Jay Leno meets Spider-Man (2002)
Superheroes and late night TV hosts have a curious history of teaming up to fight evil. The Avengers guest-starred on Letterman, and the cast of Saturday Night Live joined Spider-Man in defeating the Silver Samurai.
These unlikely team-ups combined two great tastes that don't seem to go together, but, like Nutella and Jagermeister, somehow make perfect sense when you're absolutely shitfaced.
In July 2002, Marvel Comics debuted Jay Leno & Spider-Man: One Night Only. Marvel presumably created this three-part crossover to capitalize on the release of the Spider-Man feature film, but why they chose Leno to be the star is anyone's guess. You wouldn't think Leno's audience of senior citizens would overlap much with audience for Spider-Man on the Venn diagram.
Where it goes wrong ...
We have to start with One Night Only's criminally ridiculous plot, wherein Spider-Man and Leno team up to film a General Motors commercial, then get attacked by ninjas. What the hell help is Jay Leno going to be in a ninja fight? Couldn't they, say, have them attacked by a race of aliens whose only vulnerability is really stale monologues and awkward, polite laughter?
No, instead we get a 52-year-old Jay Leno practicing kung fu on a ninja-defeating level:
Don't bother trying to find this comic in stores. Marvel divided it into three parts and tucked it non-sequentially at end of random serieses during summer 2002. This is bad for the 2.5 of you who actually wanted to read this turd, but good for the rest of us who avoided accidentally running across it.
And to make things worse ...
The writers tantalized us with a promising homoerotic subtext, yet for some reason chose not to pursue it.
Ayatollah Khomeini of Iran meets The Joker (1988)
The team-up of The Joker and Ayatollah Khomeini in Batman #429 may seem unorthodox, but there was historical precedent for it. Political leaders have appeared alongside superheroes ever since the inception of the modern comic serial. For example, Captain America and Superman took on Hitler and his Nazis during World War II. More recently, First Lady Hillary Clinton appeared with supervillain Lex Luthor at Superman's 1993 funeral.
How that hasn't been turned into an Obama campaign ad is beyond us.
Where it goes wrong ...
This cameo provides what has to be the most fucked up portrayal of '80s-era international affairs since Rocky IV.
The Ayatollah appeared in the infamous "Death in The Family" issue, in which the Joker blew up a warehouse on Jason Todd, the second Robin. On September 15, 1988, Batman fans had a mere 36 hours to call DC's 900 number and choose whether his taut little green-Speedoed ass survived the blast. Being the charitable souls they are, comic fans voted 5343 to 5271 to ice the Boy Wonder, thus sparing him a lifetime of counseling and sexual maladjustment.