By Ben Joravsky

On the day before her CD-release party, jazz diva Pippi is sitting in a Mexican restaurant on Wells Street, sipping a margarita, talking on a cell phone, and trying not to lose her mind. Her designer is on the line, and he’s stuck in Dallas along with the dress she was expecting to wear at the party.

The previous call, from her CD manufacturer, was even worse. The 5,000 copies of Black Coffee, her self-produced collection of standards that she was planning to sell at the door? Well, there’s been some sort of mix-up, and only 500 will be available.

“I’m gonna stay cool–I’m not gonna trip,” she says as she shuts off the phone. “This is going to work. I believe. I have faith.”

It’s been this way for almost nine months now, as she’s cleared one obstacle after another in her effort to produce, promote, and sell her own CD out of Chicago. “I plan to sell ten million copies of Black Coffee,” she says. “Don’t tell me it can’t be done–it will happen.”

It’s hard to think of Pippi as an overnight sensation, since she’s been singing jazz at nightclubs around town for almost 30 years. She’s a south-sider by birth, the oldest of eight children who grew up in Woodlawn. Her father, Harold Eugene McDowell, was a businessman; her mother, Ruth Bernstein McDowell, was a beautician. Pippi’s real name is Ardennia; she says, “I got the nickname Pippi because as a baby in the crib I used to squeak and they called me pip-squeak.” From an early age it was clear that she was meant to be a singer. “I sang in my grandfather’s church at 61st and Indiana. I’ll never forget the first time my grandfather let me sing. It was ‘I’m a Solider in the Army of the Lord.’ I was eight years old. I’m singing that song, and the people are just loving it. This was a Pentecostal church. They were real Holy Rollers, and they were feeding off the spirit.”

By the age of 13 she was singing doo-wop in various south-side clubs. “My mother set it up,” says Pippi. “She was a real entrepreneur. She used to take me around–the High Chaparral, the Burning Spear. I was singing with three guys behind me, friends from the neighborhood. We used to rehearse on the porch. This is, what, 1967, and I’m underage, so my mother would bring me in and take me out. I got $50 a night, and we had ourselves some fun.”

In 1970 she graduated from high school, a private alternative school called Broadmoor Academy. “I graduated at age 16–I was always moving fast,” she says. “I got married at age 17. He was a musician, Robert Fentress. We got married in City Hall. He wasn’t but 17 either. My father had a pizza place back then, at 51st and Lake Park. And Robert walked in one day with a bag on his arm filled with music paper. He said, ‘I’d like to have a cheeseburger with mayonnaise and no onions.’ I said, ‘How can you have a cheeseburger with mayo and no onions? If you like mayo you ought to have onions.’ I was fascinated by the fact that he didn’t like onions, so I invited him to a housewarming party I was having to celebrate this one-room place I was moving into over on Cornell in Hyde Park. Well, he came to the party, and he never left. I fell in love with him. My parents didn’t really like that. I remember once my dad came over unexpectedly, and I told Robert to go hide in the closet. I thought my dad was just stopping by, but he stayed a while. He had me cook him some steaks, and he started this real long conversation, and he was acting like he had nowhere to go. Finally he got up, kissed me good-bye, walked to the door, turned, and said, ‘You can come out of the closet now, Robert.'”

In those days Pippi sang and Robert accompanied her on piano. Her style then, as now, drew its strength from her emotion, from her spirit. “I could always find work,” she says. “People always responded. They’d tell me, ‘Girl, you can sing.’ Robert and I moved to Hollywood for a while to get our music careers started. We went out to Capitol Records and to A&M. They said our music was too positive–whatever that means–and nothing came of it. So we came back to Chicago. We lived on the north side, around Old Town. I loved that energy. I was a real hippie girl. It was a time, a real trip. You name it, I tried it. I even did some topless go-go dancing. Why not? The money was good–$700 a week. It was at a club called the Midas Touch on Wells Street. They treated me so good. They were very protective. Some of the other girls kept going upstairs with the men customers, but the owners wouldn’t let anyone approach me, not even to buy me a drink.”

She and Robert moved to a loft at 1361 N. Wells. “It was basically a musicians’ building. There was a classical musician on the first floor and a rock musician on the third. In our apartment we had an electric piano and microphone all set up. We’d hold jam sessions. Musicians would come over and perform and hang out. I’d make these incredible spinach salads. It was great. I used to sit on the fire escape and look down on Wells Street. The things I saw–it was an education. There was this gay nightclub across the street, and I used to watch some of the finest women walk out of the club. Only they were men dressed like women. They’d get into cars of men who were cruising, looking for action. I’d see them get into the cars at the southeast corner of Wells and Schiller, and by the time they got to the northeast corner they were out of the cars.”

She sang at clubs in and around the Gold Coast and Old Town throughout the 70s. By the mid-1980s she needed a change. She and Robert, who’d had two children, divorced. Then, she says, “I needed money for my children. I had to get a so-called real job. I was tired of singing clubs. It’s a hard life. I was doing some 60 songs a night and working from 9 to 3:30.”

She took several courses in computer technology and worked as a programmer and trainer. She got involved in local politics and made lots of north-side contacts. She worked as executive director of the Old Town Chamber of Commerce and with the city’s Department of Human Services and the Chicago Housing Authority. “When I was young I had this dream I was going to be a star–that someone would walk into the club and hear me sing and give me that contract,” she says. “But it never happened that way. In some ways I was really lucky. It was a blessing for my family. Because in that culture and at that time–with drugs being what they were and me being the kind of spirit I was, always trying something–well, I would have tried something that would have either killed me or hooked me up. I never really stopped singing though. I always booked my own stuff. I played with Lloyd Wilson on piano. The man’s fantastic. But I wasn’t giving much thought to my musical future.”

Then one day last summer she was singing at a local restaurant. “After the performance one of my neighbors came up to me and asked if I wanted to be rich and famous,” she says. “I told him that at this particular time it didn’t make any difference if I was famous, but I wanted to be rich to take care of my kids. He said, ‘Just give me a CD of all the music that you’ve been playing tonight, and I’ll help you make yourself rich.'”

It turned out that the neighbor, Todd Rosenbaum, owned Top Hits Distribution, a local company that, as Pippi puts it, “puts CDs in nontraditional places like Walgreens. He got me thinking–why not cut a CD? Why not get it done?”

It wasn’t going to be easy. Many people are skeptical bordering on scornful of independent productions, particularly records and books. “I know the trip–‘If you’re so good, how come some big company’s not backing you?'” Pippi says. “People have got to understand that going with a major label’s not all it seems. In the 1980s I was presented with two recording contracts that I turned down. They were talking about taking 50 percent of my publishing rights and paying me and my husband 13 cents an album. To me, it didn’t make any freaking sense. These people want to own it all, to bleed you dry. In any venture there’s going to be debt and profit. You’re a player or you’re being played. That’s just the way it is. Aretha Franklin said it best–‘Who’s zooming who?’ But a lot of performers are so hungry for success they’ll sign on.”

In October she rented studio time at Chicago Recording Company. She called Wilson, who brought in the other musicians: Bobby Broom on guitar, Toby Williams on drums, Donald Jackson on bass, and Ahmad Salaheldeen on saxophone. She picked ten songs, including a soulful rendition of James Taylor’s “Fire and Rain.” She sang the title tune with a rueful smile. “It’s been around for a while, ‘Black Coffee,'” she says. “It was written by J. Francis Burke and Paul Francis Webster. I loved it. Always have. Lloyd and I have been playing it for years. We do it up-tempo. ‘I’m feeling kinda lonesome / I haven’t slept a wink / I walk the floor and watch the door / And in between I drink black coffee / Love’s hand-me-down brew / I’ll never know a Sunday in this weekday mood.’ I love the refrain: ‘A man was born to go a-lovin’ / A woman to weep and fret / And stay at home and tend her oven / And drown her regrets in coffee and cigarettes.’ Wow. We did it in one take.”

By May the CD was completed and the package designed. She booked the Black Orchid, a club at North and Wells, for a CD-release party. She hired a computer programmer, Tyrone Wilson of Wilson Systems, to design a Web site. She hooked up with WVON DJ and radio commercial maker Richard Pegue, and he recorded the voice-over for her Web site. By this point she’d spent thousands of dollars, much of it borrowed.

Pegue suggested that she come to the Friday-night dance party he and WBEZ jazz DJ Richard Steele hold every Friday night at Taste Entertain-ment, a nightclub at 63rd and Lowe. On June 23 she drove down. Pegue put on her record, and the crowd of steppers got into it. “Who is this?” asked one dancer. “Nancy Wilson?”

“No, the lady’s in the house,” said Steele. He called her to the stage. Pegue put on “Black Coffee” and all of a sudden the crowd was calling for her to sing. So Pippi took the mike and sang along with the music, and the audience–some 60 or so R & B devotees–went wild. They were swinging and clapping and calling her name. Someone ran onstage to press a dollar bill into her hand. Then another person followed, and another and another. Almost 40 in all, until she, still singing, held a fistful of dollars. When she finished, the crowd rushed around her. They hugged her, begged for autographs, promised to attend her July 12 CD-release party and to buy Black Coffee. “A lot of people can relate,” says Steele. “A lot of people feel they have great talents buried within. They want her to succeed.”


As the hours tick down to the July 12 party, things go from hopeless–few CDs, no dress–to OK. Pippi’s designer, a south-sider named Haj, catches another plane out of Dallas and does the final fitting a few hours before the show. But only 500 CDs are delivered.

On the day of the show her daughter and nieces skip about her as she puts on an outrageously large Afro wig. “I always wear wigs,” she says. “It beats a bad hair day anytime.” She then drives to the Black Orchid with Houston Day, her 12-year-old nephew, and they run around the club, hanging up posters, arranging the appetizer plate, and taking care of other last-minute details. By 7:30 the room is packed with close to 400 people.

Pippi and her daughter and some of Pippi’s women friends gather in a basement dressing room. The room fills with smoke and nervous laughter and the sound of ice cubes clinking in glasses. At 7:45 Lloyd Wilson and Pippi go over the playlist.

Then Houston and his sisters burst in. “Aunt Pippi, you gotta get on. People are waiting.”

Pippi adjusts her dress, checks herself in the mirror, takes off the Afro wig and puts on a wig with more curls, then walks down the corridor past large framed photos of stars such as Nat King Cole and Ramsey Lewis and Will Robinson.

Richard Steele is waiting for her in the wings of the stage. “You OK?” he asks.

“Ready,” she says.

“Let’s go then.”

He walks onstage and tells the audience, “She grew up singing in a church. Sometimes record companies just don’t get it–they just don’t hear it. I want you to give her all the love you can muster–the fantastic Pippi.”

Pippi seems a little nervous, rushing a bit through her first song. Then she settles down, calling out to friends and old acquaintances. As the band plays the first chords of “Fire and Rain,” she talks about her life. “Being a woman over 40–plus–I decided I’d do the last half the way I wanted.” The crowd cheers.

She closes with “Black Coffee.” She gets a standing ovation. Her encore is “Stormy Monday.”

“‘Fire and Rain’ didn’t work so well for me,” says one fan afterward. “I think she ought to stick with the up-tempo tunes which highlight her personality.”

“No, no,” another fan says. “‘Fire and Rain’ is just the sort of thing that will go over huge on WNUA.”

“She has talent–no question about that,” says Steele. “That scene at Taste was key. I mean, a lot of people here are her friends. They love her stuff already. But the crowd at Taste can be tough. And they loved her. She connected. It was real. I know it’s a long shot, but I think she might pull it off. Black Coffee could be number one on the jazz charts. Sometimes artists in Chicago are not appreciated like they should be. Then they go out there and hit it big. Chicago’s just a little tough. I don’t know why that is.”

The next day Pippi is back working the phones. “We’re calling the record stores, checking out the radio stations,” she says. “Everything has been put in place by divine order. I’m feeling particularly blessed. I believe it’s going to happen–ten million copies–just like I said.” o

Art accompanying story in printed newspaper (not available in this archive): Pippi photo by Jon Randolph.