Hogestyn was born in Fort Wayne, Indiana, where he graduated from North Side High School. He attended the University of South Florida in Tampa on a baseball scholarship, majoring in pre-dentistry. He graduated with a double major in microbiology and applied sciences. He was then drafted by two professional baseball organizations: the St. Louis Cardinals and the New York Yankees. Hogestyn signed with the Yankees and played third base for one of their farm teams until he was injured in 1978.
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.
In 1991, Wayne Northrop agreed to return to Days to reprise his role of Roman. In order to keep both actors on the show, Drake's story was retconned and his past rewritten. Despite this change, Hogestyn remained one of the show's most popular actors. The pairing of John Black and Marlena Evans (Deidre Hall) is one of the show's enduring super-couples.
Drake's John Black character was "killed off" the week of October 15, 2007. It was rumored the character was officially dead and would not be back, but Days has a reputation for "killing" many characters and eventually bringing them back. In fact it turned out that John was not really dead at all, but had been abducted by long-time nemesis Stefano DiMera. As of January 8, 2008, Drake was back on Days of our Lives in the role he created. Confirmed on November 17, 2008, Drake, along with his long-time co-star, Deidre Hall, were let go from Days of our Lives due to budget cuts. It has recently been revealed that Days of Our Lives is bringing back the characters of John and Marlena starting September 26, 2011.
Hogestyn married his childhood sweetheart Victoria. The couple have four children: three daughters, Whitney, Alexandra and Rachael; and one stepson, Ben. Drake Hogestyn is a practitioner of Bruce Lee's Jeet Kune Do as is his Days Of Our Lives character John Black (Days of Our Lives). In real life Bruce Lee is one of Hogestyn's idols & is a master of the Nunchaku the weapon that Lee was known for using in his films.