Esthero was born Jen-Bea Englishman in Ontario, Canada on December 23 1978. When she was 16, Esthero moved from Harriston, the small town where she grew up, to Toronto. Once there she began singing at local open-mic nights and supported herself by working at a variety of jobs - a bakery, a printing house and telemarketing. Manager Beau Ovcaric set up a showcase during that time, and heard her singing at the Free Times Café. He and his partner Zach became her managers, introducing her to EMI Publishing Canada president Michael Mccarty. This got her a recording session with Doc, a guitarist and studio engineer. Their debut album Breath from Another was released in 1998, receiving excellent reviews.

Six years later, on April 20, 2004, she released "O.G. Bitch" an EP featuring six different remixes of the title track plus the song "I Love You." This led the way for the artist's first full-length album on Warner Bros, Wikkid Lil' Grrrls was released. The album won her acclaim, once again, which goes to show that this artist is one who is here for keeps. It hit number 24 on Top Heatseakers in 2004, when it was released. The album also generated the hit single "Fast Lane," which peaked at number five on Hot Dance Music/Club Play and nine on Hot Dance Singles Sales.

Esthero's music has appeared in several films. The movie Go had Esthero and Danny Saber singing the track "Song for Holly" in 1999. For Love and Basketball she recorded the song "Complete Beloved," in 2000. "Every Day is a Holiday (With You)" was recorded for the movie Down With Love in 2003.