Even though Iron Man debuted in the 1960s, it was in the following decade that his character got humanized further. Tony Stark has always been a womanizing tech genius who moonlights as a superhero, but the comics of the 1970s saw him struggle with real-world issues like alcoholism that made him more relatable.

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In addition to his personal struggles, he also faced longtime allies turning against him. Some of these combatants included Angel and Captain America, who would later fight Tony in both comic book and film versions of the Civil War narrative. Aside from such storylines, the character also received a meta-narrative with him attending a Comic-Con and meeting actual comic artists and writers. The 1970s posed daunting challenges for the Avenger, which fortunately resulted in some of the best Iron Man comic book issues ever.

"Demon In A Bottle" (Iron Man Vol. 1 #120-128)

Tony Stark sweats and looks at his reflection in the mirror in Iron Man comics.

Despite his immense power and skills, even Tony Stark can have his share of bad days. When he and Namor fail to save an island and when he finds his armor malfunctioning, he resorts to binge drinking. This not only ruins his relationship with his loved ones but also makes him question his own heroism.

Demon In A Bottle is filled with realistic moments such as Stark taking out his drunken anger on his butler Jarvis and his love interest Bethany Cabe talking about an old flame's addiction-induced death. The storyline is still iconic given how Stark's struggle with alcohol has defined the character even in scenes from Iron Man's MCU films.

"Beware...The Blood Brothers!" (Iron Man Vol. 1 #55)

Cover for Beware the Blood Brothers along with a comic panel featuring Thanos talking to Iron Man

Iron Man aids the planet of Titan in this interstellar adventure that finds him joining forces with Drax the Destroyer to fight Thanos. The cosmic warlord aims to seek control over Titan with the help of the twin ape-like aliens known as Blood Brothers. With a third-act twist, the plot is left open-ended with Iron Man vowing to challenge Thanos yet again.

The comic is a perfect example to showcase Tony Stark's benevolence. Even though he builds weapons and has his own share of rivalries, he is still willing to help innocent civilians be it on planet Earth or a world as distant as Titan. Drax does extend his gratitude towards the end and strikes up a friendship. Also of interest is the issue's main antagonist: Thanos, who is arguably the MCU's best villain and who would kill Iron Man in Avengers: Endgame.

Giant-Size Iron Man (One-Shot)

Iron Man being struck by Angel in mid-air in Marvel Comics.

Giant-Size Iron Man is a three-in-one comic special with each story featuring a notable Marvel superhero. The first chapter opens up with a corrupted Angel who engages in intense aerial combat with Iron Man. In the second one, the hero ends up getting tailed by Hawkeye who is introduced as an egoistic marksman. The final story includes the shapeshifter Chameleon posing as Captain America and creating a clash between the two Avengers.

It is a recurring trope for superhero comics to have allies fight against each other. So, it's only exciting to find Iron Man going against an X-Man, a S.H.I.E.L.D. operative, and the leader of the Avengers. Captain America and Iron Man would of course go on to fight each other in the years to come with essential Marvel comics such as Civil War.

"At the Mercy of My Foes/Friends!" (Iron Man Vol. 1 #118)

Tony Stark falling off a plane on a comic book cover

As Iron Man is invited to a S.H.I.E.L.D./NATO conference, he and Nick Fury end up facing some rogue agents. Stark seeks to unravel the conspiracy but ends getting knocked out and thrown out of a plane. The big reveal in the comic is his new suit which is enclosed within a briefcase cuffed to his wrist. In mid-air, Stark manages to dramatically suit up just a few minutes before hitting the ground.

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This particular scene (that was also featured on the cover) showed the limitless possibilities of Stark's technology. Instead of bulky armor, he could now resort to portable versions. An aerial suit-up scene also found its way in Iron Man 3 but loyal comic book readers knew it first occurred in this issue.

"Anguish Once Removed" (Iron Man Vol. 1 #116)

_Iron Man lifting one of Madame Masque's machines

Because of his business commitments with Stark International and his status as Iron Man, Tony Stark is no stranger to assassination threats. The Spymaster orchestrates a similar plan with SHIELD agents and Ani-Men. As a bomb sets off in his penthouse, Tony Stark must fight to survive.

The presence of Ani-Men as Iron Man's main comic book villains is interesting as for modern readers, they would seem like laughable foes. The anthropomorphic characters are still a classic remnant of the over-the-top 1970s-era storylines. This angle itself makes Anguish Once Removed a time capsule of sorts and indicative of the foe the Golden Avenger typically battled in his series.

"Convention of Fear" (Iron Man Vol. 1 #72)

Tony Stark reading the newspaper

Even heroes deserve breaks every once in a while. So, in a very meta move, the writers of Iron Man had the Avenger attend a San Diego Comic-Con. But his visit is cut short when villains like Man-Bull and Whiplash show up. The conflict with the villains is straightforward but it is his experiences at the comic convention that is noteworthy.

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Not only does he meet Iron Man writers and artists such as Roy Thomas but he also encounters a group of enraged Star Trek fans who ask him to sign a petition to get their favorite show back on the air. Stark also attempts to purchase an Iron Man comic but he is unable to as he's out of cash. And if it was not enough, Stark even offers an Avengers credit card which yet again gets rejected! It's such hilarious moments that make Convention of Fear worth reading.

"There Lives A Green Goliath!" (Iron Man Vol. 1 #76)

Iron Man Fighting and Knocking Out The Hulk in Marvel Comics

What's worse than fighting Hulk? A robotic version of Hulk! When Mandarin creates an android Hulk, Iron Man must give it all to not just save himself but even his business rival's daughter Janice Cord. The comic is actually the same as a 1960s Iron Man comic issue. The reprint happened with the same story being readjusted in the continuity as the 1970s comics.

The issue has enough adrenaline-fueled action to engage readers. Even though Hulk and Iron Man have clashed in numerous comics, this fight with an alternate version of Hulk is also a noteworthy event in the characters' long-lasting rivalry. Their conflict would later be portrayed in the MCU in Avengers: Age of Ultron, where Tony would wear the Hulkbuster armor to battle the Green Goliath and almost decimate an empty city.

NEXT: 10 Best Hulk Comic Issues of the 1970s