Kenny Pearl began dance studies with David Earle and Patricia Beatty, and at the National Ballet School. After graduating from the University of Toronto he went to New York to dance, and stayed for thirteen years. He toured internationally with the Alvin Ailey American Dance Theater, danced independently, and with the Martha Graham Dance Company. He studied acting, performed comedy cabaret, and after his 1981 return to Canada, spent a season at the Stratford Festival. He has taught at the Martha Graham School, the Juilliard School, the Ailey School, and at the New York High School of Performing Arts. A frequent guest teacher in Vancouver, he has also taught in Montreal and Quebec City, and since 2002, has taught the graduating class in the dance program at Ryerson University. He was the Artistic Director of the School of TDT in 1991 and 1992, and taught in the School for the next decade.

Kenny Pearl was TDT’s Artistic Director from 1983-1987, beginning at a very challenging time. Through his leadership financial stability was restored and the company’s artistic profile was raised through successful international touring. His distinctive artistic vision nurtured TDT’s highly talented dancers, including Karen Duplisea and Grace Miyagawa, and promoted the work of Christopher House alongside the founders. David Earle's major works Sunrise and Sacra Conversazione were created during his directorship, and Christopher House's work blossomed. Kenny Pearl co-directed David Earle’s Court of Miracles for ten years of annual Toronto presentations, and at the River Run Centre in Guelph, Ontario in December 2003, celebrating the twentieth anniversary of its creation.