At the age of 13, Kirkland began making super 8 films and working for his father, noted photographer and filmmaker Douglas Kirkland, creating “making of” films for major production companies. This exposure to Hollywood sparked Kirkland's desire to seek a career in the entertainment industry. Kirkland developed an interest in drawing at an early age. At the age of 17, he began studying in the Experimental Animation Program at the California Institute of the Arts for four years, earning a BFA degree. There, he was mentored by people such as Jules Engel (serving as his teaching assistant), A. Kendall O'Connor, Ollie Johnston and Moe Gollub. In 1976, he won the Student Academy Award for animation along with fellow student, Richard Jefferies, for their graphically animated film made to the song "Fame" by David Bowie. After finishing up his degree, he applied to Disney, but he was not accepted and instead began working for Hanna-Barbera. He began working on The Simpsons from season two onwards and has directed 82 episodes, more than any other director. In season 18, he became the show's supervising director. In 2021, Kirkland left The Simpsons to become supervising director on HouseBroken.
Kirkland has won three Primetime Emmy Awards, two Environmental Media Awards and a Pioneer in Television Animation Award from the Burbank International Film Festival for his work on The Simpsons.
An active member of the Television Academy of Arts and Sciences, Kirkland served as the Animation Peer Group Governor from 2012 to 2013.

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