumbent upon us to determine where that goes. The leadership are getting smaller and smaller, in our country especially.

Donald Trump is remaking his government in his own image, and you see with something like the coronavirus, there’s no one at the head of that organisation. He got rid of the person to take care of this shit. It’s like what the fuck is going on?

Mike Pence is now in charge of COVID…

Who gave us pray the gay away, who gave us the epidemic of HIV in Indiana that was under his auspices and under his purview. It’s crazy what’s happening right now and, if people want to talk about the progressive candidates that we have pushing things too far to be voted for, are we supposed to incrementally move towards some of these changes that we need to see happen?

How do you incrementally move toward dealing with the climate crisis? I don’t know how you don’t just foot on the gas, no pun intended, to deal with this – and think that there’s any chance that it will be dealt with. Exactly, we have somebody in charge of the thing that doesn’t really believe in science. It’s messed up.

It does feel like we’re either going to turn the corner or hit a wall...

I have kids, and our kids are looking at this generation now. I’m right on the cusp of the boomer generation, and they’re looking at us going, “What did you do? What did you leave us? What are we expected to do?” If you look at South Africa, you look at Egypt and the Arab Spring, and it’s often the young and it’s the youth and it’s the students who push the older people to do what they’re supposed to be doing.

That’s what’s happening right here on climate change. That’s what’s happening with LGBTQ rights. That’s what’s happening with diversity mandates and MeToo. All of these things are being supercharged by the youth, but the mechanisms absolutely are protecting themselves and the systems are protecting themselves and fighting back. So, yes, I think we’re on the razor’s edge where it could go either way and it’s a very daunting time.

People want to label you as a social justice warrior but what’s the alternative? To be an anti-social coward?

Have your kids “OK, boomer-ed” you yet?

“OK, boomer-ed” me?

That’s what they say, right?

Yes, that’s what they say, “OK, boomer.” Maybe they’ve “OK boomer-ed” me. I’ve been like, “The boomer may cut off the spigot.” No, I wouldn’t do that. “The boomer’s cutting the cheques right now.” I worry about them. I pray, even though I’m not religious, for them to inherit a world that’s actually for them and where they have a place.

In LA, especially with the housing crisis, homelessness here is out of control and jobs are scarce. My kids were looking with my goddaughter to try and find a place to live and they found one, finally. But trying to find apartments… there were three of them and they looked for months and couldn’t find anything.

I don’t know how it is there but here there’s an application fee, you have to spend $100 to put in an application, so a lot of these landlords really didn’t have any design on renting the place. They’re just collecting application fees.

Yes, it’s pretty similar here. Homelessness is awful in London, and it’s so widespread that we get desensitised to it…

It is human, because we are going to keep going. If you stop and come apart every time you come into contact with something that made you go there, you wouldn’t be able to move during the day. Hopefully, when you see that, you’re inspired to try to do something about it and get involved politically, get involved in the charitable aspect, and really think about how you’re living your life and try to address it.

Yes, it’s in your face all the time. In this country, a majority of the population is $400 away from a real financial tragedy. $400 away, one bad medical bill or one fall or one car accident or just one thing. They don’t have insurance and that’s their savings. People don’t have $500 in savings to deal with shit. It’s pretty bad.

Every time I go to America, I just think, “Don’t break yourself.”

It’s amazing. Again, those systems will fight back. Insurance companies will push back. We are not incentivised to be healthy. Doctors, perhaps, should be paid in the way that it used to happen where, if you were sick, that’s when you don’t pay because they’re not doing their job. Doctors should be on retainers to keep you healthy.

You don’t incentivise the illness at this point. If the money isn’t just giving you the thing to fix and not to prevent it then where’s the incentive to make patients healthy? It’s to make you healthy once you’re sick but, to keep you healthy, it’s like, “I’m not really getting dough out of that.”

It’s like what you said about the acting industry, the green being the bottom line.

That’s it. People are pretty simple in that way.

What are your personal ambitions for the next decade and beyond?

I’ve started a company, Radicle Act Productions, spelled RADICLE, which is the first part of the seed that goes into the ground and creates the thing and helps plant trees. A radical act is to get into this business in the TV, film, doc side and all of that and really try to centre voices that have not been centred traditionally, and new stories, and support new writers and new artists, and try to be an incubator – a ‘thinkubator’.

Nice wordplay. You should work for a magazine...

As long as people stick a mic in front of me and a camera in front of me, to continue to, like I said, take that attention and put it toward issues and causes and organisations and people that are really doing the hard work out there on the ground and dealing with all the things that we have to deal with.

It can be overwhelming and people want to label you as a social justice warrior but what’s the alternative? To be an anti-social coward?

I don’t know. It’s like that’s what we all need to be right now. Get in where you fit in. There are a lot of things that need to be addressed and we need to get to addressing them. 

‘Black Monday’ season 2 will resume on 28 June.