|First Sunny Boy Sam in color, 8/19/50|
Wilbert Louie Holloway was born in Indiana on August 11, 1899, according to his World War I draft card. In the 1900 U.S. Federal Census, he was the only child of John and Lucy, who lived in Jeffersonville, Indiana. His father was a day laborer.
In 1910, the family remained in the same city where he was the oldest of three children. His father was involved in car work. The date of their move to Indianapolis, Indiana is not known. Holloway signed his World War I draft card on September 12, 1918. His address was 1413 East 16th in Indianapolis, and attended the Indianapolis Technical Institute. His description was medium height and build with brown eyes and black hair.
Holloway, his father and brother Neely were recorded in the 1920 census. They lived in Indianapolis, Indiana at 1413 East 16 Street. His father had divorced and worked at a brass foundry. His brother was employed at a meat packing company. He was unemployed. At Ancestry.com, the Indiana Marriage Collection recorded Holloway’s marriage, on June 12, 1922, to Fannie Belle Smith. In Hale Woodruff: 50 Years of His Art (1979), “Woodruff shared a small studio with Wilbert Holloway who also had attended the Herron Art School.” In Notable Black American Men: Volume 1 (1998), Jessie Carney Smith wrote about artist Hale Woodruff, and said he was “…Sharing evening studio expenses with artists Wilbert Holloway (who was the only other African American student in the class of about 40 students at Herron) and John Wesley Hardrick…” From an interview in Hale Woodruff: 50 Years of His Art, Woodruff recalled his time with Holloway.
Wilbert Holloway, who was a cartoonist for the “Pittsburgh “Courier,” and I went to art school together. We had a funny little studio together back in Indianapolis in the early 1920’s. One day he said, “Man, this fine art is too much for me. I’m going to get into something where I can deal with the people.” So he wrote to Mr. Robert L. Vann, who was editor of the “Courier” in Pittsburgh, and got a job that paid him $50 a week as cartoonist.
The date of his move to Pittsburgh, Pennsylvania is not known. In 1928, his strip Sunny Boy Sam began in the Courier.
In the 1930 census, he, Fannie and two daughters lived in Pittsburgh at 1238 Monticello Street. A Black National News Service: The Associated Negro Press and Claude Barnett, 1919-1945 (1984) published this account of Holloway’s attempt to get his strip syndicated.
In January 1930, Wilbert Holloway, who was drawing “Sunny Boy Sam” for the Pittsburgh Courier, wrote the director asking if ANP [Associated Negro Press] could handle “my strip which embodies clean, wholesome humor.” While lauding the imagination and execution of the strip, Barnett turned down Holloway’s proposal. “For some time we have been attempting to work out a plan whereby we might syndicate cartoons and pictures. Thus far we have not been successful. The papers have not shown an interest. We shall continue our efforts and if we succeed, you shall be one of the first we will contact.”
With America’s entry into World War II, the January 31, 1942 issue of the Courier printed a letter to the editor from James C. Thompson of Wichita, Kansas. The letter was reprinted in the April 11, 1942 issue. Staff artist Holloway’s contribution was described at America’s History in the Making.
The Pittsburgh Courier‘s “Double V” idea, created in the mind of James G. Thompson of Wichita, Kansas, and brought to glowing light through the brilliant pen of Wilbert L. Holloway, Courier staff artist, has swept the nation like wildfire.
An image of the Double V is at Double Victory Campaign. Weeds: An Environmental History of Metropolitan America (2011) reprinted one of his editorial cartoons from 1943.