As Judy Winegrad tells it, the offer to appear on Broadway came with strings attached. If she accepted the role, she would have to break Shabbos. Although Winegard had been dreaming of Broadway longer than she had been keeping Shabbos, she chose Shabbos. It was not an easy decision. She explains, “That meant giving up everything I had and everything I’d known…I realized that if I wanted my will to be Hashem’s will, then I would have to let go. So I let go…And that was hard, because that’s how I defined myself. I defined myself as a performer.” Little did Winegrad know that she was just beginning a career that would make her face – and her voice – recognizable to Jewish women and girls world-wide.
A Lifelong Dream
When we met recently, Winegard told me she had been a shy child. But, “once I got friends or family members in my house…[y]ou had no choice but to buy my ‘ticket’ for my theater production in the living room…if you were familiar, and I was in a familiar place, I was comfortable. I always knew what I wanted to do, but I was paralyzed with fear.”
Her parents, themselves performers, encouraged her singing and acting talents. “My mother brought me to an all-day class at Adelphi University when I was 10 to learn how to confront those fears. It worked!” During high school, Winegrad took classes at Boces Performing Arts and Neighborhood Playhouse in Manhattan and performed with her drama troupe. Later, she attended Ithaca College and received a Bachelor’s in Fine Arts in Drama. She dreamed of a Broadway career and headed for New York City, where she lived for the next few years.
After failing to make a break into the business, and tiring of the hyper-competitive atmosphere of Manhattan, Winegard wanted to try something new. She headed for Los Angeles when someone asked her to sing for the opening of a Russian restaurant. Whenever she met anyone in “the business,” she handed them an audiotape of her singing.
Then the Northridge earthquake struck. “I was living in the Valley, and Studio City – where I lived – was hit pretty hard. My parents were in Israel because my younger sister was about to give birth…Most people didn’t have cell phone at the time, and my sister was living in Shilo. There was no television there. When I finally got them on the phone, and said, ‘Don’t worry! I’m okay,’ they had no idea what I was talking about.
“While I was on the phone telling my parents this, I got a call on the other line. It was Stuart Wax calling. He was a music agent who I’d given one of those tapes of my singing. When I told him I was on the other line with my parents in Israel, he must’ve thought, ‘Here’s a nice Jewish girl,’ because after he arranged a business meeting with me at Pat’s he invited me for Shabbos dinner.”
Wax and his wife lived in a small apartment where they hosted many guests for Shabbos meals. Winegard didn’t attend every week, but she attended often, meeting many Jews in the music and theater scenes. She also found herself increasingly drawn to Yiddishkeit.
Eventually, she got a role as the first understudy for the female lead in “Jekyll and Hyde” while it toured the U.S. “I was pretty miserable. I was trying to hold on. I brought a lot of books on the road with me, but they wouldn’t even let me light Shabbos candles behind stage on Friday night.”
Not long after her return from that tour, she got that offer to perform on stage in New York. Late one Friday night at the the Waxes, in a corner unnoticed by the lively crowd, Winegard chose Shabbos observance over her career.
A Change in Direction
At first, Winegard continued to sing in restaurants because that’s how she paid her bills. She also accompanied a well-known male simcha performer. Soon, though, she met her husband, Laibel.
“Before we married, I told my husband, ‘If I’m talking about covering my hair, how can I keep singing in front of men?'” While Laibel didn’t push her decision, it became harder and harder for Winegard to justify her behavior to herself. After laughing, she told me, “Everything I have taken upon myself, Hashem has sent a test for me. I had just told Laibel, [that I didn’t want to sing in front of men anymore] and Robby Helperin, a good friend who owns Spotlight Music phoned to ask if I’d be his lead singer…and then Peter Himmelman called to ask if I’d perform with him!”
After saying no to these two tempting offers, she received a call from Sarah Weintraub. Weintraub asked Winegard to perform in front of a ladies-only event for Chabad in Santa Monica. “I was hooked,” said Winegard.
Soon, Devorah Kreiman asked her to work with tween and teen students, and then Robin Garbose initiated a collaboration with Winegard that lasts to this day. She has played memorable roles in two of Garbose’s films, A Light for Greytowers and The Heart that Sings, and they co-created a one-woman play called “The Wedding Presence” which Winegard performed in New York. Additionally, she sings for women-only events nationwide and co-directs the yearly musical at Emek.
Not Mere Entertainment
Winegard believes her artistic endeavors are spiritual. “Dovid HaMelech is a singer-songwriter. Song is the combination of words, music, and neshama together. It’s pure.”
Winegard has sung for family members in their final moments and for friends in the depths of depression. To both groups, she transmitted messages of comfort and emunah. Even her movies – which some might label “mere entertainment” – convey hope, optimism, and a Jewish world view. “So many people are feeling desperate, without hope,” she explained to me. “Song is a life raft.”
When she uses music in this way, it becomes holy. “It doesn’t matter whether I’m singing in front of two hundred people, a thousand, or just ten women. Each performance is different. Women are touched. They come to me later, crying. There’s an electric connection, soul to soul.”
The opening act for Moshiach…on the women’s side
Right now, Winegard is preparing the students at Emek for their upcoming musical, a “Best of Broadway” review containing music written by Jewish composers. Her next album will be released soon and includes a song with lyrics by Devorah Kreiman. Winegard also very much hopes to stage “The Wedding Presence” on the West Coast. “I would like to continue to inspire frum Jewish women, but also all klal Yisroel, all Jewish women.”
Once, Winegard found herself singing in front of musician Naftali Finkel, who does the sound on most of her projects. (Because of his technical role, he is permitted to hear her sing.) “How could you give THAT up?” he asked.
Winegard said, “What are you talking about? I’m going to be the opening act for Moshiach…on the Women’s Side!”