Deborah Claire Wesoff-Kowalski, better known as Debbie Deb is an American singer, best known for 1980s freestyle dance songs such as “Lookout Weekend” and “When I Hear Music”.
Deb was born in Brooklyn, New York, and raised in North Miami Beach, Florida. A music aficionado from a young age, she was “discovered” at the age of 16 by producer Pretty Tony at a Miami record store where she was working. While Debbie had no formal training in singing, she had been singing most of her life. Pretty Tony told her that he liked the way she spoke and asked if she could sing, and she answered yes. They recorded “When I Hear Music,” which she co-wrote with Pretty Tony in his studio the very next day. Released on the Jam Packed record label in 1984, the song has since become a staple in clubs and on dance and urban radio stations and mixshows. Other hits followed, including “Lookout Weekend”, “I Wanna Work It Out”, “There’s A Party Going On”, “I Wanna Dance,” and a remake of Connie’s 1980s Latin freestyle classic “Funky Little Beat”.
A CD called “Lookout Weekend” appeared on the market under Debbie Deb’s name. It included “When I Hear Music”, “Lookout Weekend”, “I’m Searchin'” and “Fantasy”. “I’m Searchin'” went on to become a club and radio hit, but features another vocalist on the lead, recording that song and “Fantasy” as “Debbie Deb”. The cover of the CD featured a drawing of “Debbie”, however, Deb was overweight and suffered from low self-esteem, and found her sudden fame difficult to cope with. She was crushed when her record company decided not to put her picture on the sleeves of her records and, in a Milli Vanilli-esque move, even hired an “impostor” to perform and pose as “Debbie Deb”. As a result, she made little, if any, money from her hit singles, and was so hurt by the experience that she stopped singing for years, relying on her work as a hairdresser to make ends meet.
Deb finally resurfaced on the recording scene in 1995 with the album She’s Back. Now living in New Port Richey, Florida, she continues to stay busy performing frequent concerts around the United States, especially “freestyle revival” shows with other artists like Lisa Lisa, Stevie B, Exposé, The Cover Girls, and Shannon. Gwen Stefani and Jonathan Davis of Korn have cited Deb as an influence, and in the summer of 2006, Janet Jackson featured a cover version of “Lookout Weekend” on her Web site.
In 2009, Debbie debuted a new single, “Everytime You Come Around,” on her Myspace page (on which she bills herself as “The Real Debbie Deb”).
In 2015 Debbie rerecorded a new version of “Lookout Weekend” with electro-house artist Reid Stefan.