In 2002, after taking a break from his main priority, Skiba recorded a split acoustic EP with Kevin Seconds (of 7 Seconds fame). The EP, titled Split, was released on Asian Man Records. He has also contributed to albums released by Hubcap and the Atari Star. In 2005, still between commitments with the Trio and after relocating to Los Angeles, Skiba hooked up with Josiah Steinbrick of F-Minus to begin work on another side project, Heavens, in which he sang and Steinbrick wrote the music. Their album, Patent Pending, appeared in fall 2006 on Epitaph. By 2009, Skiba was once again back with Alkaline Trio for the group's sixth studio album, Agony & Irony. The following year, Alkaline Trio returned with This Addiction, the group's first album released on its own Heart & Skull imprint.

On the heels of This Addiction, Skiba released his debut solo album, Demos, which featured demo recordings made on his home computer. Two years later, he delivered the full-length Babylon, which showcased his backing band the Sekrets, featuring AFI bassist Hunter Burgan and My Chemical Romance touring drummer Jarrod Alexander. He then returned to Alkaline Trio for 2013's My Shame Is True. In 2015, Matt Skiba & the Sekrets released their second studio effort, KUTS, featuring the single "Krazy." ~ Jason MacNeil