The Parkside Lounge, in lower Manhattan, is not the most elegant place on earth. The dark walls are dotted with faded covers of Life magazine. The floors are sticky with beer, the bathrooms uninviting. A jukebox blasts music loud enough to quell the conversations of a swelling crowd of young hipsters. In the back, where high-profile industry showcases take place, the stage is decorated with long, luminescent strips of plastic, eerily reminiscent of the prom scene in Carrie. Standing in front of the stage, pouring herbal tea from an unplugged pot, is Grammy-nominated, progressive-soul singer Maiysha Simpson ’97. (Professionally, she goes by her first name only.) Maiysha is fighting a cold—not a good thing when you have an important performance in an hour. People from her management and record companies are coming down tonight. Former Sony Music chief Don Ienner sits ringside. And the jaded hipsters from the front room will soon be back here, demanding to be impressed. But she seems unfazed.
Maiysha abandoned a lucrative modeling career in order to sing at the Parkside Lounge tonight. Which, while not Webster Hall, is still an important spot. A folk singer Ienner has signed to his new label will also showcase some songs tonight, and it’s clear that, aside from the funky bathrooms, this is a place where careers take flight.
Maiysha grew up in a music-filled home in Minneapolis. Her parents “listened to everything from Joni Mitchell and Billie Holiday to Natalie Cole and all the Motown greats, like Martha Reeves and Diana Ross,” she remembers. “I think this accounts for my eclectic tastes.” (Her first album, This Much Is True, has everything from traditional R&B to a country-blues take on Peter Gabriel’s “Sledgehammer.”)
Maiysha started performing in musical theatre at age 7, but says, “I didn’t take myself seriously as a singer until I started studying voice at Sarah Lawrence,” where she also studied creative writing. In a class with Dave McCree, she learned a naturalistic singing style that now separates her from the current crop of showy, American Idol-style singers.
“I learned how not to overdo it in Dave’s workshop. His main thing was, ‘serve the song.’ If you stick to telling the song’s story, you really will become a better vocalist.”
After graduation, Maiysha started working as a model for the prestigious Ford modeling agency. “Some people waited tables to pay the bills after college. I modeled!” She enjoyed singing live with a band, but didn’t know what sort of music to concentrate on. “We did a little bit of everything, but the unstructured aspect of the group didn’t really suit my needs.” Good fortune came to her, ironically, at a 9/11 benefit in New York some eight years ago.
“Some mutual friends introduced me to a guy named Scott Jacoby, who was also playing that night. Once we got to talking, I realized that Scott and I were on the same wavelength. He suggested I come to his studio and try writing with him. I went to see him with lyric ideas and snatches of melody and he knew exactly the kinds of chord changes and grooves to set my songs to.” They worked together to create the songs on This Much Is True, and Maiysha felt she was finally on to something.
But finding the right writing partner and producer was only half the battle. When she approached the major record labels for a deal, “It was a pretty rude awakening.” Despite her prodigious talent and stunning looks, “A lot of executives said straight out that they weren’t looking to sign any female over the age of 25!” The double standard irked her—“A guy can pretty much look any way he wants and be over 30, but a girl can’t. It’s absurd.”
So Maiysha released This Much Is True on Jacoby’s small label, Eusonia. The album was quickly hailed as a breakthrough by Ebony, Newsweek, Entertainment Weekly, and other national magazines. Then her single, “Wanna Be,” was nominated for the Grammy Award for best female vocal performance.
Singing full-time has its drawbacks, though— including a pay cut. Not only did she finance her first album almost singlehandedly, but the time spent writing, recording, and gigging left no time for her very lucrative modeling career. The change in economic status was humbling.
“When I modeled, it was all pretty easy. The money is good, you travel and meet all kinds of exciting people. So, it’s been something of a shock to try and become a full-time singer. My apartment was well within my budget as a model, but it’s a struggle to maintain as a musician. So, it’s been a big sacrifice, going from prosperous model to starving singer.
“Still, so far, it’s been worth it. Certainly getting the Grammy nod and being able to go to the awards ceremony and see some of my idols, like Cassandra Wilson, made me feel I was on the right track.”
When asked if there were any other differences between being a silent, smiling model and singing on a stage, Maiysha’s answer betrays her consistently striking honesty.
“In some ways there’s no difference at all,” she says. “You’re in a pretty vulnerable position in both jobs. Basically, whether you’re strutting on the catwalk or singing, people are staring at you and judging you. At least with my songs, I can give people my ideas and point of view. I’m in control. I decide what to write, what to sing, what to wear, and how to present myself onstage.”
The singer also doesn’t flinch at the question of how important stardom is. “I have my priorities pretty straight,” Maiysha says. “I certainly wouldn’t mind if I became a star. But that’s not really a good goal. Stars can’t leave their houses or walk down the street. I like living in New York and being anonymous.
“Really, what I’m looking for, aside from making a living, is validation. I think about some of the people I admire, like Cassandra Wilson. They’re respected. Respect by ones’ peers is a healthy goal. It means that what you’re doing is musically valid.”
At the Parkside Lounge, Maiysha excuses herself after having downed multiple cups of tea.
“It’s been a stressful week,” she says. “Lots of rehearsals and running around and now I’ve got this cold. I have to eat something. I’m feeling a bit shakey.”
Whatever she eats should be on the table of every up-and-coming pop star. For, an hour later, a remarkable transformation takes place on the Parkside stage, with the colorful Carrie-like backdrop.
The singer starts out, almost tentatively, with “This Much Is True,” the title track of her most recent CD, backed only by a dreadlocked acoustic guitar player. Her voice is soulful, quiet, almost husky. Suddenly she lets go with a gospel-style roar that could rattle the fillings of Chaka Khan. The beautiful people in the dark respond by shrieking like congregants in a Pentecostal church. From this point on, Maiysha has them in the pocket of her jeans. With each song she grows looser and stronger, in direct contrast to the slightly weary, congested beauty that was speaking only an hour before. Cold and all, Maiysha has made another crowd of blasé New Yorkers stomp and clap like true believers.
Peter Gerstenzang is an award-winning humorist. His work has appeared in The New York Times, SPIN, The Saturday Evening Post, and many others.
+ Maiysha kicked off the school year with a speech to incoming students. Watch the video»