Actor Andrew Caldwell entered films and television as a young man and specialized in portrayals of geeky, overweight, socially awkward types. Caldwell made a series of guest appearances on small screen programs including The Bernie Mac Show, My Name Is Earl, and Hannah Montana before moving into films and specializing in glossy formulaic Hollywood outings. These included the big-budget action yarn Transformers (2007), the teen-oriented comedies College (2008) and My Best Friend's Girl (2008), and the Owen Wilson vehicle Drillbit Taylor (2008).