Funny / Star Trek Expanded Universe

Novels

  • Before Dishonor as a whole, but anything to do with Pluto in general.
    Well, that solves that dilemma.
  • In The Kobayashi Maru, Kirk, Sulu, Scotty, and Chekov are trapped in a crippled shuttlecraft and decide to pass the time by telling stories of their runs through The Kobayashi Maru test. Kirk explains how he managed to "win" by hacking into the computer the night before and tweaking the code slightly...
    Kirk:"This is Captain James T. Kirk, of the USS Potemkin. We are on a rescue mission in search of a civilian freighter registered with the United Federation of Planets. We mean no harm, but we will defend ourselves if necessary."
    Klingon: Captain Kirk? The Captain Kirk?
    Kirk fought a smile as his bridge crew exclaimed in a single voice, "The Captain Kirk?" The "dead" navigator began to laugh.
  • Legends of the Ferengi is basically the Guide Book as rewritten by Honest John's Dealership. It never dips below "very funny", but the CMOF has to be the deadpan description of what happens when Time Travel for Fun and Profit meets Gambit Pileup:
    17822 was a very interesting year on Ferenginar. In that year alone, over twenty thousand Grand Nagi held office; the Ferengi Financial Exchange crashed 3152 times, while setting 12322 record highs; there were 41098 civil wars; an unknown number of Ferengi-incited interstellar wars (estimates are in the millions); and the Ferengi sun went nova at least once a week.
    In other words, 17822 was the year Ferenginar discovered time travel.
  • The TNG novel Q-in-Law, in which Q and Lwaxana Troi meet. Just the tagline should give you some idea: "Two of the most powerful forces in the galaxy are about to collide..."
    • Q learns that he made a big mistake"
      Riker: She's really beating the stuffing out of him. What should we do?
      Worf: Sell tickets.
    • The B-plot of Wesley's adventures with a Dojikko "servant" he received as a gift. If Amusing Injuries can happen in a non-cartoon setting, this qualified.

Comics

  • Pretty much every moment with Harry Mudd in the second volume of DC's Star Trek comic.

http://tvtropes.org/pmwiki/pmwiki.php/Funny/StarTrekExpandedUniverse