Drew grew up in Lebanon, Indiana, outside of Indianapolis. He graduated from DePauw University, where he majored in English Literature and was a Media Fellow, an honors program in media studies. He was active in the theatre department, and wrote and performed in campus television shows and student films.
After graduation, Drew moved to Los Angeles. His first television appearance was a small co-starring role in the hit television series Malcolm in the Middle. So impressed were the producers of the show that they wrote the role into episode after episode and even named the character after him: Cadet Drew. He appeared on many episodes of the show over two seasons.
Next up for Drew was the prequel to Bonanza called The Ponderosa on which he played Hoss Cartwright. The twenty episodes produced continue to air on cable. Shooting in rural Australia, Drew met and fell in love with Veronica, now his wife, who was a make-up artist on the show.
Drew‘s first starring role in a major feature film is in the remake of the 1971 film Straw Dogs, directed by Rod Lurie. Other feature film appearances include Starship Troopers 2, The Marine, Mexican Sunrise and 1408 with John Cusack and Samuel L. Jackson. Drew has guest starred on numerous television series including House, Leverage, Psych, ER, The Office, CSI, Cold Case, Without a Trace, Monk, Grey’s Anatomy, and Southland.
Playing the role of Bear, Drew starred alongside Paul Reubens in the 2010 stage revival of Pee Wee’s Playhouse at the Nokia Theater in Los Angeles.