Ostrander studied theology with the intent of becoming a Catholic priest, but now describes himself as an agnostic.
Originally an actor in the Organic Theater Company in Chicago, Ostrander moved into writing comics in 1983. His first published works were stories about the character "Sargon, Mistress of War", and appeared in the First Comics series Warp!, based on a series of plays by that same Chicago theatre company. He and Timothy Truman co-created the character Grimjack, who originally appeared in a backup story in the First Comics title, Starslayer, before receiving his own title. Just prior to entering the comics industry, Ostrander had a supporting character named for him in The Daring New Adventures of Supergirl series. His friend, writer Paul Kupperberg, incorporated him into the Supergirl storyline in 1982.
Ostrander made his DC Comics debut by plotting the miniseries Legends, which was scripted by Len Wein and penciled by John Byrne. A new version of the Suicide Squad was introduced in Legends, including the team's leader, Amanda Waller. The character has been substantially adapted into animated and live-action media and is portrayed by Viola Davis in the 2016 film Suicide Squad and the 2021 The Suicide Squad. Following Legends, Ostrander and artist Luke McDonnell launched the Suicide Squad into their own title in 1987 and developed several characters for the series. Later that same year, he and actor/writer Del Close created the Wasteland series with a rotating roster of artists. He and Close had previously worked together on Munden's Bar backup stories in Grimjack.

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