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Crowning Moment of Funny: In Heir to the Empire, Leia goes to Kashyyyk and is greeted by a Wookiee who has a speech impediment that allows him to speak like a human...but she doesn't know about the speech impediment when he first opens his mouth and begins to speak perfect English. Since she's only ever met one Wookiee before this, there's a brief moment when she wonders if Chewie was just mentally challenged all this time.
Ensemble Darkhorse: The books produced at least three extremely popular characters - Thrawn, Mara and Talon Karrde, but the most surprising success story might be the relatively minor character of Pellaeon who would go on to much greater things.
Funny Aneurysm Moment: In The Last Command Han and Leia start trusting Mara after she risks her life to save their newborn children Jacen and Jaina from being kidnapped. Years later, Jacen would pull a Face Heel Turn and kill Mara. Oddly enough the irony of this was never pointed out in the latter book.
Hilarious in Hindsight: Luuke being an insane clone of Luke Skywalker becomes especially ironic when one remembers that Luke Skywalker's film actor, Mark Hamill, ends up voicing The Joker, who is an incredible insane supervillain.
Hype Backlash: After all the praise that gets heaped onto the trilogy, new readers invariably don't find it lives up to the hype.
Zahn used the Star Wars role-playing game as a mine of source material, apparently on the advice of Lucasfilm.
In the sidebar notes of the 20th Anniversary Edition, Zahn mentions a few cases where fans accused him of referencing stuff current culture, not realizing that the references were older.
Some complained of him ripping off Star Trek when mentioning the 'borg implant' that Lando's assistant had, but 'borg' is just a abbreviation of cyborg, a term that had been around for many years before.
A reference to a Correllian Corvette had some claiming he named it for the car, not realizing the car had been named for a type of small Age Of Sail warship. The fact that the name for the ship predated Zahn's writing also was a factor.
Seinfeld Is Unfunny: The idea of the Galactic Civil War having a Black and Gray Morality is now so accepted that trying to frame the Empire as purely evil is met with complaints. But back when this trilogy came out, it was revolutionary.
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