He became known for the statues that he populated his grave plot. A Civil War veteran and lifelong bachelor, he was noted for his eccentric behavior. He moved to Graves County, Kentucky after the war and made his fortune as a horse trader.
In 1892 he purchased a large plot at Mayfield's Maplewood Cemetery and surrounded it with 18 statues of himself (including one astride his favorite horse, Fop), his family, a young woman said to have been a childhood sweetheart, and his hunting dogs. The centerpiece is a life-size marble portrait of him atop a tall pedestal, created in Italy; the rest were crafted from limestone by local sculptors.
Wooldridge is the only person actually interred here, in an above-ground vault. The uniqueness of his gravesite has made it a popular example of Americana, and it was named to the United States National Register of Historic Places in 1980. It was also featured on the television show "Ripley's Believe It or Not" and in the film "In Country" (1989), starring Bruce Willis.
In January 2009 the Wooldridge Monuments were seriously damaged when a tree fell on them during an ice storm. Following several months of restoration efforts they were rededicated in October 2010.