Business Manager: You’ll get more work, I’m sure. We’ve seen people go through this before. You’ll be—
Me: Hell no, I won’t. I can’t pay that right now. I’m gonna keep that thirty grand I got left and just owe it all. Whatever happens happens.
Nobody ever told me how taxes worked. I figured that when I made the money, they removed taxes and the rest was mine to keep.
When I was younger, my mom did my taxes. In Hollywood, my business manager took care of them, along with the rest of my bills. But no one ever called and told me about these installment plans.
That’s when the enemy of success started looking for me, trying to see if there were any weaknesses in my armor. His name was bitterness.
Suddenly I knew the TV lineup for every day of the week. I could recite the Monday morning shows, the Tuesday afternoon shows, the Wednesday evening shows. Every halfway-decent and hardworking comedian’s name seemed to be on that goddamn schedule but mine. Not only was my name now a liability, but so was my attitude. I’d lost my confidence.
Struggling when you’re going somewhere is exciting. Struggling when you’re not getting anywhere is challenging. But struggling when you’re going backward is hell.
Pilot season came and went, and I didn’t book anything. My only opportunity came from Judd Apatow. He was working on a new film, The 40-Year-Old Virgin, and asked me to audition for one of the leading roles. I loved the character and felt Judd had written it for me.
I killed the audition, then found out two weeks later that another comedian, Romany Malco, had gotten the part. As what felt like a consolation prize, I was given a small, two-minute role in the film.
I thought my career was over after that. This was my last chance. How could I not get that part? If the director who’s been my biggest supporter isn’t giving me a starring role, then I’m definitely not getting a part from someone I don’t know.
One of the most stressful things in the world is to live outside your means. As my savings dwindled to nothing and I went into debt, I started getting stomachaches that were so intense, I’d double over in pain. I worried that I was developing ulcers or irritable bowel syndrome or worse.
Occasionally, I’d get a college or out-of-town club gig that would help me pay the bills, but half the time I only made enough money to cover the expense of traveling there.
Outside of Na’im, who I brought as an opener for my out-of-town shows, I didn’t tell anyone how much I was struggling. Even if I was failing, I could at least look successful. I still had my car, watches, and jerseys—at least for now. I didn’t even let my mom know how broke I was. Lord knows the level of worry she would have had if she’d found out her son was going through hard times twenty-seven hundred miles away on the West Coast. I knew she would have sent me a check, but I didn’t want to be in debt to her again. I was determined to figure a way out of this by myself.
Then one night, my Z71 was stolen.
This was my bottom. It felt like God had parted the clouds, sat down, taken a giant yearlong shit on me, and then used my car for toilet paper.
I was talented. I was funny. I was likeable. I was experienced. Yet none of those things was doing me any good. I was wasting my life away in clubs where I couldn’t afford the drinks anymore. I was, I had to admit—for perhaps the first time in my life—doing everything wrong.
That’s when I learned the biggest lesson of all: humility. In the depths of my disappointment and failure, I understood that nothing in this life is guaranteed. One day you’re hot, the next you’re not. One day you’re rich, the next you’re poor. One day you’re free, the next you’re in jail. One day you’re alive, the next you’re dead.
You can work hard. You can be talented. You can know all the right people. You can follow all the right lessons. You can be smart, rich, beautiful, everything—and still, life can deal you a bad hand.
So what are you to do in the face of a reality that can be indifferent, cold, even cruel? All you can do is play the odds. If you choose to give up, you can be fairly certain that life will pass you by. But if you choose to try your best, you can at least tip the balance significantly in your favor.
Life is not about the result—we all have the same outcome in the end. Life is about the effort you put into it. And I wasn’t putting effort into my craft anymore. After months of spiraling debt, domestic disputes, and career rejection, it was time to take a hard right turn and start doing the work myself.
Fuck being someone else’s plus-one at the same clubs every night. Fuck calling Dave Becky every day, hoping that some executive saw something special in me. Fuck paying sixty-five dollars an hour that I can’t afford for an acting teacher when I’m not getting booked for anything. Fuck living a lie with Torrei and having the same argument over and over. Fuck all this idle time. It was time to get out of this city, take my career back into my own hands, and get on my grind again.
If I was going to call myself a comedian, I needed to actually be doing comedy. I called Dave. “Dude, I just wanna do stand-up for a while. I need to get out of L.A. and work the road for as many nights as I can. I wanna go everywhere.”
After asking five times if I was sure that this was what I wanted to do, Dave finally said, “I can find a booking agent to help you, but the shows aren’t gonna be glamorous.”
“Just book me anywhere. I don’t give a shit where it is. I’d rather be performing for five dollars again than sitting around waiting for the phone to ring.”
Within a month, I was on the road—and that’s when the quiet storm of Kevin Hart began.
Life Lessons
FROM LOSS
* * *
If you experience loss, it doesn’t mean you lost. It means you’ve been blessed with an opportunity to take a moment, realize how special someone or something has been to you, and go through new doors that were closed to you before. No jokes here. Just wisdom.
Me and Kenneth with Mom
65
* * *
THERE ARE TWO KINDS OF HUSTLERS, AND BOTH ARE WORKING FOR ME
Thus began the Road Warrior era: seven straight years of touring, practically nonstop.
While I booked myself into clubs, Dave found me a personal appearance agent named Glenn Ruskow, who put me on comedy package shows at small theaters. On paper, these looked like a great opportunity. I was performing with comedians like Bill Bellamy and Katt Williams, and each show paid around five thousand dollars.