Kurt Busiek's Astro City, Vol. 2 #16 (1999)

The Tarnished Angel
Someone is murdering old, low-level supervillains in Astro City, and that community has asked one of their own, the recently paroled Steeljack, to investigate the murders. Discouraged at the inequities in life, and frustrated at how to continue, when almost everyone he could associate with is a violation of his parole, he's taken to see El Hombre, a hero with a shadowed past.
Release Date: 1999