Chris started playing drums at the age of 13, and at age 16 decided he wanted to pursue music seriously. He spent two years at Berklee College of Music and received a degree in Music Synthesis, focusing on electronic music composition and manipulation.

As far as drummers, Pennie has cited Lars Ulrich and Stewart Copeland as his main early influences. In regard to his current playing, Sean Reinert is one of his biggest inspirations. He's also emphasized on several occasions that listening to and playing a diverse assortment of music has been an integral part in developing his style, noting such eclectic influences as 70's jazz-rock fusion group Mahavishnu Orchestra, technical metal bands Meshuggah, Cynic, and electronic-influenced groups such as Nine Inch Nails and DJ Shadow.

As stated before, Pennie is best known for his work with the Dillinger Escape Plan, but he also spent time with the pop-punk group Boxer. Formed in 1995 with another Berklee graduate, Jeremy McDowell, they became first band to be signed to the now famous Vagrant Records. They released one album, "The Hurt Process" in 1998, and broke up in late 1999. Pennie also recorded drums for his former tourmates in experimental metalcore group All Else Failed on their 2004 album "This Never Happened". Pennie describes his band, The Dillinger Escape Plan, as being 'mathcore' where they start each song with no structure and an open pallette.

As for his role in the Dillinger Escape Plan, he and guitarist Ben Weinman, along with now departed singer and bassist Dimitri Minakakis and Adam Doll respectively, formed the band in March of 1997. He and Ben Weinman write the majority of Dillinger's material and Pennie has called Weinman his "musical soulmate."

His style is best described as the juxtaposition of rapid machine-like sequences of rudiments and jazz-inflected expressiveness. Pennie also takes care of a lot of the electronic influence in the band’s material in the studio as well as onstage, triggering effects and loops with footswitch pedals.

Currently, he is working in the studio with rock band Coheed and Cambria, due to the fact that regular drummer Josh Eppard has left the band. He is stated to appear on the new album (Good Apollo I'm Burning Star IV; Volume II: No World for Tomorrow) for a majority of the tracks.

On June 28th, 2007, Coheed and Cambria announced on their Myspace that Chris Pennie is officially the new drummer for the band.

In 2010 Chris Pennie made a great performance at the Modern Drummer Festival.

On 2nd November 2011, Coheed and Cambria announced on their Facebook page that Pennie had left the band. Chris also announced: he had parted ways with Coheed and Cambria, in order to focus on other projects such as Return to Earth and Fight Mannequins.