Dropping out of college was the first time I felt like a real grown-up failure. I may have just broken everything. I’d graduated from one of the most exclusive and best private schools in the country. About a million years after I was there President Obama’s daughters would go there. In high school I was always the student who could have done better if he’d tried harder. My dad was always right about that. By the end of my senior year, I had a B-minus average in a school filled with kids getting so much college credit that they walked into college as associate professors. I was just looking for a college that I could get into. I wanted a big city. Midsize, not too large. And also someplace where I’d still be able to do martial arts. Back in the day, you did this by buying books so you could research colleges. When I found the University of Pennsylvania, I thought, That’s a good-sized school. It’s in a city! Only later did I realize it is an Ivy League school. Maybe I’ll be unique there. I bet they don’t have a lot of B-minus students!
I decided to apply for early decision. My college counselor said, “I don’t know about that . . . Maybe you should look at other places . . . ,” but I did it anyway. The day I got in, I brought in the letter, and she said, “I knew you could do it!” and I said, in my head, “No, you didn’t.” I realized then that people in positions of authority don’t always know everything. And sometimes they know nothing. And at seventeen, I already felt like there was a racialized component to it.
I was proud that I’d been accepted, and it took all the pressure off the rest of the year. I saw my friends feeling nervous while waiting for college acceptances in April, but the last six months of my high school experience were chill because I’d already gotten in. Jason’s last six months were chill too. He didn’t bother applying anywhere.
Once I got to school in the fall, I decided to become an East Asian studies major. Because I like Bruce Lee! And maybe I’ll be a martial arts teacher. I’ll learn Chinese, and maybe take some Chinese philosophy courses. OR MAYBE I’LL BE A SPY BECAUSE . . . I have no idea why. But then I started taking an intro to Mandarin language class where most of the other students in the class were Chinese-American kids looking for an easy A. And then I took a Japanese history class, and then I realized, I don’t care about any of this. And I also really didn’t care about my other classes. I barely got through the year. I went home, and I spent the summer dreading the return to Penn. There was nothing I enjoyed about it. I made some good friends, but the school felt wrong. It was super preprofessional. I should have gone to, say, Oberlin or Reed. I should have gone someplace where it was all, “We don’t even have grades! We just have feelings. How do you feel like you did in this class?” At Penn, if you didn’t want to be a doctor or lawyer or a nurse or in high-end finance or a guy who runs for president because he’s bored of his reality TV show (Trump, Penn ’68), then you were out of place there.
I went back for my sophomore year, looking for a community. Maybe in the arts community, but there wasn’t much there. I had come from a small private school, where I hadn’t hung out with other Black kids. I’d hung out with a Jewish Deadhead and a Jewish guitar player. Between freshman and sophomore years at Penn, I’d applied to the W. E. B. Du Bois house, where many of the Black students lived. I realized I needed to be around more Black people. I was readying The Autobiography of Malcolm X, mostly . . . no, entirely because the movie was about to come out. The book was changing my life as I turned each page. I decided I was going to make a change in my life—I was going to live with my people, in the W. E. B. Du Bois house.
I got in to the Du Bois house, but I’d also applied for, and gotten, a work-study job in the dorm that I’d lived in my freshman year. I couldn’t do both. I knew that I was at a crossroads with this decision. I can hang out with Black people, or I can take this job . . . I need this job. That meant I had to live in the dorm again. Looking back, I wonder if living in the W. E. B. Du Bois house could have created a community that would have caused me to stay at Penn. Not that I didn’t have a community, but it would have been different.
As the semester went on, I was struggling. I went home for Christmas and I told my mom I couldn’t do it. That it wasn’t working. I went back to school, and I withdrew. But I still had a couple of weeks on campus before I went home, and I found I’d strangely become the popular, funny guy. It was the first time in my life that I’d been the funny guy. I would sleep late, hang out in a friend’s room that was sort of like a lounge. He had a double room but he was living there by himself. I would just talk with him and whoever wandered through. There was no pressure to go to class, and there was nothing else to do but sit around and be funny. I think I’d been funny before, but this was the first time I had seen people regularly laugh OUT LOUD at things I said. And not just good friends of mine like Jason and Rob. A lot of these people were strangers.
Comedy was something I’d wanted to do since I was a kid, but I didn’t know how to do it. There was no Internet then. Me, Jason, and Rob talked about comedy a lot, and Jason knew I wanted to be a comedian. We’d talk about Frank Zappa a lot, because Jason wanted to talk about Frank Zappa. We’d talk about Bruce Lee, because I wanted to talk about Bruce Lee. We were best friends because we’d jump into whatever the other was interested in, from Bruce Lee to Frank Zappa to the Grateful Dead to comedy. Plus, me and Jason were funny all the time. But my sophomore year at Penn was the first time I’d really been funny around people who didn’t know me well; the first time I really actually tried to be funny; and the first time I heard people say I was funny and introduce me as, “This is Kamau; he’s hilarious!”
There was a white guy named Seth down the hall. Seth was the prototypical ’90s white guy who was really into rap music. He was the one who actually introduced me to the music of Public Enemy. I had heard of them before, but he sat me down to listen to their new CD, Apocalypse 91 . . . The Enemy Strikes Back. (The album was great, but I was of course most impressed by “Bring the Noise,” the song they did with the heavy metal band Anthrax. I basically ran to the least “Black” thing on one of the Blackest albums of all time period.) One day, Seth looked at me after I had said something that he laughed at, and he said, “Kamau, have you ever thought about being a stand-up comedian?” and I said, “Yeah, I don’t know . . . ,” but inside, I was thinking, YES, EVERY DAY! and mentally jumping up and hugging him. But I was still too cool to say it out loud.
When I dropped out it was spring of 1992. I got home and I was depressed. I don’t know if it was clinical because I never checked. But I was sleeping all day and accomplishing nothing. My mom let me have a mourning period, but my dad was super pissed. I’d been going to an Ivy League school, something he hadn’t been able to do at my age. My father wanted me to do what he couldn’t. He was in Alabama, but I could feel his presence. I didn’t have any friends at home in Chicago. Jason was—I think—in Rhode Island for some reason. Rob was in college at the Berklee College of Music in Boston. It was the lowest I’d ever been in my life up to that point. At the same time, I was burrowing deeper into bed, the LA riots happened in the wake of the cops who beat Rodney King nearly to death getting away with no major charges. MTV was covering it, and I remember Corey Glover, the singer from Living Colour, talking about the riots and racism in America. And I just thought, The world is truly an awful place, and I want no part of this. I have no idea what happens next . . . Maybe nothing happens next.
My mom told me I had to get a job, and this was in the olden days, so I looked in the classified section of the Reader, the free weekly paper in Chicago. I got a job at a place called Condoms Now, where I had to answer the phone, “Save the human race! Condoms Now.” It was on Division Street north of downtown. This is the nightclub district where people from out of town think Chicagoans party. It was surrounded by dozens of bars, and the condom store stayed open until three or four in the morning because it was trying to match the bar hours. I was nineteen, surrounded by this nightclub culture and bars I couldn’t go into. There were girls in short skirts, and beefy dudes who looked like they wanted to fight everybody, and non-beefy dudes who looked like they wanted to be beefy dudes. I was still a virgin who had never had a girlfriend. I was intrigued but still thought, This is scary. And this is not my scene.
The guy who owned the condom shop wanted it to be like a nightclub. He wanted it to be a cool spot where people came to hang out. And he was always (and regularly successfully) picking up on customers. All my life, I’d had guys around me who talked about having sex but weren’t actually having much or any sex. And all of a sudden there was this guy who owned the condom store who was actually having all the sex he could handle. I often thought he had opened this shop so he could get a discount on condoms. He became a weird sort of half-mentor to me. He’d introduce me to women and get me into the bars after hours. I was like his nineteen-year-old virginal mascot. I was having this fun, weird, but wasted life.
At the same time, my mother enrolled me in classes at Second City, which is where I slowly got the courage to start trying stand-up. When I finally did stand-up for the first time, I told my dad, and it was the biggest laugh I got out of him for yeeeeeeears. He told me later that when he told the rest of our family that I was doing stand-up, they couldn’t believe it either. I had been so quiet as a kid. But he also told my cousin Nora, who I had grown up with and who later became the award-winning writer, and she said, “Oh yeah, Kamau’s always been funny.” And he said, “Kamau’s funny?” I was funny with her because I felt comfortable with her.
—
Before I started doing stand-up, Jason had moved back to Chicago. He was in fact responsible for me starting to do stand-up comedy. He had heard of an open mic at a café near his apartment. We went and watched the open mic for about a month. The first night we went, it was awful, a truly bad night. That was perfect for me. If everyone had been great that night I would have thought, I can never do this. But because the audience was horrible (or really nonexistent) and everybody bombed, I thought to myself, I can do this as well as they can! At the end of the month of watching, I finally decided I was going to go up. The next week came . . . and I chickened out. I felt like a failure before I had even begun. Jason assured me that everything would be OK. He never judged my failures. The next week I knew I had to go up, but I needed help getting pumped up for the show. I needed some performance enhancers. About a year before, Jason had loaned me a Rollins Band CD, The End of Silence. Rollins Band was the punk rock band that singer Henry Rollins started after the end of the legendary band Black Flag. Rollins Band was much heavier than most of the music I liked at the time. But the album had a song on it called “Low Self Opinion” that I loved. In the song, Henry is screaming at someone with a low self-opinion. And the person Henry is yelling at is clearly Henry himself. I related. I did that all the time. Henry’s music also had a lot of humor in it. And because of his big personality, good looks, big muscles, and his ability to spin a quality yarn, Henry was in the process of becoming an MTV darling. He was a smart, funny, self-actualized dude. When his album Weight came out, the single “Liar” was all over alternative rock radio and the video was on MTV all the time. I was listening to that album again and again as I dove deeper into the heavier music. That was also the era of ’90s grunge, so I was getting into Soundgarden and Pearl Jam too. Never was a big fan of Nirvana. I was also still into Living Colour, and I had added some other Black rock bands to the mix: Fishbone, Urban Dance Squad, and 24-7 Spyz. When I’d go to their concerts it sometimes felt like there were more Black people onstage than in the audience.
In addition to Second City, I was also going to Columbia College in Chicago. It was a nonprofit liberal arts college with a focus on media arts. If it wasn’t a completely open-admission college, it was damn close. I used to joke that their motto was, “Are you finished with high school? . . . But not really done with high school? If so, Columbia College is for you!” I took English 101, and the teacher was seriously going over what nouns are. This was a big drop from Penn. And I was thinking, Holy shit . . . didn’t we all have Schoolhouse Rock? A noun is a person, place, or thing or . . . something else . . . Oh yeah . . . idea! I’m sorta smart. Out of sheer snobbery, I didn’t turn in the final paper for the class. The teacher told me I was going to get a D if I didn’t turn it in. Even in this easy class, I was still finding ways to not live up to my potential. But I didn’t turn it in, and when I got the report card I still got an A or a B. I don’t remember. But it was clear that the teacher just didn’t have it in her to give me a D.
So the week that I was scheduled to try stand-up for the first time . . . one more time, I was in an acting class at Columbia. We had to do monologues from the Sam Shepard play Fool for Love. I was assigned an angry, aggressive monologue about a guy who was bad to his lover, who I also think was his sister . . . It was pretty gnarly stuff, and it wasn’t really my style. We were each told to find a song that would help us prepare for the monologue, and lip-sync the song in character. The song I chose was the Rollins Band song “Liar” since it was all about a man being shitty to a woman.
In class that day when it was my turn, I put the cassette in the boom box and waited for the music to begin. When it did I was suddenly jumping all over the place and screaming (well, lip-sync screaming), “I’m a LIAR! A LIAR!” and it was fun, and people laughed. It was a good omen for my first performance later.
That night, I listened to “Liar” over and over and over and over again in Jason’s car. It gave me the courage to do stand-up that night. My performance that night was not as good as the lip synced one from earlier in the day, but it was good enough. A few of the comics said that I had good stage presence, which I later found out was code for “Your jokes sucked.” I kept going to open mics. I also started following Henry’s spoken-word career. His ability to step onstage and just talk really informed my later work. I met Henry years later when I lived in San Francisco, well before Totally Biased. I told him how “Liar” had helped me do stand-up comedy for the first time, and he said, “Oh, that’s nice.” I don’t know what I expected him to say. “WOW! Wanna go on tour with me and be best friends?” OK, that is what I wanted him to say.
But I already had a best friend, and he was kicking ass at that job. Jason came to every open mic with me for the first two years. People thought he was my manager because he was a cynical-looking Jewish dude who didn’t say much and rarely laughed. Jason had started to work at bookstores, and he had cut his hair short after years of being a long-haired hippie who sometimes didn’t wear shoes. And now he was wearing slacks and hard-bottomed shoes. Jason would only laugh at my jokes that no one else laughed at. I decided that if he was the only one laughing then I should just throw that joke away. It took me years to realize that I was doing it wrong, and I flipped it. When Jason (or my mom) was the only one laughing, that meant I should throw all the other jokes away and really work on that joke. They knew me better than everyone else. So they were laughing at the jokes that were the most me.
When you start doing the open mic scene it’s fun, no matter what city you are in. You feel like you are on a team with the other comics. You’re all living on the edge, staying up late on a Tuesday, and going to a diner later to eat pie and/or burritos and talk about your act! Everybody is hilarious, even if they are bombing onstage. And everybody is turned on. WE’RE DOING IT! We’re not living our normal lives! And we’re going to be successful in a year! Maybe two at the most!
And that’s what the first two years of open mics were like for me in Chicago. This is just so much fun! But by the beginning of the third year, some people had quit. Some people had gotten better. And some people were actually working on the road in clubs. And other people weren’t working in clubs, but they were the best on the open-mic scene. And I wasn’t in any of those groups. I was on the middle. I could go up onstage and do OK at best. But a lot of the time I bombed. I wasn’t interesting to anyone. By the third year, I’d frozen. I wasn’t really getting work, although I’d tried.
Sometimes I wondered if I’d just grown up as a comedian in the wrong time. The ’70s are my favorite era of stand-up comedy. Not even for any one individual or record in particular, but more for the totality of the era. If the ’50s were the conception of the modern era of stand-up with Mort Sahl, Phyllis Diller, and Lenny Bruce, and the ’60s were the birth of modern stand-up with Bill Cosby, Bob Newhart, and Joan Rivers, then the ’70s were like stand-up comedy’s toddler years, when it was just about having a good time, screaming to get attention, and making up its own rules. From Richard Pryor to Freddie Prinze to George Carlin to Steve Martin to Robert Klein, and many others, stand-up comedy was a real thing then. It sold millions of records. It topped the charts. It was played on radio. Comics became pop stars. They sold out arenas and still maintained an air of being slightly dangerous and outside the mainstream, where comedy belongs.
By the ’80s, comedy had been fully adopted by showbiz, and just like a six-year-old being sent off to first grade, it now had a shit ton of rules to follow and much of the bold experimentation that comedy was known for was gone. Comedy was a very solid thing to do and had a look, style, and even a uniform: sports coat (occasionally with the sleeves rolled up to say, “Look, I’m professional, but I’m also fun!”), a polo shirt or T-shirt underneath, jeans or relaxed slacks, and tennis shoes. Basically like a tennis coach at a business meeting. Or everybody’s fun uncle at a wedding. And all that bold experimentation within comedy’s mainstream that existed in the ’70s wouldn’t really return until the alternative comedy movement of the ’90s, spearheaded by Janeane Garofalo, Marc Maron, Patton Oswalt and others.
By the ’80s, stand-up was so regimented that there was a well-established career path that was almost like being enrolled in school. Start out as an opener. Get good, which many times meant going on the road. If you aren’t already in New York or LA, then move to either New York or LA. Camp out at one of the comedy clubs in whichever city you move to. Get a TV spot on The Tonight Show. Then get another one. And another one. And eventually become a star. Turn your act into a sitcom. Star on the sitcom for enough years to get syndication. At some point write a book. (If you don’t have an actual book in you, then just write down your act on paper and that will be fine.) Maybe break into movies. Maybe become a bigger star. At some point return to stand-up, even though you probably at some point said you’d never do stand-up ever again.
Of course there are things you can sub out for other things and additional things you can do as well. Like instead of getting on The Tonight Show, you could get on Saturday Night Live. And sometimes, like in the case of Roseanne Barr, it only takes one Tonight Show. Or you could do Late Night with David Letterman instead of Carson—although, despite the comedy community’s high esteem for Letterman, his show was never the path to fame and fortune that Carson’s was. Back in the early 2000s, I was MC’ing a show and was lucky enough to be working with the late and legendary stand-up comedy genius Mitch Hedberg. I intro’ed him just like he asked me to with, “You may have seen him on one of his many appearances on David Letterman.” Once he hit the stage he retorted, as he would every night we worked together that week, “I think more people have seen me at the store. Kamau should say, ‘You may have seen him at the store.’” And then Mitch would take on the character of one of the audience members: “‘Oh yeah, I have seen him at the store . . . He likes kiwi fruit.’”
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There was also the cable route. HBO and Showtime. Stand-up comedy was everywhere in the ’80s. This eventually oversaturated the market, and by the early ’90s, the boom was gone. Not just gone, but goooooooooooone. Stand-up started disappearing from TV except for big-time specials and occasional appearances on talk shows. Major cities that had multiple full-time paying comedy clubs went down to one or two. Small towns that had multiple-night runs of comedy shows went down to one-nighters. When I moved to the Bay Area in 1997, comics who had been around during the boom still regularly told the tales of the ’80s. It was usually after shows, when the club was empty of patrons and it was just the working comics who were allowed to stay after closing and the few new-ish comics who were deemed cool enough to be there too.
The bartenders would let us keep drinking (99 percent of the time for free—which led to more than one drinking problem). And the older comics would get a wistful and faraway look in their eyes and utter some version of “In the ’80s, you could work all year round, multiple shows a night, and never leave the Bay Area.” And to be clear, they were talking about getting paid to work. The putting-food-on-the-table-and-paying-rent work. And these weren’t all headliners. Many of these comics were feature acts who went on before the headliners, so they weren’t getting paid the most money. But there was enough money being made in the ’80s that feature acts could make a living, something that is impossible now unless you have some sort of mom’s basement/living-out-of-your-car situation. And forget having kids or wanting to save money. There’s a dwindling middle class in comedy just like there is a dwindling middle class in America. A comic’s best financial plan is very similar to that of a person who works at McDonald’s: lottery tickets. The only difference is that a comedian’s lottery ticket comes in the form of auditions for film and television. Auditions are like playing the lottery, except you have to explain why you picked your numbers and why you thought they were good numbers before they tell you that you didn’t win anything.
So it was in the middle of this gone, gone, goooooooone period, in 1994, that a twenty-one-year-old condom store employee named Walter Kamau Bell decided to start his career. Onstage he called himself “W. Kamau Bell” because it sounded more dramatic and he had seen A. Whitney Brown use his first initial on Saturday Night Live in the ’80s. That was a terrible year for me to start doing stand-up, but at least I had help. I had become really close friends with Dwayne Kennedy, the godfather of Chicago comedy. The second time me and Jason saw him perform, Jason approached him to meet him. Later Jason told me that he did that because he could tell Dwayne was somebody I needed to know. Dwayne was a little bit older, although I still don’t know how much older, and he was a great mentor to me for reasons I still don’t understand. Comics normally only hang out with people they think are funny. And I wasn’t funny. OK, maybe I was funny offstage, but onstage . . . Nope. And this was a bad time to not be funny. It was the total nadir of the comedy bust. The mainstream clubs were closing. There wasn’t a place to get better, and I could feel a profound lack of buzz or interest. I felt like I’d been held back a year. I was friends with another comic named Cayne Collier who had been doing stand-up since he was fifteen. We were the same age. I was jealous he had started so much earlier than me. Cayne was a natural leader, and the guy who everybody thought was going to be someone someday. That guy exists in every comedy town. The guy who people knew was going to make it . . . but didn’t. I was the guy who nobody ever thought was going to make it but keeps trying to.
Back then I had a studio apartment that cost about $370 a month, but I thought, I can’t continue to pay that much money. So I moved into Cayne’s apartment and slept in the living room for $285 a month, and I regret that decision to this day—why didn’t I just stay in my own stupid apartment and pay $370 a month? Like with the W. E. B. Du Bois house, maybe something would have happened in Chicago if I had stayed living on my own.
Onstage I was making no headway at all. I was a Black comic in the white club scene. I would talk about racism, and the audience would just pull back. A lot of Black comics would successfully do jokes about racism, but something about the way I did it wasn’t connecting. So I started not talking about racism, but then I was telling jokes that I didn’t care about at all. Student loan jokes and jokes about the year and a half of Mandarin I had taken at Penn, which was just an excuse to say “funny sounding” words. Just silliness that I wasn’t invested in, but because I could get a couple of them to work I would keep doing them. My big closing joke at the time—which is hard to even talk about now—was about how guys’ sexual fantasy is for a beautiful woman to say, “I want you to take me home and make love to me ALL NIGHT LONG.” But how my sexual fantasy was for a woman to say, “I want you to take me home and . . . JUST DO YOUR BEST! JUST TRY REAL HARD.” That was the first joke I wrote that ever got a real hard laugh, and it became my closer. So one thing, at least, was going well onstage. Two things, once I wrote the joke about the blow-up doll. So in other words nothing was going well onstage.
—
More and more through my time in comedy, I was realizing the difference between Black and white comedy circles, and that I didn’t really fit into either one. It was the same problem I was having with “Black music” and “white music.” I was again not fitting in. Which sucked because Chicago definitely has a history of Black comedy, and it would have been great if I had felt that I could fit into it. There was a club at the time called All Jokes Aside, which was the first full-time Black comedy club in Chicago. I would watch Black comics on TV and I would go see Black comics playing the white rooms, and I was very aware that they were speaking a language that I wasn’t speaking. This was around the same time that hip-hop was really grabbing the nation by the throat. There was a nightclub called the Cue Club, and one day a week was called Heckler’s Heaven, which ended up being a very Black night. It was a night when the audience was encouraged to heckle performers. It was run by a Black comic, and the whole idea was that if the performers were heckled by the audience, they had to get off the stage, and the audience would throw rubber chickens at them to get them off the stage. I would go there and think, This is awful. I don’t want any part of this. I don’t want to perform here. It made my stomach hurt just to watch the show.
Around the same time, a new club opened up in Chicago. It was on the North Side of Chicago, which means it was not a Black comedy club. Dwayne got me a guest set one night. I was going to do seven minutes in a real show at a comedy club to try to impress the owners and get work. I was excited. I also wasn’t really ready, and I knew it, but I thought I might be able to pull it off if I hit it hard and was confident. (I didn’t realize that I was confusing “confidence” with “bravado.” A mistake all men make more than once in our lives.) I went with Dwayne to the club. It was packed, and all the comics were hanging out in the back watching the show. I was super nervous. This was around the time when Rodney King was back in the news. It was a couple years after the LA riots, and he had been pulled over by cops again. These cops didn’t beat him, though, so things were looking up for Rodney. I decided that I wanted to open my set with it, but there was a small problem . . . I didn’t have a joke about it. These days I do this regularly: if something’s happening in the news, I’ll open with a joke about it. But these days I actually take the time to make sure I have a joke.
But I should have known that the stakes were too high to be fooling around on this show. There’s a pretty hard and fast rule in comedy: Don’t do new material when you are trying to get a job or impress someone. Before I went on, I was going back and forth between doing something about Rodney King and just sticking to my old jokes. But I think I also knew my “old jokes” weren’t that great either. Meanwhile the comedy club was feral. The MC was onstage giving out prizes and tickets to get people excited about the new club opening. Classic mainstream comedy club stuff. Some clubs never seemed to think that stand-up comedy is enough to please an audience, so there were raffles, a ticket giveaway, and trivia contests. “And let’s sing ‘Happy Birthday’ in case anyone in here has ever had a birthday ever in life!” And even though this club was on the North Side, there were a lot of Black people there that night. The room had way more energy than I was used to dealing with in empty coffee shops. Next thing I heard was the MC asking a trivia question: “What’s the name of the pink Power Ranger?” A Black woman excitedly exclaimed that she knew the answer. She won the tickets. I thought that was funny: Black people—we don’t know our history, but we know who the Pink Power Ranger is! I decided it would be funny to say that when I got up onstage.
They introduced me and I went up. I had that “new comic” smell. I began with, “Black people, we don’t know our history, but we know who the pink Power Ranger is!” and the crowd turned on me immediately. They booed. And they were right to boo. It wasn’t a joke. It was just a snarky statement for no reason. An attack on someone for no reason at all. This woman was probably a mom. That’s probably why she knew who the Pink Power Ranger was; she was a good mom. I understand that now. I can name all of the animals on the Disney Junior show Octonauts, because I’m a good dad. Here we go! Kwazii, Captain Barnacles, Tweak, Tunip, Dashi, Shellington, Peso, and Professor Inkling. Just because I know that doesn’t mean that I don’t know that Madam C. J. Walker is America’s first female self-made millionaire of any race. That night at the club when I made fun of that woman, I was an asshole . . . a young, insensitive idiot.
While I was getting booed, I decided to downshift into some classic WKB material to dig myself out of that hole. Maybe a good time to talk about blow-up dolls? Nope. I went with my new half-baked topical joke. “Rodney King was in the news . . .” Ten seconds later I had been booed off the stage, in front of all the biggest comics on the scene who were all there to check out the new club.
One comic said to me, “Well, sometimes you eat the bear, sometimes the bear eats you.” It was a terrible feeling, and if it happened today, I would have just left. But I was there with Dwayne, and he was still hanging out. The comics who didn’t know me did the only thing they could do. They avoided me like I was radioactive. And I stood there, trying to figure out where to go and what to do . . . and how to stand so I didn’t look like I just bombed my face off. I was hoping that maybe it wasn’t as bad as I thought. But it was. If you’re friends with comics, they’ll joke around with you when you bomb. But my only friend there was Dwayne. And Dwayne was talking to other comics. I was just standing in the back of the club, steeping in failure juice, feeling like I had made a bad choice with this comedy thing.
And while we are talking about getting booed off the stage, as much as people think that happens a lot, it doesn’t happen that often. Most comics can survive bombing for a whole set. Knowing how to bomb successfully is part of the gig. You can’t always just run away. At the very least the club needs you to fill your time. There aren’t comics in cages backstage waiting to go on in case of emergency. Sure, there are comics hanging out. And many a comic has been thrown up onstage when the club has had a need for another comic for various reasons. But the type of bombing that I did that night is pretty rare. The feeling of that bombing is rushing back to me right now as I type this. That had been my shot! There was no other club in town where I had anything close to a shot at getting up. For all intents and purposes, I was retired.
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Being in my twenties was not helpful for my comedy development because I had nothing going on to talk about. It wasn’t until I got to my thirties that I had real material. It was only when I got older that I found the right things to talk about and the right way to talk about those things. But one of the best things about being a young comic is going out to watch as many stand-up shows as you can. You are hungry for knowledge. It doesn’t matter if you like the comics on the show or have even heard of them. If you aren’t onstage then you should be in a club watching other professionals onstage. One night me and Cayne went to All Jokes Aside to see one of Cayne’s favorite comedians, a young Black dude named Dave Chappelle. At the time I was twenty-one and I later found out that he was twenty.
Me and Cayne arrived and were seated in the center of the room. We wondered why they put us there. The show started, and one by one, comics (all of them Black) came onstage. And they were all killing. And it was hilarious. But it wasn’t a style of comedy that I felt I could pull off. It was raw, dirty, filled with references to rap songs I didn’t know and talk of a Black experience that I didn’t have growing up. At this point I was watching Janeane Garofalo and Marc Maron, and I was starting to really get into Bill Hicks. All three of them do black comedy but not Black comedy.
This was the Def Comedy Jam era on television. HBO’s Def Comedy Jam became famous when Bernie Mac, on an early episode, had to follow a comic who had just bombed. Bernie stepped onstage, surveyed the crowd, and proclaimed, “I’m not scared of you motherfuckers,” and it killed. The audience was fully on board with Bernie that night . . . and for the rest of his career until he died. But there was a problem. I was scared of those motherfuckers. That’s the energy of Def Jam—you need to be combative. There’s nothing about comedy that made me want to be in a combative state. It was the same energy that resulted in throwing rubber chickens. And I think it comes from Black people’s experience in this country, having to defend ourselves at all times. Having to be loud in situations where other people might not be loud, because if we aren’t loud there’s no chance of getting our share. If you’re loud you still might not get your share, but you might get more than they’d give you otherwise. And when you’re told to be quiet all the time, or to obey, or to shut up, when you’re finally in a place that’s yours, you can let it all out.
America’s favorite pastime isn’t baseball. It’s telling Black people to behave . . . even when we aren’t doing anything wrong. So I get it, when we’re in a room with a lot of other Black people . . . and that room is run by Black people . . . and no one’s telling us to “behave”—then we make sure that we have a good time. And ain’t nobody got time for an unfunny comedian. But back then at All Jokes Aside, I saw Black comedians up there with this aggressive style. I thought, That’s not how I want to do it. I don’t want to go onstage and feel like I have to tame you or beat you back. I’ve been doing comedy long enough now that I can handle those situations . . . mostly, but I still don’t go to those venues that often. I don’t seek them out. I got into comedy to share my weird thoughts and seek connection. I can handle hard crowds of all races, but I don’t want to deal with it. Some comics get excited dealing with it. But it’s still not my thing.
So me and Cayne are at All Jokes Aside, and Dave Chappelle comes onstage. He’s skinny. He looks sixteen. And his energy seems way too relaxed for the room. I’d seen him on HBO’s Comic Relief. This was the first time I’d seen him in real life. And while nearly every other comic onstage that night had made jokes about me and Cayne that were all some approximation of “What’s this Black guy doing here with this white guy?” (We finally figured out that was why they had seated us in the center of the club. We were target practice for the comics), Chappelle didn’t do that. He came up in Black clubs and white clubs and clubs where everybody hung out in Washington, DC. So it was not a big deal to him that a Black guy and white guy were together. He was just onstage to do his jokes. And me and Cayne are loving him. He’s killing us, but in the room he’s doing just all right. So much so that people are getting up and going to the bathroom while he’s talking. He commented on it: “So many people are going to the bathroom, I must be the bran muffin of comedy.” We thought that was hilarious. We were two of the few in the audience who did. After the show we talked to him. It was easy. He was standing by himself, like I had been on the night of the Pink Power Ranger. He clearly realized that he hadn’t succeeded with the crowd, even though we thought he’d been awesome. He asked if there was a nightclub he could go to in town, and I wasn’t the nightclub type, but I mentioned a place that constantly had ads on the radio. He asked if they let people in who aren’t twenty-one yet, and that’s when I realized he was only twenty. I thought, I couldn’t have done as well as he did here, and he’s younger than me. And then he disappeared into the night.
Years later in San Francisco, I would spend a lot of time with Chappelle . . . OK, it was really only near Chappelle. The Punch Line was one of his favorite clubs in the country. And I tried to be there whenever he performed. It had only been a few years since All Jokes Aside, but by the late ’90s, even though he wasn’t famous, he was packing the clubs. People knew he was a future legend. I was in the room when he told people he had just finished making a movie about weed (Half Baked). And I was there one night when a KKK member went onstage and hurled insults at the audience. It was hilarious, because we could see his Black hands under his white sheets. Later we all realized that we were there during an early tryout of Clayton Bigsby, the blind Black KKK member that Dave played on the debut episode of his behemoth of a sketch show, Chappelle’s Show.
Once he returned from South Africa after he left the show and Comedy Central, me and Kevin were very established comics in town so we got to open for him a bunch of times. But I wouldn’t say that we were friends with him. There was a lot of competition for that by then. And me and Kevin didn’t want to try to push our way into the greenroom to see if we could buddy up. Dave would show up in San Francisco unannounced, and the Punch Line would basically book as many shows as he wanted to do. Sometimes they would bump other headliners for Dave. Sometimes they would just book ten p.m. and midnight shows for Dave. Because he always went long onstage, sometimes the midnight shows wouldn’t start until two a.m. I saw Dave do two- and three-hour shows regularly. Once I saw him do four hours and fifty-nine minutes. (He didn’t want to do five hours because he heard that was the record, and he didn’t want to break it.) At one point I got to go on the road with him and do a few cities in the Midwest. Dave always made sure I got paid more than it said in my contract. And he told me that I was funny. That period when he came back from South Africa was the best comedy I have ever seen in my life. And it’s all in the ether. Oh, it was recorded. Dave recorded all of it, but who knows if any of it ever sees the light of day. And take it from me, even if you do hear any of it or see any of it, it won’t be the same as being in the room. Like the difference between watching someone cook on TV and actually eating the food. The former is fun, but so not the point.
But at All Jokes Aside in 1994, I was just a customer who had paid to see Dave Chapelle. Because I didn’t work that club they didn’t know me (or Cayne), so we couldn’t get in for free since we were comics. And I certainly didn’t tell them that I was a comic. Which was weird, because wasn’t I supposed to want to be in that room? Shouldn’t I have wanted to be a part of that scene? I didn’t. And that sucked because the “white” spaces weren’t that accepting of me either.
And that’s how it continued until I moved to San Francisco. I needed a place with opportunity where I could grow, and I had heard that San Francisco was known for encouraging difference. I was realizing that I might just actually be different. I realized, I’ve got to make my own space.