Cummings was born and raised in the Canadian city of Winnipeg as were all of the original members of "The Guess Who".
Cummings ultimately made the move to Sherman Oaks California and began writing and singing for films in the late 1970's. He currently Winters in California and returns to Winnipeg in the Summer, living in Canada through the Autumn. He co-starred in the movie "Melanie".
In 2000, Cummings, Bachman and original drummer Garry Peterson toured as The Guess Who. Bassist Jim Kale played one show and former Guess Who sidemen Donnie McDougall and Bill Wallace re-joined the line-up through the remainder of the tour in Canada and later in the U.S.