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Sherwood Harris Dudley was born on November 4th, 1935 to the late Franklin and Mary Dee Dudley. He was the 2nd of 4 children. He graduated from Schenley High School in Pittsburgh, PA. After high school he joined the Army and was in the 101st Airborne Division and served in the Korean War.
After the military, Sherwood moved Chicago, IL and worked at Mr. Kelly’s Comedy Club. It was there that he caught the eye of Hugh Hefner. Sherwood quickly rose through the ranks at the Playboy Club in Chicago and was instrumental in establishing locations in New York City and Los Angeles becoming the first African American to manage a Playboy Club.
In 1983, Sherwood moved to Portland, OR and worked at Simon’s. From there Sherwood was the head Maitre ‘d at a variety of locations including Couch St. and El Gaucho. For a while he opened his own restaurant called Sherwood’s on the Water.
Sherwood had a knack for making everyone he met feel special, resulting in him being known as the unofficial Mayor of Portland.
Sherwood was proceeded in death by his is older sister, Alma Yvonne “Bonnie” Dudley Pennington, and younger brother Franklin “Buddy” Dudley. He is survived by his twin sister Sherlynn Dudley Reid and his daughter Olivia “Livie” Marie Dudley and a host of nieces, nephews, cousins, family and friends.
Sherwood Harris Dudley will be dearly, deeply, greatly and sorely missed by all.