Cassaday started his comicbook career doing some work for various small publishers like Boneyard Press and Caliber Comics. A few convention trips to San Diego and New York led to a series of Ghost (1996-1997) covers and a pencilling job on Ghost #27 for Dark Horse and the 1997's Teen Titans Annual #1 for DC.

His first high profile work was the 1997's Ka-Zar: Sibling Rivalry #-1 for Marvel. Writer Mark Waid who helped him secure this assignment, also showed samples of Cassaday's pencils to Homage, which resulted in doing the Desperadoes (1997-1998) mini-series.

After that, Cassaday pencilled and co-wrote the two-issue X-Men/Alpha Flight (1998) mini-series and the three-issue Union Jack (1998-1999) mini-series with writer Ben Raab for Marvel.

At the moment Cassaday is the artist on the highly acclaimed Planetary (1998-now) series with writer Warren Ellis for DC/Wildstorm.

In 2002, John Cassaday, together with writer John Ney Rieber, were responsible for the relaunch of the Captain America series, under the Marvel Knights imprint.

In 2004, Cassaday's popularity exploded when he, together with Buffy: The Vampire Slayer creator Joss Whedon, collaborated on the new Astonishing X-Men series for Marvel.

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