Spider-Man is the most important comic book superhero of the past 50 years – and the main reason is because he’s always been daring. Even when he was introduced in 1962, by writer-editor Stan Lee and artist Steve Ditko, he was a brave concept: a superhero motivated not by altruism (like Superman and most others), or even by revenge (like Batman), but by guilt. (While he selfishly uses his powers for a showbiz career, he fails to stop a burglar. As a result, the burglar goes on to kill his uncle.) In 1971, Spider-Man tackled drugs, in a story that fell foul of the censors – and though that one belongs here, it’s already covered in a previous article, 5 Memorable Moments in Comic Book Censorship.

He is still daring today – and not just in comics, as we can see from Spider-Man: Turn Off the Dark, one of the most ambitious musicals in Broadway history. But here are the boldest moments of the past 50 years. Some have been successes; others have backfired terribly. That’s what boldness is all about…

1. The Night Gwen Died (1973)

As teenager Peter Parker, Spider-Man’s high-school sweetheart was the lovely Gwen Stacy, a popular supporting character. By 1973, it was becoming a little too cozy, so artist John Romita suggested that they kill her. In one comic, the Green Goblin (aware that Parker was Spider-Man) kidnapped Gwen and threw her from the top of the Brooklyn Bridge.

As anyone who saw the movie Spider-Man (2002) would recall, this is exactly what he did to Mary Jane Watson, but Spider-Man saved her. In the comics, Gwen was not so lucky. Spidey swept down to catch her, only to discover that she was dead. In case this wasn’t shocking enough, writer Gerry Conway included a snapping sound effect when he caught her, implying that her death was caused by the shock of being caught while falling at a great speed (meaning that it was Spider-Man’s fault). Whatever the case, it was truly shocking for a children’s comic (as it was in those days). But despite many complaints from readers, she never returned to life, unlike many comic book characters.

Did it work? It wasn’t exactly a feelgood comic, but The Night Gwen Stacy Died is now considered a classic story. It also showed one of the most startling things about Spidey: sometimes the good guys lose.

2. Spider-Man in Black and White (1984)

When a superhero is famous, not just with comic book readers but also with the public, you don’t go changing his costume. However, in 1984, Marvel Comics gave Spider-Man a new, black-and-white one. It was a controversial decision, leading to the theory that it was introduced so the artists wouldn’t need to draw so many webs. To make it even more useful, the costume was an alien lifeform, which Spidey could transform at will into regular clothing. Though he wore the costume for some time, it eventually went evil, and they parted ways. With a new “host”, it later became the monstrous super-villain Venom.

Did it work? The black costume eventually grew on readers – until it was removed, as the familiar red-and-blue jumpsuit had been licensed to too many merchandisers. Spider-Man still occasionally wears a black suit – a duplicate of the alien one – most recently when he was in a particularly dark mood.

3. The Clone Saga (1994-95)

To combat falling sales, Spider-Man’s writers and editors agreed that he had become too happy, married to his sweetheart Mary Jane Watson. The solution – worthy of any soap opera writing team – was to hearken back to a 1975 story, in which the hero had been cloned, and the clone had supposedly died. The clone returned in The Clone Saga, an epic story that lasted two years. In the end, it was revealed that, for 20 years (of our time), Spider-Man had been a clone. The real Spider-Man had been hiding for all those years, thinking that he was the clone. (Got that?) Now that this was revealed, the real clone was allowed to lose his powers and retire gracefully to his life of marital bliss, while the original Spider-Man took over again, with all his life issues intact.

Did it work? Not at all. An email group, The Spider-Man Expatriates, promoted a boycott of any comics that suggested their hero was an impostor. They weren't simply a vocal minority; subscriptions fell to 235,000—a 30-year low and a 60 percent drop from 1993. Eventually, Marvel did a desperate about-face, restoring the clone's powers and revealing that, whatever they said, he wasn't really a clone after all. (Still got that?) “Somewhere, the 'Clone Saga' became the catchphrase for all that is wrong in everything, not only comics,” said Howard Mackie, the only Spider-Man writer who didn't lose his job in the process. “World War III will be caused by the ‘Clone Saga.’”

4. Sins Past (2004)

In one of the more alarming stories, Spider-Man met a woman who looked exactly like his tragic sweetheart, Gwen Stacy. He later discovered the truth: she was one of a pair of twin siblings who had been secretly born to Gwen after an affair with… Norman Osborn—the Green Goblin! Using his scientific genius, he had now aged them prematurely, in an attempt to defeat Spider-Man. The idea that sweet Gwen would have an affair with Osborn was not taken well by some fans…

Did it work? The story, besmirching Gwen’s memory, was so badly received by fans that its writer, J. Michael Straczynski (better known as the creator of the TV series Babylon 5), later asked his editors if he could “retcon” the story so that it never happened. As far as future writers (and most fans) are concerned, it never did.

5. Unmasked! (2006)

In the mini-series Civil War, Spider-Man revealed his secret identity to a large media throng. As the press corps went wild, his friend Tony Stark (alias Iron Man) congratulated him: “Soak it up, Peter. You’re bigger than Elvis now.” It was promoted as “the most shocking event in comic book history,” and sure enough, fans reacted strongly. However, they had to get used to it. “There is no going back after Civil War,” said Marvel editor-in-chief Joe Quesada at a comic-book convention. “We use these events to modernize our characters.”

Did it work? It was perhaps the most talked-about story of the year—and some people were angry. In one blog, US comic-book retailer Ryan Higgins called it “the biggest mistake in the history of modern comic books.” Within days, the internet chat rooms were filled with stunned comments like “Spidey sold out!” But whatever Quesada had said, it wasn’t intended to last. Instead, everything was back to normal after a year, in an even more controversial story…

6. Brand New Day (2007-08)

Spider-Man’s happy marriage was still bothering the folks at Marvel, leading to perhaps the most daring move in Spider-Man history. To save the life of his Aunt May, who was dying in hospital, Spider-Man made a deal with Mephisto, lord of the underworld, to save her. The price: his marriage to Mary Jane would not only be over, but it would never have happened, and their memories would also be wiped.

Did it work? Like the Clone Saga, it angered many fans, again not happy with history being changed. However, while many boycotted Spider-Man comics, the sales were as strong as ever, with a revitalized (and newly single) Spider-Man.

7. Spider-Man is… Andrew Garfield? (2010)

Sure, it might not seem as daring as many of the other things on this list, but Hollywood casting can often be a gamble – especially as superhero fans can be violently opposed to casting decisions they don’t like. When a certain actor is strongly connected with a role, it can be even worse. So in the next Spider-Man movie, the very popular Tobey Maguire will be replaced by… some English guy nobody’s heard of? When this was revealed, the chatrooms were abuzz – and many people weren’t happy.

Did it work? It’s too early to tell, but since Andrew Garfield has a major role in The Social Network, the gamble might have paid off. In that film, he played a badly-treated geek – perfect training for Peter Parker! (Oh, and he proved that he can do an American accent.)

8. Turn Off the Dark (2010-11)

Even before the onstage accidents and delays, Spider-Man: Turn Off the Dark seemed like a dangerous idea. The most expensive (costing twice as much as the previous record-holder) and logistically challenging show ever staged on Broadway? A score by Bono and The Edge? (Great rock musicians, sure, but they’d never written a musical. Nor did they make their reputation with light and breezy show-stoppers.) A book co-written by the divisive Broadway director Julie Taymor? A little-known cast forced to learn trapeze along with the singing and dancing? Broadway shows are always a gamble, but never more than this one.

Did it work? Not so far. Opening night was delayed due to safety issues, three of the cast were injured (including one of the main cast, who quit soon afterwards), and critics were unimpressed by the previews. We await opening night on March 15 (subject to change)…

Mark Juddery is an author and historian based in Australia. His latest book, Overrated: The 50 Most Overhyped Things in History (Perigree), is already causing a stir. You can order it from Amazon or Barnes and Noble. You can see a slideshow excerpt from the book, and you can argue with Mark's choices (or suggest new ones) on his blog. Mark offers one tip: If you want to say "This book is overrated"... it's been done.