Gary Cole, Actor: Pineapple Express. Gary Cole was born on September 20, 1956 in Park Ridge, Illinois, USA as Gary Michael Cole. He is known for his work on Pineapple Express (2008), Office Space (1999) and Talladega Nights: The Ballad of Ricky Bobby (2006). He has been married to Teddi Siddall since March 8, 1992. They have one child.