Cundey was born in Alhambra, California, United States. As a child, he used to build model sets, suggesting an interest in films from an early age. Cundey already had several low-budget films when he met Debra Hill, who in 1978 recruited him to work on Halloween, a film she co-wrote with Director John Carpenter.

Cundey would go on to work with Carpenter and Hill again on the films The Fog, Escape From New York, The Thing, Halloween II, and Halloween III: Season of the Witch. He would also return to work with Carpenter for the last time on the 1986 big budget science fiction/comedy adventure Big Trouble in Little China. Cundey also served as Director of Photography on the 3D movie "Honey, I Shrunk the Audience!" which ran in five Walt Disney theme parks around the world.

In addition to his work with Carpenter, Cundey would go on to lend his talents for the films Psycho II, Who Framed Roger Rabbit, the Back to the Future trilogy, What Women Want, Apollo 13, Jurassic Park, Romancing the Stone, Roadhouse, and Garfield to name a few. In 1997, he made his directorial debut with the direct-to-video sequel Honey, We Shrunk Ourselves. He recently worked in Canada on Camp Rock, one of several movies that he has filmed outside the United States, including Who Framed Roger Rabbit which was filmed primarily in England. In 2011, Cundey shot the comedy film Jack and Jill, a film which involved extensive split-screen and motion control effects to create the illusion of actor Adam Sandler interacting with multiple on-screen personas.

Cundey is a member of the American Society of Cinematographers. His work on Who Framed Roger Rabbit earned him an Academy Award nomination. On February 2, 2014, he was honored with a Lifetime Achievement Award by The ASC; John Carpenter introduced him.