Weissman began his career in the mid-1990s in alternative comics with the self-published series Yikes! (later published by Alternative Comics), which featured Charlie Brown–like characters modeled on classic Hollywood monsters.
Around the end of Barack Obama's first presidential term, Weissman transitioned into political cartooning after being recruited by Fantagraphics to produce a weekly online strip focusing on Obama and his cast of characters (Secretary of State Hillary Clinton, Vice President Joe Biden, and the Obama family) experiencing life in a parallel universe. This was collected in graphic novel form in Barack Hussein Obama (Fantagraphics, 2012). During this period, Weissman's political cartoons also appeared on the humor website Super Deluxe.
In addition to this solo titles, Weissman has contributed to such anthologies as Buzzard, Small Press Expo: SPX '98, Bizarro Comics, and Kramers Ergot issues #9-10. In 2024, Weissman and Sammy Harkham co-edited the anthology Peep, co-published by Brain Dead and Kyle Ng.
Awards
1997 (nomination) Ignatz Award for Breakout Talent
↑Weissman, Steven (1998). "The Fashion Victims (a Yikes! story)". In Oarr, Chris (ed.). Small Press Expo: SPX '98. Small Press Expo.
↑Plowright, Frank. "Bizarro Comics". The Slings & Arrows Graphic Novel Guide. Retrieved April 21, 2026. Most stories charm to some degree, but appreciation of many will depend strongly on your response to the work of marmite creators such as James Kochalka and Steven Weissman.
↑McCulloch, Joe (August 2, 2016). "KRAMERS ERGOT 9". The Comics Journal.
↑"Kramers Ergot 10". Politics and Prose Bookstore. Retrieved April 21, 2026. Also included: Rick Altergott, Marc Bell, Blutch, ... and Steve Weissman....
↑Brian, Nicholson. "Peep". The Comics Journal. Retrieved April 21, 2026.