Stribling was born in Markham, Virginia to his parents, Dr. Robert Mackey Stribling and Caroline Clarkson.
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During his 10 years in the House of Delegates, he represented the 18th district, made up of Warren County and parts of Fauquier and Frederick Counties.
At age nine, he moved with his mother and stepfather to Warrenton, Virginia in Fauquier County, Once enrolled in college at George Mason University in Fairfax, Virginia, he began his stand-up comedy career.
It includes the independent cities of Bedford, Charlottesville (main site of the University of Virginia), Danville, as well as portions of three newly added counties Fauquier, Rappahannock and Madison.