Hogestyn began his acting career by entering a Columbia Pictures talent search that included 75,000 people. Hogestyn was among the 30 selected, and his first starring role was on the prime time series Seven Brides for Seven Brothers. After a few minor roles (one as Kort, leader of the Micro Workers in the episode 'Princess Metra', on the 80s television series Otherworld (TV series)), Hogestyn joined the cast of Days of our Lives in 1986. He initially played a mystery man referred to simply as "The Pawn," however, it was soon revealed The Pawn was the presumed dead Roman Brady. Hogestyn quickly became a fan favorite and enjoyed many popular pairings, the most popular of which was the legendary one he shared with longtime co-star Deidre Hall. In 1998, while starring on Days, Shelley Long wanted Drake to join her for an upcoming series, Kelly, Kelly. He was set to star in both until the filming of the pilot episode of Kelly, Kelly conflicted with his schedule on Days and the role went to Robert Hays.