Comics books, as all mediums of art, deal with the human condition. At the heart of drama is conflict, and sometimes dealing with big touchy subjects is how the genre or medium can grow. Other times, however, a misguided attempt can end up setting the whole industry back.

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From manic changes in mood to not very well thought out attempts at breaking new ground, the medium has had its fair share of mistakes. The road to cringe is paved with good intentions, and while these comics might not be the all-time worst books to ever see print, they may very well be the hardest to actually read.

CW: Racism, Black-Face, Sexual Assault, Homophobia, and Islamaphobia.

10 Action Comics #593 Dared To Make A Porno With Superman

Action Comics #593 Superman Big Barda Mister Miracle

While his runs on Superman and X-Men are fondly remembered, John Byrne's record isn't spotless. In what is arguably the most controversial story in the iconic writer's portfolio, the Man of Steel is brainwashed into filming an adult film with Big Barda. Due to the machinations of Sleez, a low-ranking minion of Darkseid, both heroes have their inhibitions and libidos manipulated. It's only thanks to the last-minute arrival of Big Barda's husband, Mister Miracle that she and Kal-El don't make one helluva mistake.

9 X-Men: Holy War Didn't Know How Catholicism Worked

X-Men Nightcrawler Holy War 3

Kurt Wagner's faith has always been a major element of his adventures as Nightcrawler, so it made perfect sense for incoming X-Men writer Chuck Austen to use it as the central hitch of his new story. Unfortunately, Austen never seemed to actually do any research about Catholocism and instead of making a hard-hitting tale about faith in the face of adversity and bigotry, he created one of comics' most infamously stupid world-conquering schemes.

Planning to make the satanic-looking Nightcrawler the new pope, the Church of Humanity then wanted to fake the Rapture and thereby make the world blame mutants. That, combined with sexist undertones and a seeming confusion on how crucifixion actually works, cemented this book's place in the hall of yikes.

8 The Rise of Arsenal Didn't Know How Drugs Worked

Roy Harper

One of the darkest moments for the Green Arrow cast was in Green Lantern #85 by Dennis O'Neil, Neal Adams, and Dick Giordano when it was revealed that Roy Harper, A.K.A. Speedy, had been using heroin behind his mentor's back. Flash forward to the '00s and Roy had not only moved past his addiction but also fathered the adorable Lian.

Things took a turn for the worst however when Lian was killed off as a shock death in the critically panned Justice League: Cry for Justice. This spun out into The Rise of Arsenal by in which writer J.T. Krul takes Roy back to the bottom in a tale that tries to tackle drug abuse and addiction with, much like the previous entry, not actually seeming to know how either works.

7 Marvel MAX's Rawhide Kid Insulted Gay Men

Rawhide Kid Marvel Max

There's a relatively old saying in the LGBTQ+ community (a saying which likely also has ties in other minority groups) that goes "I'd rather you just call me a slur." This tends to be reserved for when an attempt by a company to appeal or represent the community is so misguided and offensive that they may as well have just put out a statement referring to members as a derogatory term than put the time and effort into doing what they did.

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Marvel's Rawhide Kid series by Ron Zimmerman is exactly that. Touted at the time as a landmark gay character, the Kid was depicted as every outdated gay stereotype of the last few decades.

6 Holy Terror Ended Up Being Exactly What It Tried To Be

Holy-Terror

Frank Miller has always had some pretty noticeable flaws when it came to writing women and people of color. 300 reads as if ancient Greeks had the propaganda tools of World War II America. Holy Terror, on the other hand, was actually aiming to be that. Pitched to DC as a Batman book which would act as an homage to the incredibly racist anti-Asian books of the Golden and Silver AgesHoly Terror would end up being about a totally-not-Batman hero named The Fixer who fights Islamic terrorists. One could be mistaken for thinking it was made at the height of Post-9/11 hysteria because the book was actually released in 2011.

5 Punisher #60 Puts Frank Castle In Black Face

black-punisher

It's very hard to imagine what was going on in the writer's room of Punisher #60. Written by Mike Baron and Marc McLaurin with art by Val Mayerik, the story revolves around the bizarre premise of "what if Frank Castle wore Black-Face". Revealed in #59, the vengeful anti-hero had been disfigured by his archnemesis Jigsaw and asked his underground doctor to completely change his face. She did that and more as the proceeding story sees Frank learn about the black American experience by being beaten by racist cops and teaming up with Luke Cage.

4 Avengers #200 Assaulted Marvel's Wonder Woman

Marcus Avengers 200

It's really been over the last 20 years that Carol Danvers has cemented her place as Marvel's Wonder Woman. She has the power, the courage, and now with a major motion picture, she also has the marquee value. However, things weren't always looking up for Captain Marvel.

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Back during her Ms. Marvel days, she suffered a great tragedy when a slapshot 200th Avengers issue celebration ended with the character being effectively sexually assaulted by her own predestination son. It ended even worse as Carol walks off into the figurative sunset with her assaulter while the Avengers cheer her on. It is without a doubt the worst moment in mainline Marvel superhero comics.

3 Superman's Girl Friend, Lois Lane #106 Is A 70s Curiosity

Superman Black Lois Lane

In April of 1970, writer Dennis O'Neil shook DC Comics by having Green Lantern Hal Jordan brought face to face with his, and by extension the company's, history of the black community. Soon after, in November of that same year, the company would immediately fall on its face. As can be seen above, Lois Lane, much like Frank would years later, dons black-face in Superman's Girl Friend, Lois Lane #106 by Robert Kanigher and Werner Roth. The ghoulish concept of her pretending to be black aside, the worst part is easily the overtly preachy "why can't we all just get along" narrative that the book makes Lois the mouthpiece of. This hits a climax when Lois asks Superman, a literal space alien, if he would still love her even if she was black.

2 The New Guardians Had No Excuse Being So Bad

extrano header

The New Guardians ongoing series from DC isn't on here because it features anything as immediately awful as black-face or approved sexual assault. It's on here because of how relatively recent it is compared to others (1988) on this list and because of just how many times it fumbles at its own premise. Created as an ethnically and sexually diverse superhero team, The New Guardians ended being a collection of bad stereotypes fighting literal AIDs goblins and cocaine empowered supervillains. With characters like Extraño, who somehow beats the Rawhide Kid at "I'd rather you'd just call me a slur," it's no wonder why the series flopped.

1 Marville Might Very Well Be The Actual Worst

Marville

Most of the comics on this list were ignorant mistakes made with the best of intentions. Marville by Bill Jemas and Mark Bright, was not that. A pseudo-satire/deconstruction of superhero comics, the crude and tasteless 2002 series from the House of Ideas somehow beats Ultimatum as the single worst book the company ever published. While the failed Ultimate Comics crossover had its repulsive moments, it was all in service to the dark and dower theme of the story. Marville on the other hand reads like a bad episode of South Park with none of the comedic wit of Matt Stone and Trey Parker. It is edgy early 00s "it's funny because it's offensive" trash.

NEXT: 5 Best Marvel Comic Crossovers (And The 5 Worst)