Buckley was born in Salem, Massachusetts, the son of Barbara J. (King) and Andrew P. Buckley. He has two brothers and a sister. He attended Pine Crest School, where he graduated in 1983, and Stanford University, where he graduated in 1987 with a bachelor's degree in political science. He played golf on the Stanford Men's Golf Team. He later studied sketch comedy and improvisation at the Groundlings Theatre, working with comedians Melissa McCarthy and Dax Shepard.
Buckley appeared in two 1997 music videos, "I'd Rather Ride Around with You" and "What if it's You", by country music artist Reba McEntire.
Buckley played David Wallace, embattled CFO and later CEO of the fictional Dunder Mifflin Paper Company, in 37 episodes of The Office from 2006 to 2013. At the time of his initial appearance, he had been working as a financial advisor at Merrill Lynch, and had been cast specifically because of his familiarity with the world of corporate finance. He continued to work in the finance industry full-time during his recurring role on The Office.

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