Author, inspirational speaker and extraordinary businessman. Back when you were just trying to put food on the table, were your dreams this big?

My dreams were this big but some parts of it I could have never even imagined. No one ever lives their life thinking, “This will make a great movie.” You don’t. But did I have the dreams? Yeah, and the dream was that I always knew I wanted to become world class at whatever I did with my life. I don’t want to be good at it, I don’t want to be pretty good at it, I want to be world class at it. I had a mom who told me from the very beginning that you can do or be anything you dream to and I believed it.

Can you even imagine how different your life would have been if your mother didn’t tell you that?

My mom was telling me everyday you can do or be anything so that was it. But there is a window and once that window closes it’s hard to open it back up with possibilities and dreams and plans. I remember hearing Dr. Martin Luther King Jr. say that whatever you’re going to do with your life, you should seek to become the best at it. I believe the exact words were, “If you’re going to be a garbage man, you should seek to become the best garbage man.” I heard those words as a young guy and that became part of what I call my spiritual genetics. I’m working on my new book right now, “Spiritual Genetics and the American Dream”, that I’m tremendously excited about. It’s about this whole idea of how we become who we are.

You even have Oprah Winfrey intrigued about your theory of spiritual genetics. 

I mentioned it to her once in a conversation and she called me the next day and asked, “Spiritual genetics? I’ve never heard of that, what have you been reading?” I said, “I haven’t been reading, I’ve been writing.”

How does it feel knowing the clip of Will Smith portraying you making cold calls in “The Pursuit of Happyness” is still played today to inspire sales teams around the world?

That is so cool. So many parts of the film became iconic. For instance, there is the scene that takes place on a basketball court. Our screenwriter Steve Conrad is from Chicago and he has a very dark view of the world. When that little boy throws up the ball and says, “I’m going pro,” the father in the original script says, “Forget it, you could never do that. I was no good at it so that means you can’t do it.” I waited until we were going to film that scene that day and I went up to Will Smith and said, “You can’t tell that to that little boy,” because that’s not what my mother told me. Will Smith, our director Gabriele Muccino, one of the producers and I had a very intense discussion about it. The producer’s position was that the father has to keep it real with the kid. My position was, “Man, you live in Hollywood. What do you know about keeping it real?” After 30 minutes it was Will Smith that said, “You know what? Chris is right because my mom told me the same thing,” and we tore up the script and what we wrote was, “Don’t ever let somebody tell you you can’t do something. You got a dream, you got to protect it. You want something, go get it. Period.”

Is it still surreal to watch a movie that’s based on your life?

The movie is so different for me. As a viewer you’re watching it and you’re seeing that one moment the director is capturing of that day but anytime I see any piece of it I can see the whole day. Does that make sense? I can see the whole day and everything you didn’t see on the film so for me it’s a totally different movie. Will and I were talking about this not too long ago and we both agree that if the film came out today maybe it wouldn’t have been as well received.

Why do you say that?

Because so many people right now for the last five years of this global financial crisis are finding themselves in positions that they never thought they would be in. There are people now in the position I was in then who never thought, “This could happen to me.” They went to school, worked hard, played by the rules, colored within the lines and then [snaps fingers] the world changed.

Are you and Will Smith still close?

We’re getting ready to do something here that I wish I could show you but I can’t yet. Let me just say this, it looks like Mr. Smith and I are going to do something on television. The last time we worked together it turned out pretty good.

You’ve said that at first you were hesitant about him portraying you.

I will never forget the first time I met him and we had dinner at his home. I made the decision I was going to trust this guy. I was going to be open and let him do what artists do, to slice and dice and cut and paste and tell stories. Two hours into our dinner and about halfway through he starts looking at me, he had begun to study me. I had never been studied, I didn’t like that sh-t! [Laughs] He said to me, “Playing you is going to be harder than playing Muhammad Ali because everybody knows Ali. They know the stories, they know what happened, they know how they reacted. Nobody knows you.” And right there on the spot he asked me, “I want you to be on the set every day of filming,” and what I figured out was when everybody else was watching him for 17 weeks he was watching me. He watches how you move, how you express yourself, how you show tension. It was to the point where in the last scene of the film where he got the job he clapped his hands in a certain way, he squeezes his head like it’s a melon where you can just feel the energy through the screen. That was all because he was watching me. There was as scene in the film where he had to sign a copy of my name on a contract and he signed an exact replica of my signature. This boy is good, man!

Were there other actors gunning to play your character?

Denzel Washington wanted to star and direct but he was too old. The truth of the matter is you can make a young actor look older but you can not make an older guy look younger. Spielberg also wanted to direct but it was Gabriele Muccino who said one thing to Will Smith that made Will say, “That’s the guy I’ll take direction from.” Gabriele at this point in his career had never directed a Hollywood film and could not speak English. He had to take crash courses in speaking English just for the interview with Will and what he said was, “Whatever you do, do not let an American direct this film, because Americans don’t appreciate the American dream.” That was the thing that made Will go, “Wow,” and that is why the film has done incredibly well all over the world. Come here, let me show you something. See all of those [movie] posters [from all over the world]? Isn’t that cool? We have about 30 more but we don’t have any more walls to put them on! This place is all glass.

Are Will and Jada as cool and down-to-earth as they seem to be?

Job one for Will and Jada is mom and dad, they’re really clear on that. This other stuff over here, that’s just what they do and how they pay the rent. I ask Will the same question all of the time, “How does this happen, how do you do this? Number one box office movie star in the world, two-time Academy Award nominee and third best actor in your own house. What’s up with that?” [Laughs] They are sincere, real, genuine, warm, loving people. And Will has this sick, twisted, perverted sense of humor.

How has your idea of “happyness” changed over the years?

I’m healthy, I get to do what I want to do with my life, I work for myself, I’m one of the best and I have a 5-year-old granddaughter. I went on a run that lasted 25 years and got out on my own terms at the absolute top. There was a point in time where there were 35 people out there working in this office but my life changed dramatically. One year, 5 months and 13 days ago I lost the love of my life to brain cancer. Some of the last conversations that she and I were having was her asking me, “Now that we can see how truly short life can be, what are you going to do with the rest of your life?” That changed my world. I started saying to myself, “What am I going to do? Just because you’ve done this for the last 30 years doesn’t mean you have to keep doing it. Are you happy doing it?” I’ve written books about it, I’ve talked about it and it was time to start taking some of my own advice. Holly passed on July 1^st, on July 2^nd I walked away.

What gets you through painful times?

For me pain is knowing that when I go home she isn’t going to be there, everything else pales in comparison. I don’t know if anything else has hurt that bad. When my mom passed a good friend of mine asked me, “The most important things in life, were they things you saw or things you felt?” My response was they were things that I felt. He came back with, “Well if the most important things in your life are things that you felt then the relationship with your mom is not over, it has just changed.” and I’ve had to think of it that way. I can’t see her physically but I feel her. I still talk to my mom everyday, we have the same conversation everyday and I have to do that with Holly. I know this for a fact, I will never be loved like that again. It isn’t going to happen.

What kind of love was it that made it different than anything you had ever experienced?

Unconditional. Absolute unconditional love. That means somebody that knows you, knows all of your sh-t and loves you anyway. That isn’t going to happen again. I don’t even need a woman to love me now, if she just likes me that’s fine. [Laughs] I already know what that means, I know what that felt like and the greatest honor that I’ve ever had in my life was the honor to be her primary caregiver for the last three years of her life when we fought brain cancer. She knows I was there and that gives me a sense of peace. To tell you the truth I was in denial, I was the guy that kept saying, “We’re going to be okay.” When you go through something like that with somebody that you love they can’t know that you’re scared too. When you look in their eyes and say, “No, baby we got this,” they gotta know you mean it.

How was it that you met Holly, the love of your life?

Right over there. There’s a health club at the gym and I saw this woman. I’m on the treadmill, doing my thing and this woman came out. She was 5-foot-11 and doing a post-workout stretch. While standing, she takes her left leg and put it behind her ear.

She knew what she was doing.

It worked! And for 20 years, man, it worked.

Would you say the best years of your life were here in Chicago?

Oh, absolutely. I came to Chicago from New York with $100 and a dream. The truth of the matter is historically if you look at African Americans who have created real wealth in this country, a significant number of them did it here in Chicago at that period of time. If you can not do it in Chicago you aren’t gonna do it anywhere. This is Timbuctoo and does that mean it’s perfect? No. I’ve often described Chicago as a great big lovable puppy who once and awhile takes a dump in the living room. You know, what you gonna do? [Laughs]  I mean, we’ve got millions of problems. One of my greatest disappointments with every leader in this country is that Chicago has become America’s killing field. You’re the president of the United States and you say you care about Chicago but Chicago has become America’s killing field on your watch. That’s a major disappointment.

Being on the road so often, are you looking forward to being home for the holidays?

I’m not a Christmas guy, I’m not! I did that with my kids, I had to. I was a single parent for 27 years so you have to be mom, dad and Santa Claus. That’s a lot right? Now I’m just papa and Santa Claus. To have my 5-year-old granddaughter come and ask, “Do reindeer really fly, papa?” Come on, what do you say? I’m not gonna be the one to ruin that.

That’s a great picture of you and Nelson Mandela.

That’s in his office in Johannesburg. That’s my other son, a boxer. I want to be him when I grow up! I believe dogs just know stuff. I keep lookin’ at him thinking, “Talk! I know you can say somethin’!”

If you could have a drink with anyone, who would it be?

I’d have some wine with Jesus. And I’d want to watch him make it! 

KIRSTEN MICCOLI PHOTOGRAPHY