Girl Meets Boy

In an industry where female executives too often feel they must imitate the brash, low cunning of the worst of their male counterparts, Monica Lynch was (and remains) a breath of fresh air. Unfailingly kind, intuitive, and innovative in her role as president of Tommy Boy Records, Lynch deployed soft power to attract new talent and new sounds to her label during the volatile hip-hop decades of the 1980s and ’90s. “We always did best with material that was different from whatever the rest of the market was doing at the time,” Lynch recalls about the string of breakthrough 12-inch singles that began with Bambaataa’s Soulsonic Force, then grew to include landmark recordings by Planet Patrol, G.L.O.B.E. & Whiz Kid (which begat the Double Dee & Steinski “Lessons” tracks), the Jonzun Crew, Stetsasonic, De La Soul, Queen Latifah, RuPaul, Digital Underground, Information Society, TKA, Club Nouveau, Naughty by Nature, Coolio, and various soundtracks and compilations.

But how did a white, female high-school dropout from Chicago become a top executive at one of the handful of DIY indie labels helping to establish crossover markets for New York’s hip-hop production boom? In retrospect, it seems a minor miracle; but at the time, Lynch saw it as the same odd combination of fate and luck that steered her away from the fast money in topless dancing and created more wholesome employment options for fun-loving young adults, like herself, who’d migrated to recession-era New York to make a living from music, art, or performance. 

Lynch was barely twenty-one when she abandoned the experimental nightlife of her native Chicago to enter New York’s rapidly changing cultural scene. While I spent 1978 in New York doing temp work and writing my first concert and record reviews for various downtown publications, Lynch flew in one day for a temporary stint as a model in a friend’s fashion show, then cashed in her return ticket and never looked back. Seven years later, we were both executives in the record biz.

By 1985, I was hired by A&M Records to be their East Coast director of Black music A&R, and Lynch saw herself deservingly elevated from vice president to president of one of the most distinctive hip-hop labels of the 1980s in Tommy Boy. Despite the popular—yet somewhat disingenuous—narrative currently circulating that the 1980s and ’90s were particularly sexist and repressive decades for women in the music business, it was still possible—then as now—for women to rise to dizzying heights on personal merit and integrity alone. Monica Lynch is one of many female shot-callers of that era (ranging from legends like the late Sylvia Robinson of Sugar Hill Records to Brenda Andrews of Almo-Irving Music Publishing) whose mere existence proves that the recording industry offered tremendous opportunities for women with sufficient imagination and intelligence. 

New York near the end of the twentieth century was a wild and woolly environment to be sure, but Lynch argues that women benefited as much as anyone else did from the era’s lack of rules and restraint: “I would say that there are lots of important women who helped build and run indie labels during the early 1980s that should get name-checked for their contributions. Ann Carli of Jive Records would be one person whom I would certainly consider a peer. Others that come quickly to mind are Cathy Jacobson Monaco at Streetwise; Jenniene Leclercq, who worked closely with Eddie O’Loughlin at Next Plateau; Dee Joseph at Prism/Cold Chillin’; Ann Goodman at Pop Art; Lynda West, who shaped the Fat Boys career with her husband Charlie Stettler; Lisa Lipkin at Profile; and of course Heidi Smith, who didn’t necessarily have a big title but was Russell Simmons’s right-hand person, and kept the trains running on time at Def Jam.”

Of course, Lynch’s perspective on this is not framed by wealthy major labels like MCA or Warner Brothers, where VP titles were occasionally granted to female publicists or the rare woman in retail or promotion who proved herself as tough and ruthless as the boys. Her frame of reference was informal start-ups whose visionary label heads were lucky to have a single employee of any sex, and executive titles were less important than how hard and economically you worked. As the first full-time employee Tom Silverman hired at Tommy Boy, Lynch had to participate in every aspect of running an indie label while officially only being the owner’s “office manager.” With instincts honed by a DIY punk aesthetic she’d embraced first in her native Chicago, then re-embraced (with feeling) after she’d relocated to downtown New York, Lynch’s vision of herself as a woman in the record biz was that of a streetwise optimist, just as capable as anyone else of successfully making things up as she went along. 

“It was a very small world at first, and there weren’t a lot of labels,” Lynch admits. “It was still a cottage industry, and it was New York based for the most part. So we pretty much all knew each other. But I think that hip-hop opened doors not only for a lot of women, but also for different kinds of indie and Black entrepreneurship that grew to function in a whole new way. It really started as a dollar-and-a-dream environment. Things didn’t cost a lot of money, so it didn’t cost you a lot of money to give somebody a shot. I hired a lot of people over the years, and it was typical that someone might start out working in the mail room, then become senior vice president of sales.”

The entrepreneurial nimbleness of most indie labels during the final decades of the twentieth century pivoted around their ability to anticipate and service the dance-club market. Relying upon the 12-inch single as a primary marketing tool, Tommy Boy consistently broke new artists at the retail and radio level by getting irresistibly catchy street anthems into the hands of DJs around the world. College radio, mobile jocks, and underage urban “juice bars” like T-Connection in the Bronx, or the Funhouse (later called Heartthrobs) in Manhattan, became equally influential in establishing hits for Tommy Boy. Like many indie labels, Tommy Boy had eclectic taste. They threw in with emerging trends as experimentally distinct as electro, dance-oriented rock, hip-hop, Latin freestyle, and alt-R&B—all of which then fell into the catchall category of “underground dance music.” Indeed, the subversive collision of high and low culture, facilitated by a wide range of street drugs, an Anglo American recession, and the Japanese tech bubble—which put professional-grade musical equipment in reach of any enthusiast—fed musical trends major labels couldn’t anticipate or handle.

The people who could best anticipate and profit from this collision were the legions of young, restless nonconformists who poured into New York in the late ’70s from every corner of the U.S. and the world. Some, like drag performers RuPaul and Lady Bunny, squatted in the abandoned housing scattered about the East and West Village; others, like Monica—a maverick club fiend already working the Chicago punk scene and alt-fashion shows—couch-surfed or split cheap rents with casual friends in cold-water flats on Saint Mark’s Place. As shown in revelatory indie films like Downtown 81 and Wild Style, the Bronx, Harlem, Brooklyn, and the Lower East Side were dystopian wonderlands of crumbling buildings, after-hours clubs, after-work discos, indie bookstores, discount chains, vinyl record shops, and topless go-go bars. A Black-owned WBLS-FM under program director Frankie Crocker was fighting its way to the top of the local ratings by inventing an “urban contemporary format” that played acts as diverse as Melle Mel, Gato Barbieri, Marlena Shaw, Devo, Blondie, the Tom Tom Club, and the Clash. This was the crazy, multicultural city Monica Lynch crashed in 1978 and made her own.

Tell us how you grew up. What was it like being the oldest of six children, living just outside Chicago during the 1960s and ’70s?

At every stage of my life, music was always a big part of it. When I was a kid, I was the one who always monopolized the car radio. When I had to go work with my dad on Saturdays and collect money from his laundromats, I’d be in charge of the dial in the car. I was also listening to all my parents’ music, whether it was the soundtrack to My Fair Lady, or something by the Tijuana Brass. My mother got me one of those early ’60s, mod-looking record players at Korvettes, which I’d play in the basement, and the first album I got was Rubber Soul by the Beatles. I think I really started to self-isolate with music.

Why isolate yourself?

The family situation was pretty chaotic and difficult, but I would go down to the basement and just bury myself in music. I was always going to the local record stores, and I would even go down to the radio station WLS in Marina City in Chicago to watch the jocks spin on air behind the transparent glass. This was still a great golden era for Top 40, and it was that great funky pre-disco period, you know, with the Pointer Sisters and the Average White Band. Chicago was a very important radio town, and radio was still very regional. I did pretty well in grade school, but I left high school early, because I just didn’t want to be there. I managed to squeak by with just enough credits after three and a half years to get a certificate saying that I graduated. Then I started just hanging out and meeting people. The great disco adventure had started, and I began going out with a young group of mostly gay guys. My dear friend Neal Easter and I would go to these small gay clubs like Carol’s, that were really just bars that had small dance floors, and where it was all about the jukebox. Then there was this big, flashy, cool, and glamourous gay disco called the Bistro, run by Eddie Dugan. It was like the Studio 54 of Chicago, and I started going there as much as I possibly could. It was my first time hearing a real club DJ in a DJ booth, and I was completely blown away. The dance floor was pulsing, there were flashing lights and poppers [small bottles of amyl nitrite or butyl nitrite inhaled for euphoric and aphrodisiac effects –Ed.]—I used to love poppers—and it was just that whole thing of being lost in music and dancing.

How did you get involved in the nascent punk scene?

One day, a guy I knew named Noah Boudreau who had a gay club called the Snake Pit, and one of his bartenders, who also managed a local record store called Sounds Good, decided to launch a punk night there called La Mere Vipere (Mother Snake). And I was right in the middle of it. I designed the flyer for the first night, started working there as a bartender, and joined a punk-blues band [B.B. Spin] that would become very popular at the club.

Did you sing?

I wasn’t much of a singer. My friend Steve [Miglio] was the lead singer, and as the only female, I was more like the lead hairdo and glamour-puss of the band. But La Mere Vipere soon became all the rage in Chicago. It got written up all over the place, and while I was still working there and was a habitué of the club, Steve Maas and Anya Phillips and Diego Cortez drove to Chicago in an ambulance to visit La Mere Vipere. Then they went back to New York and opened the Mudd Club as a punk-rock disco. I’m not saying it was just the same, but it’s safe to say it served Steve Maas as one kind of blueprint for the Mudd Club.

When I came to New York on April 24, 1978, it was with a dollar and a dream; although the dream was not particularly well-defined, except that I was bound and determined to go to Studio 54. Officially, I was there to do a runway show for [Chicago designer] Billy Falcon at this cool restaurant in Soho called WPA. But afterwards, I made the snap decision to stay, sleeping on the floor for a couple of nights at a woman’s house near NYU, before moving into a cold-water flat on Saint Mark’s Place with a makeup artist from Chicago. It was the classic late-’70s East Village experience: bathtub in the kitchen, roaches on the floor, hanging out on the stoop waiting for Richard Hell to come by and cop.

You rather quickly encountered all these rising figures on the downtown scene like Klaus Nomi, Joey Arias, Jean-Michel Basquiat, John Lurie, and James Chance.

Anya Phillips, who cofounded the Mudd Club and was the girlfriend/manager of James Chance, lived across the street. She was one of the top-tier movers and shakers of the downtown demimonde. Anya was one of those mythical creatures, a real “it” girl, who kind of scared me because she had such a powerful personality. One day while we were sitting in front of some place on Saint Mark’s, she told me, “You’re going to be a topless dancer. And I’m going to make G-strings for you and sell them to you.” [Suddenly,] we’re flipping through the Village Voice and there’s an ad for the Go-Go Agency. So I go there, and it’s like a scene straight out of Broadway Danny Rose. You walk up to the fifth floor to meet a guy named Angel or Johnny or something. And he shows you the big board up on the wall listing all of the different topless joints for which they booked girls, and the schedule, the list of girls, and all that stuff. So that’s how I started as a topless dancer. I began working for the Go-Go Agency, and they would send me to gigs in all five boroughs. I remember a place in the Bronx called the Slice, the Merry Go Round in Queens, and a bunch of places in Midtown. At the time, there were a lot of punk-rock chicks who danced, because it was an easy way to make a good amount of money and not have to work a straight job.

I guess you would get booked for daytime hours so your nights would be free for going out to clubs, live shows, and networking.

Yes. Some of us would finish our shifts at Show World, then meet up at Fiorucci’s on East Fifty-Ninth Street for cocktail hour to plan what we’d wear that night to Studio 54. When I worked the token-operated “phone booths” at Show World, I went by the name of Mistress Monique, and I would clear $1500 in cash per week. I had a good run there, and it was always hilarious. But in the end, what I realized about these places was that it was all a dead end. This was not a stepping-stone to anything. There were a lot of girls who were having drug issues and who had boyfriends that were sort of pimps. But then again, sometimes you’d meet people who were really interesting. One of the people that I worked with on many occasions at topless places is Wendy O. Williams, who fronted a hard-rock band called the Plasmatics. She was one of the nicest, coolest people, always promoting her music. And she was the first vegan I’d ever met! She even grew her own sprouts in the loft she shared with her boyfriend.

So by 1980, you decided you’d had your fill of the Times Square peep shows and settled into less lucrative straight gigs—until you attended the first New Music Seminar.

By the time I attended the first New Music Seminar, I was already thinking that there might be a future for me in music. I remember hearing a guy there announcing the imminent launch of a music video channel, for cable only, called MTV, and thinking maybe I could get a job there. But about a year later when I saw Tom’s ad for an office manager assistant in the Village Voice and called to apply for it, I didn’t have any idea what it would lead to.

My initial contact with Tom was by phone, and he was pretty tough on me, which I totally understand. I would have been the same way—asking me, “What qualifies you for this?” After all, I hadn’t gone to college, while Tom had gone to a pretty good college. I didn’t have a résumé. My background was sketchy to say the least. I remember having a few initial phone conversations with him, and him really sort of pressuring me. But I guess I did well enough not to eliminate myself completely from the running. Finally, he said, “Well, I’m going out to the pressing plant to pick up our newest release tomorrow. If you want to ride along, we can meet in person.” When we met, he had one of those little hatchback cars and was running the whole operation of Tommy Boy and the magazine Dance Music Report from the second bedroom in his apartment up in Yorkville [on the Upper East Side of Manhattan]. We drove out to Long Island City to this pressing plant called Apexton that was owned by two Polish brothers, to pick up his latest release, which I think might have been “Jazzy Sensation.” And it was truly curbside service. They would use one of those metal hand carts to bring out fifty-count boxes of vinyl 12-inches, then just dump them on the curb, and you had to pick them up. So I just started picking up boxes and slinging them into Tom’s hatchback. At that point, I think Tom decided: “Oh, okay, I think she’s willing to put some back into it.” And that’s how I got started.

What was the full range of your duties?

Answering the phone. Getting records to retailers and record pools. Writing for Dance Music Report. Collecting money from one-stops and record stores. Helping track club and radio play, listening to demos. Visiting clubs and recording studios. Whatever needed to be done!

You were formally employed at a tiny hip-hop label, and reporting for underground DJ tip sheet Dance Music Report. What hot spots did you visit for research?

British expat Ruza Blue, aka Kool Lady Blue, had started a hip-hop night with Fab 5 Freddy at the East Village reggae club Negril, then moved it to a roller disco on the far west side of Chelsea called the Roxy. She’d initially gotten Bambaataa to DJ at Negril, but later at the Roxy she had Bam, Afrika Islam, and Jazzy Jeff all spinning records for her Friday-night parties. These were advertised in the downtown press and attracted large, diverse “uptown meets downtown” crowds. Blue had a great vision to put all that together…and it was Fab 5 Freddy who functioned like an ambassador, bringing a lot of these different worlds together. I was living on the Upper West Side of Manhattan at the time, making it easy to go to the Roxy to hear Bam, Danceteria to hear Mark Kamins, and the Funhouse to hear Jellybean Benitez all in one night. It was a walkable triangle of great clubs with great music. Things were a lot more innocent then. We had a hip-hop world that was Black and Latino, but it also attracted downtown white kids. You also got people from Europe and Japan coming to film this stuff whenever they could. I remember thinking at the time—especially with the Black and Latin kids—that it was a really seamless mix—which, sadly, began to fracture later on.

What about Disco Fever and Harlem World?

I went up to Disco Fever and another Bronx club, the T-Connection, where Bam played. I visited the Fever because it was still hot and still the only place where everybody making moves in the hip-hop world would hang out to share information. I didn’t go to Harlem World much, but the most memorable time I had there was when I stopped by to attend a talent contest. I remember seeing Busy Bee as one of the featured performers, and found myself standing next to another white label owner, Aaron Fuchs [of Tuff City]. Suddenly, just before they were going to award the contest winner his prize, guns started going off, and everybody either hits the floor or is making a mad dash for the door. Aaron, me, and a young girl dove under a staircase. Later, after the place had cleared out, I found out that contest promoters often rigged these noisy disruptions to ensure they wouldn’t have to pay out $500 or $1000 in prize money.

One time, I brought Martin Scorsese up to hear Bam play at the T-Connection. Jay Cox, who was an editor at Newsweek and Tom’s cousin, was good friends with Scorsese; evidently, there’d been some interest expressed on Scorcese’s part, like, “What’s this hip-hop thing that’s happening?” So I organized this night where they got a car and I took them up to T-Connection, where Scorsese watched everything and just sort of took it all in.

In your early years at Tommy Boy, both the synthesizer-heavy sound of electro funk plus the annual New Music Seminars anchored the reputation of your label. What do you think was the cultural impact of the NMS, and how much of your energy and Tommy Boy’s resources went into organizing it?

Well, electro of course was our calling card early on, because we had “Planet Rock,” “Looking for the Perfect Beat,” and “Play at Your Own Risk” and similar singles with Baker & Robie before they started Streetwise, in addition to a string of great electro records from the Jonzun Crew. The electro sound really traveled well, thanks to the Electrifying Mojo on radio in Detroit who opened up the whole Midwest, and Greg Mack at KDAY in L.A. Electro did great in the warm-weather car cultures of Miami and L.A., because it was both melodic and percolating. I mean, you could really hear a car going by playing it. As for the NMS, I think it had an enormous impact on the music industry, especially on people that were just coming up in the business. It became the number one place for networking and showcase performances, and it was designed for new commerce to a large degree. The New Music Seminar coordinated nightly affiliated events, virtually taking over every club in Manhattan. I was drafted each year to put together a few panels, like the independent-label panel and the film-soundtrack panel. This involved sometimes moderating those panels as well as identifying great panelists, reaching them by phone, sending them invitation letters, then making sure they would commit to it. People came from all over the world. Also, all the independent rap labels shared the air and hotel costs of flying Black radio program directors and other important people to participate in the seminar. We collaborated financially so we could take them all to dinner, making sure they could schmooze and have a good time. It made sense, since we were all dealing with the same radio and retail people, and we were all friends with each other. It was a lot easier than having any one of us individually having to shoulder all the costs of courting the same people.

And as the NMS kept getting bigger and better known, it became the model for a number of subsequent music-industry gatherings, such as the CMJ conference, and Florida’s Winter Music conferences.

Yeah. The Seminar was a big rowdy party that was also simply networking writ large. The NMS was particularly important to the history of hip-hop because of the famous MC and DJ battle competitions we hosted. People loved going home from the Seminar telling stories about what happened at specific panels or during the rap battles. One year, Melle Mel lost and ran off with the MC winner’s belt, making the whole audience yell, “The Belt! The Belt!” I’d say we absolutely influenced the CMJ convention, and that many people were looking at the New Music Seminar as a template for industry events to come. But what I think we always did better than anybody else was bring really different worlds and players together. The NMS was a disruptor before the word “disruptor” became a thing.

Nineteen eighty-five was sort of a watershed year for hip-hop. The “Roxanne, Roxanne” answer-record craze crossed a flurry of indie singles to pop radio, Run-DMC’s King of Rock went platinum. Tom Silverman sold half of Tommy Boy to Warner Brothers in a synergistic joint venture, then promoted you to label president after Tommy Boy’s male vocal group the Force M.D.’s scored a top ten pop single, all because you convinced Jam & Lewis to produce “Tender Love” for them for 1985’s Krush Groove movie soundtrack. How did your responsibilities shift as a consequence of being president during the co-venture with Warners?

When the deal happened, I didn’t have any equity in Tommy Boy. But at the time, I was still very much the key liaison person for a number of ongoing things concerning our acts and releases. Basically, we were still an independent label with the vast majority of our releases still coming out through Tommy Boy’s independent distribution network. With crossover acts like the Force M.D.’s or Information Society, Warners would be the gateway for putting out the album, while I would work with Benny Medina and his staff at Warner Brothers coordinating the release of the 12-inch singles. In the mid-’80s, we were not only doing well with the Force M.D.’s, we also had the prestige rap act Stetsasonic, who were highly regarded as producers and who considered themselves the first hip-hop band. I was always discussing our artists with executives in the various departments at Warner Brothers. I’d meet with Black radio or pop promoters, speak with the video department, schmooze with the marketing and the retail side. I’d write and send them marketing plans—which I’m sure were never read.

I’m trying to get a sense of the division of labor. Were you in charge of the day-to-day business of getting records out the door, tracking their commercial progress, and signing acts, while Tom was more in charge of big-picture business affairs issues like supervising label contracts, upper-level management, and bottom-line accounting?

That’s pretty accurate. Tom and I had different roles. But I don’t want to take too much credit for things, because at a small company, people wear a lot of different hats. At Tommy Boy, our structure was fluid, allowing other people to participate in all these different areas as well. I did hire a lot of talented people at Tommy Boy who went on to have great careers both with us and with other labels, and that’s something I’m very proud of. However, Tom was certainly handling all the big business issues and contractual deals with Warner Brothers.

Did you have early signings that immediately convinced you that they and their music could go the distance commercially?

I would say that De La Soul fits that category. Also, Digital Underground, Queen Latifah, House of Pain, and Naughty by Nature. All these artists initially impressed me by virtue of their personal charisma, and/or the fact that their records were just so damn good. De La Soul might be a textbook example of that, and I have pretty good recall of how their deal came about.

Daddy-O, the leader of Stetsasonic, was the person who put me onto De La. Stetsasonic had already been on Tommy Boy for a few years, and they had come to us from the hip-hop radio jock Mr. Magic. Daddy-O, who I knew as Kareem, was very entrepreneurial and would sometimes shop other promising artists he’d discovered. One day, after-hours, he brought me a demo tape of three different acts. He’d already told me over the phone that one of the acts was a young group that Prince Paul was producing whose name was De La Soul. And I remember thinking right away, “What a great, great name! Such a musical and catchy name!” Then he came to the office with the demo tape. I still have it. The first performer was doing mainstream R&B in a sort of Angela Winbush style that I didn’t think Tommy Boy could work successfully. But in the middle of this demo was De La Soul performing “Plug Tunin’ ” and, I think, “Freedom of Speak.” It was so raw and dusted-sounding! Wonderfully distorted. And I was like, wow, these are interesting artists. I wrote up a summary of the three acts for Tom and the business-affairs guy, highlighting the tracks by De La Soul. 

Later, I met with the group in my little office at Tommy Boy, directly across from the bathroom, with no windows. These three guys were so young, they seemed just out of high school. Here they were, coming in from Long Island to see the record company president, and they sat there completely silent for a bit. Then they give me their names: Posdnuos, Trugoy the Dove, and Maseo; I’m like, “Well, what does that mean?” Turns out, Trugoy is “Yogurt” spelled backwards, and Posdnuos is “Sound Sop” backwards. And I start to realize that these guys are on some other shit. Plus, they were dressed differently. They were the antithesis of the leather-jacket, gold-chain, hard-core, Run-DMC–era style.

I still have some of the handwritten things Pos wrote out explaining the D.A.I.S.Y. Age. DAISY was an acronym for Da Inner Sound Y’all. And they had that very enigmatic sample on “Plug Tunin’,” which nobody could recognize, so we ran a popular promotional contest challenging fans to guess the sample. [There was no winner; “Written On the Wall” by the Invitations remained a secret for years. –Ed.]

The elaborate mythology, unorthodox associations, and pop-art graphics developed around De La Soul helped to generate an entire new aesthetic and audience for rap music. And you were creative enough when devising marketing tools and promo swag for the group—like pop-art posters, appropriately quirky videos, and artisanal leather pendants in symbolic revolt against chunky gold chains—to properly support De La’s vision.

I was impressed by De La Soul, because they were radically different. They were speaking in some sort of weird, coded De La language, the raw production was trippy, and they used a slowed-down mystery sample that drove everybody crazy. Plus, at that time in hip-hop, most lyrics were loud, thematically concrete, and outwardly directed rants. These guys were talking about their internal thoughts. There was a cerebral, introverted quality to them in contrast to the dominant sound of the day.

They came across as hip-hop mystics at a time when there was nobody else doing that.

Totally. Shortly thereafter, I hired Dante Ross, a young A&R guy who used to work for Lyor Cohen. The first thing I asked him to do was oversee the recording of the De La Soul album that was being produced by Prince Paul, the Stetsasonic DJ. De La’s first album was a real breakthrough on many fronts.

Everybody who was already in the hip-hop community in New York, from Russell Simmons and Jazzy Jay to Red Alert, immediately loved it, but what happened with 3 Feet High and Rising that helped it really take off was that it was also embraced by white college kids—the proto “backpack rap” audience—who felt a strong connection to it. We’re talking 1988 and 1989, when for a lot of white college kids, De La became their preferred gateway into hip-hop. The use of between-track skits on the album got public attention, and famously, or infamously, so did the sample usages. De La’s first album became sort of a litmus test for the use of samples. We were sued by the Turtles and got cease and desist notices from MCA Publishing for a Steely Dan sample.

Nevertheless, De La Soul had ushered in this very hip period for Tommy Boy, and they were followed pretty quickly by Dana “Queen Latifah” Owens and Digital Underground. We already had the freestyle group TKA who was still rolling along, Stetsasonic was doing well, but then Queen Latifah came into the fold. I always credit three people for bringing her in: Dante Ross, Fab 5 Freddy—who did her early videos—and her producer DJ Mark the 45 King. And she wasn’t “Queen Latifah” at first; she was just Latifah, an eighteen-year-old kid out of New Jersey. Yet Latifah remains one of the most fantastic artists I ever worked with. She was this confident, strong, young female voice at a time when there weren’t many high-profile female rappers.

People tended to lump all female MCs in the same category, although they were each quite different.

I think MC Lyte, who was maybe a year ahead of Latifah, quickly established an alternative aesthetic to battle rappers like Roxanne Shanté, or the sexy, sassy, hook-driven melodic rap of Salt-N-Pepa. I think of MC Lyte and Latifah as stylistic peers, who ushered in a new school of rap for women. Latifah was still a teenager when she started at Tommy Boy, but she had so much poise. When I initially met her at the office, she wore a sweatshirt, jeans, no makeup, and touched up her hair in the bathroom with a curling iron. She had a beautiful speaking voice, and was clearly so down-to-earth, intelligent, and composed, that everyone was immediately struck by her presence. I signed her, and 45 King produced her first single, [1988’s] “Wrath of My Madness” backed with “Princess of the Posse.” Fab 5 Freddy played a significant role in her career, because he did some of her most iconic videos, including “Ladies First.” On stage or screen, she always radiated star power. Latifah also showcased voguing icon Willie Ninja in a video for her hip-house single “Come into My House” the same year Madonna released “Vogue.” De La Soul and Queen Latifah were both part of the Native Tongues movement that started with the Jungle Brothers then expanded to include quirky innovators like Black Sheep and A Tribe Called Quest. Together, this loosely affiliated collective greatly expanded the stylistic possibilities of rap.

You mentioned the importance of Queen Latifah’s videos. I always thought it was very loyal of Tommy Boy to keep making videos for Latifah when her first two albums suffered from lackluster sales.

You know, we weren’t always doing videos for everything at that point. But towards the late 1980s, you not only had Ralph McDaniels and Lionel Martin’s Video Music Box that was a big deal on local TV, you also had Yo! MTV Raps coming on the air nationally. And together with an increase in regional video shows, it became a given that you needed to make videos. Plus, Queen Latifah and De La Soul were incredibly fun projects to work on in terms of their videos. You think about the visual things that people need to connect with an artist. De La Soul’s 3 Feet High and Rising relied on a lot of Afrocentric flower-power psychedelia, while Queen Latifah is shown wearing different types of crowns, then adding quasi military and Pan-African imagery to emphasize her Black female empowerment themes. Rod Houston, who started out as Tom’s assistant, became the video guy. First, he got into club promotion, then he started talking to the mix-show DJs, and when it became apparent that we needed someone to regularly oversee videos—he became that guy. And he did a great job. Because we sought out rising directors who were hungry, resourceful, and in love with each project, our videos were never that expensive to make, certainly not compared to what the major labels were spending.

Did you ever foresee the multimedia career Latifah enjoys now?

After her first single, she went from being Latifah to Queen Latifah. And it was just the most natural progression for her in the world. She’s a self-appointed queen. She says, “I’m Queen Latifah,” and we have to say, “Well, yes—you are!” I still remember when Spike Lee called me looking to give Latifah a speaking part in his 1991 feature Jungle Fever. That became the first of her many film roles. Now she’s got a number one TV show on CBS!

Digital Underground was Tommy Boy’s first big West Coast signing, right?

Yes. D.U. was brought to us from the Bay Area by Ed Strickland, an industry veteran who was doing Black radio promotion for Tommy Boy. One of Ed’s many connections was Atron Gregory, who was Digital Underground’s manager. Atron and Ed gave us the demo tape of the single “Doowutchyalike.” D.U. had previously self-released “Underwater Rhymes” in 1988 through TNT Records, which was named after Atron’s management company.

Shock G, the lead vocalist and visionary cofounder of D.U., just passed away a few months ago. He was a huge jazz and hip-hop fan, and an extraordinarily gifted visual artist. He created all the lettered cartoons and illustrations on the album covers and 12-inches. He had so much humor, imagination, and heart. He came up with the whole idea of [the character] Humpty, as well as the album concept of “sex packets.” You can really see the George Clinton/Pedro Bell/Overton Lloyd influence in his work.

We released the single and video of “Doowutchyalike” in the summer of 1989, and when we followed that up with “The Humpty Dance” in 1990, D.U. completely crossed over… The song and the image of the group went everywhere.

Did you find it interesting that the jolly, playful vibe of D.U. exploded nationally just when the harder sounds of California gangsta rap and Def Jam’s Public Enemy were having a moment?

The success of D.U. was actually the big adrenaline jolt that helped focus everyone’s attention on hip-hop music made outside of the East Coast area. To be fair, there were already two notable East Coast labels that were having success by signing acts out of California and Texas; namely, Profile and Jive. But until regional scenes started producing more national hits, hip-hop remained largely a New York–centered business.

Some might argue that signing one of New York’s most famous Black drag queens to a hip-hop label was counterintuitive. What convinced you that RuPaul’s 1993 album Supermodel of the World could be a hit for Tommy Boy, given hip-hop’s entrenched discomfort with gay culture and gender fluidity?

Well, essentially, this is where you have fun with a capital F. I was contacted by Bill Coleman, who was then the dance-music editor at Billboard, and he told me that [film and video producers] Randy Barbato and Fenton Bailey had contacted him with a demo tape from RuPaul. I said that sounds really interesting, because I knew Lady Bunny and knew that the annual Wigstock drag event was really starting to explode. So I got the cassette, and “Supermodel (You Better Work)” was the track. I met with RuPaul, and thought, “Wow, this is different. This is fun.” It was name-checking all the top models and was a great party/dance record. I thought it could really do something. And Ru in drag is literally larger-than-life…in heels, he towers over everyone. So I said, “Let’s do this!”

Was it the video that helped convince you?

Yes, the video that Randy and Fenton did for the song completely nailed it. If it had just been the track “Supermodel” by RuPaul, but you didn’t have the full visual of RuPaul plus all of the brilliance of the playful scenarios that accompany the track, I don’t think it would have come together. But as an audio/video concept, it seemed the perfect synthesis of the Bryant Park fashion shows and the Wigstock scene that was really blowing up. Therefore, it seemed like a really viable project to do in 1992. Insofar as bringing it to Tommy Boy, I didn’t really consider the fact that internally there might be some negative reactions to the signing. I probably could have anticipated it, because there were hints that some artists were not feeling comfortable with this.

I’ll bet! Do you really think the rap world is comfortable with Frank Ocean and Lil Nas X now?

I’d like to say a lot has changed since 1993, but recent events indicate that there are still a lot of issues there. But I was also struck by a lot of other people telling me, “Wow, that was a bold move. Only you guys would have signed RuPaul.” And I said, “Really? I thought it was a natural.”

How did you promote the single and the following Supermodel of the World album in 1993?

I knew Halston, Todd Oldham, Isaac Mizrahi, Marc Jacobs, and Anna Sui, and all these people were kind of the “it” kids of that generation. You need to remember too that back then, MTV’s House of Style was a very popular program, and supermodel Cindy Crawford was the host. So I just took advantage of the fact it was one of those zeitgeisty moments when fashion, pop culture, the dance community, and the upcoming explosion of the drag scenes, Wigstock, and other things were coming together. And the single “Supermodel” was part of the glue that brought it all together.

The song got used prominently in some of the shows that season. That’s really where it first got played. Then MTV put the video into full-time rotation, and it became a hit. I remember hearing it all the time: “Sashay, chanté!” So fun! But yeah, I know there was an undercurrent coming from the rap world of “Yoooo… What’s up with that!?”

Who brought House of Pain, the Cypress Hill–affiliated white rap group, to Tommy Boy?

Amanda Demme brought us House of Pain. She is a fantastic photographer who was also a force of nature as a party promoter in New York. She was engaged to Ted Demme back then, who was part of Yo! MTV Raps, and I used to hang out with her a bit, socially. She spent time as a door girl at the World in the 1980s, then worked for the New Music Seminar and Sleeping Bag Records for a while before she went to L.A. and started a management company with Happy Walters. Together, they managed both Cypress Hill and House of Pain.

What did you think of the music when you heard it?

I thought it was incredible. Muggs produced the lead single [“Jump Around”] with that crazy intro and a dope backing track that immediately grabbed you. They were coming off the cool factor surrounding Cypress, but that wasn’t all. The lead vocalist Everlast had been on the rap scene for a while, having previously released records under Ice-T’s deal with Warners. But I’ll say one thing about [that] single—it is probably the most-licensed track in Tommy Boy history. It became an anthem that’s been used in countless film trailers and commercials, and it became a big theme song for the Green Bay Packers. It’s one of those tracks that never goes away.

But once again, I think the thing about that record that really hit home was the video. The key element of that video was to have the director, Dave “Shadi” Perez, shoot it at New York’s Saint Patrick’s Day parade.

The way Perez edited the visuals made for a provocative reinterpretation of personal identity and street cred. Quick-cutting between a parade montage and rowdy rap performance footage associated the sober expression of ethnic pride to the Irish bar scene in a way that made you think about bar brawls. And brawls are what half of the song’s lyrics are about.

Perez shot the shit out of that parade. He had a great eye for catching significant micro-moments within the crowd. Then he captures vivid shots of Everlast and his crew looking like typical working-class Irish kids. So you better know that this record jumped off really quick in Boston! After House of Pain, Everlast went on to have enormous success as a solo artist. His solo album, Whitey Ford Sings the Blues, was the last project I gave a green light to at Tommy Boy. It was a big stylistic departure from House of Pain, an acoustic, bluesy kind of record. And it ended up selling more than three million copies.

Why did you walk away from Tommy Boy in early 1998?

It was a combination of factors, in no particular order. I felt completely burnt out. I would take a walk in the park and start envisioning a different life for myself—one where I had gotten off the treadmill. Because I was really working nonstop for all those years. Plus, the hip-hop industry had turned into a whole different game from what it had been when I first encountered it in late 1981.

Did you feel at all discouraged by the rise in CD bootlegging, and the gradual slowing of record sales that would culminate with the advent of Napster and free file-sharing in 1999?

Well, both major and independent labels have always gone through cyclical periods of great success with amazing artists followed by slower periods. And I was still striking gold with compilation ideas [notably the monster-selling ESPN collaboration Jock Jams] and odd, unexpected hit records like Everlast’s Whitey Ford Sings the Blues. But by the mid-1990s, major labels were spending a lot of money to buy into the hip-hop industry. They’d show up with Brinks trucks full of cash and say to the most prolific and talented producer/artists, “We’re going to give you your own imprint.” Suddenly, it became economically far more challenging to be an independent hip-hop label. The Bad Boy era was in full effect, and the whole vibe was changing into something that I just didn’t feel as connected to. I wasn’t having fun anymore. Meanwhile, Tommy Boy had gone from being a small, scrappy, tightly knit label to having over a hundred employees. And alongside all these other concerns, Tom was going through his own evolution and had started a new-age imprint and was giving quite a bit of time and energy to that.

Did you never think about parlaying all your knowledge and expertise and connections into either a Sylvia Rhone–type CEO position at a major label, or a joint venture of your own?

I’ve been asked that many times, and I’ve had more than a few offers from major labels. But to be honest with you, I didn’t feel comfortable in that landscape. There are a lot of politics and rules within major labels, and they are pretty rigid in the way they do things. It didn’t feel like the right fit or vibe for me. At that point, I just felt like I needed to take time off. And I did. Once I left Tommy Boy, I started taking part-time gigs to learn more about music, purely for pleasure. I began working two or three days a week as a stock clerk for a specialty record store called Footlights, helping customers. I auditioned to get a radio show on WFMU, which is a listener-supported, free-form radio station based in Jersey City. I still do occasional fill-in shows for them, and love doing them. So basically, as my friend Irwin always says, I clawed my way to the bottom. And then, last fall, I helped curate the first ever hip-hop memorabilia auction for Sotheby’s. The proceeds from one particularly rare item went completely to an educational charity.

I kind of laugh to myself that I got out of the recording industry while the getting was good. Because between 1999 and 2000, Napster had basically stolen the major label’s lunch money. It’s been said before by people more eloquent than I, that the music industry on the cusp of the twenty-first century was a victim of its own hubris. CDs had been such a cash cow for major labels that they thought they would always be able to dictate the format and mediums on which the public listened to music. They were really caught with their pants down.

And now that music companies seem to have regained some economic equilibrium with the advent of streaming media, do you predict another wave of corporate hubris, or have the multinational juggernauts learned their lesson? Do today’s micro-media platforms and the DIY methods used to make and sell music remind you at all of hip-hop in the early 1980s?

In a way, it is fascinating to see, once again, all these incredibly scrappy, entrepreneurial young people using whatever technology is at hand to lead the charge against all the old top-down business models. There are now so many generations of clever entrepreneurs who’ve come up through hip-hop that they really know what to do. These kids today are so smart, that while looking at recording music as part of the pie, they and their savvy young managers are simultaneously going to move themselves into equity positions in all sorts of businesses, from energy drinks and shares in Lyft to their own cannabis line. And that’s just early career starter moves! It’s gotten incredibly sophisticated with so many purposeful investment strategies, inclusive business models, and forward-looking ways to apply hip-hop hustle. It’s mind-boggling, but that’s the way it is now.