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  “We were like, ‘What is this? I never heard this word before,’ ” said Keenen. “So we asked the director. He didn’t know. We called the writer to ask what it meant. He said he just made it up. That was just the funniest thing to us: You’re making up street slang.”

  Keenen did score a slightly noteworthy role on a brand-new sitcom set in a Boston bar called Cheers, but his face was barely visible. Keenen also had the honor of getting arrested by Erik Estrada on CHiPs and booking a part opposite future Cheers star Kirstie Alley in a failed pilot called Highway Honeys.

  In 1983, Keenen’s career began to gather a little steam. He played a standup comic in the Bob Fosse–directed film Star 80 For Love and Honor, a television pilot in which Keenen played an illiterate boxer, actually got ordered to series, managing twelve episodes before petering out. Then, in October of that year, his big break: He was booked on The Tonight Show. This was still the era when The Tonight Show was pretty much the measure of any standup. Keenen had been doing standup for more than five years and had a pretty polished act, but backstage at The Tonight Show before going on, he was wracked with nerves.

  “My heart was jumping out of my chest,” he said. He’d just seen Risky Business and a line from the movie popped into his head. “They were saying my name and I said to myself, ‘Sometimes you’ve just got to say what the fuck,’ and I ran out and did my act.”

  He was equal to the moment. Taking the stage in a slick gray suit and thin striped tie, he looked energetic and at ease. His set was not only funny, it was distinctly black. After opening with a somewhat innocuous bit about the differences between California and New York, he goes into a joke about his brother Dwayne, who, he says, “finds racism in everything.” After getting fired from McDonald’s, Dwayne rails against the injustice of it all.

  “He’s like, ‘The white man don’t want to see you make it! They don’t want to see you get ahead. They got a conspiracy out there!’ Does he think there’s some secret organization sitting around going, ‘Now there are too many black people making it in this country. They’re making too much progress. Now, let’s see . . . We got Malcolm X, we got Martin Luther King . . . Dwayne! He’s up for promotion at McDonald’s! Stop him!”

  Keenen is animated, jumping between characters, trying out different voices, as he tells stories from his life. One moment he’s his dad talking to his teachers at school (“If Keenen does something wrong, you feel free to hit him.”), then he’s his mom back at school contradicting her husband (“That’s my child. I laid on my back for thirty-six hours pushing his big head out. Now, when my husband push one out, you go hit that one.”), and in the end, there’s a lesson (“Rule one in life is you don’t hit a black woman’s child.”).

  Another bit is about hitting on white women. “Every time I see a white girl that I think is really pretty and I want to talk to her, I feel like everybody in the room is watching me,” he says, before adopting the voice of a gawking white onlooker. “ ‘Look at him. He wants that white woman. That’s his slave instinct coming out.’ It’s like I’m on Wild Kingdom.”

  The crowd loved him and so did Carson, who gave him the ultimate endorsement, waving him over to sit beside him on the couch. As Keenen sits down and the show cuts to commercial, Carson can be heard saying, “That’s funny stuff.”

  “I was having an out-of-body experience,” Keenen said. “That moment was the highlight of my career.”

  When the show returns from commercial, there isn’t time for Carson to interview Keenen, but he promises, “Next time you come back we’ll have time to talk.”

  A good set on The Tonight Show and the thumbs-up from Carson could change a comic’s career back then, and Keenen noticed a few differences right away.

  “It put you in a different class of comics and made auditioning easier,” he said. More people knew who he was, and even the ones who didn’t could see on his résumé that he wasn’t a nobody anymore. The idea of a black comic on Carson was still rare enough that it didn’t go unnoticed.

  “I remember seeing Keenen on The Tonight Show,” said Chris Rock. “Just seeing a young black guy with a suit on telling jokes with Johnny Carson, I was like, ‘Wow. How’d he do that?’ ”

  But Keenen’s moment of triumph brought with it a sobering realization. Sure, more people knew who he was, and that gave him a certain cachet at the Comedy Store, but it didn’t magically change Hollywood. It didn’t suddenly greenlight a slate of black films or create substantive, three-dimensional roles for black actors.

  “It was like—you made this big impact, but now what?” said Keenen.

  7

  “I Was Young, Black, and Angry”

  February 1982. On the sidewalk in front of the Improv on Melrose Avenue in Hollywood, Keenen and Damon are huddled in deep conversation with Arsenio Hall and Eddie Murphy. It’s ten months before 48 Hrs. opens. Eddie still lives in New York, where he’s become a star on Saturday Night Live. He’s in town to tape his second Tonight Show appearance ever. His first set was funny, but relatively mild: jokes about catalogue models, kids named after breakfast cereals, and talking cars.

  This time Eddie wants to take a bigger risk. That’s the problem. His plan is to cut through the unspoken racial tension by engaging the audience in what he calls “some scream therapy.” He wants to challenge them to scream “Nigger!” at him at the top of their lungs.

  Arsenio was meeting Eddie for the first time on the sidewalk that night and recalled him telling the group that Carson’s response was unequivocal. “Johnny was like, ‘You’re not doing that,’ ” said Arsenio. It wasn’t as if Carson had a moratorium on the word or anything. The conversation on the sidewalk turned to a particular appearance Richard Pryor made on Carson back in 1976. “We were confounded,” said Arsenio, “because Johnny used the N-word with Richard.” Carson, in fact, had said to Pryor, “You use the word ‘nigger.’ Does the black community get on you for using that on a show?” As Arsenio remembered, Pryor and Carson “had a great conversation about it.”

  Maybe it was the changing times or Eddie was simply being held to a different standard, but at any rate, he’d been told no, and wasn’t happy about it. “Eddie was like, ‘I’m doing my bit,’ ” said Arsenio. “And he did his bit.”

  Watching Eddie’s routine, even now, feels like watching a masterful high-wire act performed without a net. The first clue that this isn’t going to be like his first Tonight Show appearance is his outfit: On top, he’s wearing a slim-fitting gray blazer, crisp white shirt, and thin tie, but below the waist, it’s dark, shiny leather pants. Leather, for Eddie in the eighties, is a pretty reliable measure of his confidence level. (In a Tonight Show appearance five months later, he’d be dressed in a white leather suit; in his groundbreaking HBO concert special, Delirious, the following year, he’d be head to toe in red leather.)

  Eddie swaggers onstage and announces to the audience, “We’re going to do some scream therapy, all right? When I count to three, I want the whole audience to scream at the top of their lungs, okay?” One guy in the audience screams, and Eddie ad-libs. “Wait for three!” After some laughs, Eddie re-engages. “Here we go. My count. Everybody scream. We scream”—and here he pauses almost imperceptibly—“ ‘Nigger.’ ” The laughter turns uncomfortable. Is he really asking us to scream that at him?

  “It’s all right. You’ve got permission. I ain’t gonna hurt nobody. Just wait for me to count to three, okay? Because last time I was out here they screamed it before I asked them.” Now, the laughter is harder, edgier. Eddie is essentially calling out the Tonight Show studio audience as racists. For the next minute and a half, he teases and toys with them, as he works up to his count of three. He warns against improvising. (“Just scream ‘Nigger’ . . . I don’t want nobody slipping in no ‘coons,’ no ‘Alabama porch monkeys.’ ”) He invites viewers at home to join in too. He orders a drumroll. As he starts to count off, the tension mounts. Is this roomful of mostly white people about to scream “
Nigger!” at a black man on national television? Is this really going to happen? Eddie gets to a count of two, and notes how excited the audience is—“They got their lips ready,” he says, miming someone getting ready to yell—before admonishing them, “I’m not letting y’all scream that.”

  The tension breaks. It’s not clear whether stopping short of the coup de grâce is a concession to Carson or whether it’s the entire point of the joke, but it’s as dangerous and confrontational a comedy routine as anyone will see on network television in 1982, a sharp knife in the gut delivered with a sly smile. Carson seemed to come around on it too. Once Eddie sat down with him for the interview segment after the performance, Carson commented, “Nothing like a little therapy to set the ground rules before you start work. That’s a funny opening.” But Carson also claimed to have approved it beforehand. “He asked me about it before. I said, ‘Look, go try it. Live dangerously.’ ”

  Over the next eighteen months, as Eddie’s career went stratospheric, he grew tighter with comics like Keenen and Robert Townsend, who knew him back in his Comic Strip days. He also grew close to guys like Arsenio and Paul Mooney, all of them bonded together by the cultural dislocation that came with being a black man trying to negotiate the very white world of show business. But the friendship had an unspoken hierarchy. This wasn’t a partnership of equals. By 1983, 48 Hrs. and Trading Places had hit, and Eddie was mulling whether to take one million dollars for a week’s work on a terrible Dudley Moore film called Best Defense. Meanwhile, Keenen and Townsend were praying their latest pilots might make it to air. Nonetheless, the crew would hang out together, go clubbing, and talk comedy. “When we worked together, we never worked. It was just laughing,” said Keenen. “We’d be at a club on the dance floor, music blasting, going, ‘Yo! You think this is funny?’ That’s how we’d come up with stuff.”

  Damon Wayans began visiting his big brother in California shortly after Keenen moved out there, but he still lived back in New York. He’d spent plenty of years doing not much—dropping out of school, working a series of low-wage jobs, nearly going to prison for stealing credit cards while working in the mailroom for a credit card company—but by 1982, buoyed by his brother’s success, he seemed to have found some direction in his life and was ready to try standup. For his very first gig, he wrote out his jokes on index cards and shoved them in the pocket of his leather bomber jacket before heading to the club. It was a cold night, so Damon took the stage still wearing his jacket.

  “When I got onstage I felt the heat, literally,” he said. “I guess it was nerves. I broke out in a sweat. My first joke was, ‘I come from a poor family. We were so poor my father drove a 1974 Big Wheel.’ The audience cracked up. I felt real hot, so I took my jacket off and threw it.” His jokes were still in the pocket. Too embarrassed to retrieve the cards, he stood there, blank. “I had no idea what to say.” He ad-libbed a little and ground out a few laughs. “But it was a bad experience. That was the longest five minutes of my life.”

  Not long after, during Damon’s first-ever set at the Improv, Keenen was in the audience watching. So was Angela Scott, who remembers Damon being much more subdued than during his later stage and screen appearances.

  “It takes a lot of nerve to get up there and do that, especially if your brother—who’s made a name for himself, who’s moving forward, who’s very funny—is in the audience,” she says. “Damon wasn’t an extrovert. It was more inward, head down a little bit.” But just like when they’d filmed their Kitchen Table improvs, Damon had an arsenal of characters. It wasn’t great, but “he delivered a couple of laughs,” says Scott.

  Damon improved quickly. Around this time, Melvin George was the house emcee at a spot on Union Turnpike in Queens called the Rainy Night House. “He said, ‘I’d like to come out there and try some stuff,’ ” George recalls. Damon and George drove out to Queens in George’s battered Mustang and George put Damon on last. “He just brought the house down. Even back then, he was just so sharp.”

  As Damon’s standup progressed, he followed Keenen to California, where he got a job in the Paramount Pictures mailroom and made an important fan: Eddie Murphy.

  Damon’s comedy was different from Keenen’s. Performing came more naturally to him. They both pulled material from their life growing up in poverty, but Damon’s perspective on race had a cutting edge. If Keenen seemed bemused by the stupidity of racism and prejudice, Damon seemed angry about it, particularly in his early standup. At any rate, Eddie was impressed and Damon scored a role in Beverly Hills Cop, playing an effeminate hotel employee who gives Eddie’s character, Axel Foley, some bananas.

  “Eddie gave me that role,” Damon said. “I didn’t have to audition.” Eddie’s faith was rewarded: It was Damon’s first acting job, and he was on-screen for barely twenty seconds, but he made an impact. “That [scene] got a huge laugh. I was working in the mailroom, making twelve dollars an hour, and had to quit my job because everyone wanted me to be the banana guy.”

  Eddie left SNL following the ’83–’84 season, and after one interim season with an all-white cast, Damon was hired as a featured player, presumably in hopes of recapturing that Eddie magic at SNL. It was quite a moment for Damon. His comedy life seemed charmed. “Eddie came to my celebration party when I got Saturday Night Live,” says Damon. “He said, ‘Don’t get integrated into the cast. If you want to stand out, write your own sketches. Even if you only do one sketch, make sure it’s centered around you. Otherwise, you get sucked in and become Garrett Morris.’ ”

  Damon took Eddie’s advice to heart, but it didn’t necessarily serve him well. Lorne Michaels was back helming the show after a five-year absence and hoped to bring Damon along slowly so as to avoid the Eddie comparisons. Damon didn’t have the patience for that. He was asked to play a succession of glorified extras. His ideas were routinely dismissed. He felt he was being held back, ignored, or worse, actively marginalized. Frustration set in. He took to walking around 30 Rock wearing dark sunglasses and a scowl. When someone would ask him what was wrong, he’d say, “It’s too white in here. It hurts my eyes.” He felt on the verge of a nervous breakdown.

  “They wanted me to play a slave in the sketch and hold a spear, and I didn’t have no lines,” he says. “I told Lorne, ‘My mother’s gonna watch this. I’m not standing there with no spear. Unless I could stab everybody in this scene, I’m not doing it.’ ” Michaels pleaded with him to be a team player and promised him his time would come. Damon’s manager at the time, Brad Grey, told him the same thing. Damon couldn’t see it. To him, this wasn’t about being a team player, it was about being a slave. Literally.

  It all came to a head on-air, during an exceedingly unmemorable sketch called “Mr. Monopoly.” Jon Lovitz plays the title character, a lawyer armed with “Get Out of Jail Free” cards. Damon and Randy Quaid play cops with little to do other than push the not particularly funny sketch along. When they ran through it in dress rehearsal, Quaid and Damon were dressed like Miami Vice’s Crockett and Tubbs. Damon thought the sketch stunk but at least he looked kind of cool. Michaels agreed the sketch wasn’t working, but zeroed in on the wardrobe—specifically Damon’s—as the central problem, telling him, “You look like a pimp.” He and Quaid were re-outfitted in plain white shirts, dark pants, and dark ties.

  Fuck that. Damon was angry. Angry to be in this unbelievably lame sketch, angry he was being blamed on some level for it being so lame, angry that even the faint glimmer of a silver lining he’d found had been snuffed out, but most of all, angry that this seemingly golden opportunity on SNL had curdled so quickly.

  When it came time to do the sketch live that night, he decided to give the bland, forgettable character he was being asked to play, well, something. He plays the cop with the same swishy brio he’d brought to his Beverly Hills Cop cameo, revisiting a version of the character he’d unveiled in his improvs with the Kitchen Table and, even before that, joking around as a teenager in the West Village with Keenen. Of cours
e, in the context of the “Mr. Monopoly” sketch, it made no sense whatsoever. The effect wasn’t funny or even particularly anarchic, just supremely odd. At any rate, Michaels lost his shit. He charged backstage and fired Damon on the spot.

  “I went berserk,” Michaels admitted in James Andrew Miller and Tom Shales’s oral history of the show, Live From New York. “Damon broke the big rule. The whole business of trust when you’re in an ensemble . . . We have live air, we’re not just going to go up there and say, ‘Fuck fuck fuck fuck.’ ”

  Damon had never seen Michaels lose his cool like that—Michaels hollered some version of “You’ll never work in this town again!” among a lot of cursing—but otherwise Damon wasn’t too bothered. The situation had been untenable.

  “I wanted to get fired,” he says. “I was young, black, and angry. I just knew in the moment I was unhappy and not gonna take this shit.”

  By the time Damon was unceremoniously booted from SNL, his older brother was facing his own batch of frustrations. Coming off the high of The Tonight Show, acting work had slowed, and the parade of insulting auditions grew more demoralizing by the day.

  Townsend had also reached an early career pinnacle—acting alongside an almost entirely black cast (including Denzel Washington and David Alan Grier) in 1984’s Oscar-nominated A Soldier’s Story—only to be brought down to earth afterward. The stack of scripts waiting for him after that triumph promised the usual array of roles as rapists, muggers, and drug addicts. His agent explained, “Robert, every year they do one black movie and you just did it.” Townsend was despondent: “I thought people would be so taken by A Soldier’s Story that it would be different. It wasn’t.”