Darrell Brewster got his start playing football and basketball at Portland High School. In 1948 he was named Indiana High School Basketball All Star. After high school, He went to Purdue University, located in West Lafayette, Indiana, on a basketball scholarship. While at Purdue, he also played Varsity football on the 1952 College Football All Star Team. Brewster went on to play nine seasons in the NFL. He earned two NFL championships with the Cleveland Browns in 1954 and 1955. During that time he also accumulated 210 receptions, 3,758 receiving yards, and 21 touchdowns as an offensive end. After his playing career ended in 1960, Brewster was a receivers coach with the Kansas City Chiefs and the Minnesota Vikings, earning a Super Bowl ring with the Chiefs in Super Bowl IV.
Brewster is enshrined in the Indiana Football Hall of Fame and the football field at East Jay Middle School has been dedicated in his name. In 2007 he was inducted into the Purdue Athletic Hall of Fame.
After retiring from football, he lived in Peculiar, Missouri on the outskirts of Kansas City for many years, until his death in 2020.