I am an incredible geek, and since I had some time on my hands, decided to ramble about the various things I feel are highlights in Kyle's canon. Cut to save friends pages and to keep from annoying those not interested.
Dark Forces: Pretty much the original Star Wars first-person shooter, Dark Forces establishes a long tradition of Kyle Katarn visiting various typical Star Wars settings, taking out tons of Star Wars baddies, and generally being over-the-top. Originally they'd planned on not really giving Kyle a defined character, so in this game he's still pretty Generic Tough Guy, but at the same time I think the developers had the most fun with this one. Here's some highlights:
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http://www.youtube.com/watch?v=Kq1YqY4DMZUMon Mothma: The Imperials have a new weapon that's going to take us out.
Kyle: ...Crap, I joined the LOSING side?!
-The Imperials use graffiti in their prison base to express their opinions of the cuddly little Ewoks.
-If you keep an eye out in one level, the Imperials have a shipment of 50 tons of rubber duckies.
-In that same level, Kyle guns down stormtroopers while they're lined up at a urinal.
-Punchin' out Kell Dragons.
-There is an ENTIRE LEVEL of Kyle swimming in a river of sewage trying not to get tentacle raped.
-If you know where to look (IE use cheat codes) there's ewoks hidden around several levels.
Dark Forces 2 - Jedi Knight: The second game follows up on something a lot of people felt were missing from the Star Wars experience in the first installment--LIGHTSABERS. This game is the story of Kyle becoming a Jedi Knight so that he can keep a blind man from finding a particular valley. But the blind man is evil, so that makes Kyle a hero! Also, revenge for his father and saving his Korean supermodel partner who still won't become his girlfriend for several years.
Dark Forces 2 combines a cheesy plot with INCREDIBLY cheesy nineties game FMVs--meaning that it's pretty hilarious to watch.
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http://www.youtube.com/watch?v=oHDcgY2MRbI If you've ever wondered what it's like to be surprise raped by a flying torso, you can just watch this.
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http://www.youtube.com/watch?v=dH9eCZV_Vc0 None of us are kidding when we say that Kyle is a horrible pilot.
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http://www.youtube.com/watch?v=zrF1F6NoUt8 While Kyle's going "LOL I'M SNEAKING" the game's bosses just kind of...continue to be weird.
-The power of the Valley of the Jedi can make Kyle temporarily invincible. Canon provides your godmode for you!
Mysteries of the Sith: ...I don't have much to say here. Kyle defeats evil Imperial asteroids! Then he goes to the dark side and you play as Mara Jade to save him.
Jedi Outcast: My personal favorite installment of the series, the graphics aren't beautiful but they're much better than previous games--and the lightsaber system is pretty fun. When the Imperials start to mass-produce dark jedi with lightsaber-resistant armor Kyle takes his lightsaber up again to show them that "lightsaber-resistant" is NOT the same as "lightsaber-proof."
-Infiltrating enemy base by BLOWING UP THE FRONT DOOR
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http://www.youtube.com/watch?v=vL1ljx4t1ps Kyle meets Desann for the first time--and the name-calling starts right up.
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http://www.youtube.com/watch?v=Lk8jI54qAko Never trust a bartender with bad grammar. For the record, "ruby bliels" IS THE PASSWORD.
-lol they only PRETENDED to kill Kyle's partner so that he'd lead them to the Valley of the Jedi.
-You know how Kyle's username is "roundhouselaser?" Well. Kyle has a killer roundhouse lightsaber move in this game.
-More canon godmode for the final boss battle. Oh Kyle. Also you can defeat Desann by dropping parts of the level on him.
Jedi Academy: This game shakes up the series in that Kyle becomes an NPC and you play as one of his two apprentices. In this game, a familiar mid-boss comes back to suck the dark force power out of Important Places. They try to take the lightsaber system further, allowing you to customize your style, but really the only thing I enjoyed about this game is the antics between Kyle's idiot apprentices.
"Imperials! Quick, go check it out."
"Why me?!"
"Because YOU'RE the one with the lightsaber."
"... >:("
Also Kyle is a terrible teacher. First lesson and he's telling his kids that it's okay to use the dark side as long as they have a good reason.
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Interesting Characters, by which I mean APP THEM
Jan Ors
This is Jan Ors, the woman who got Kyle to work for the rebels in the first place. They've known each other for years and years, and it took them over a decade to get around to dating. This is perhaps a surprise because Jan's actor is
literally a model. Jan is essentially Kyle's Otacon; while Kyle provides the muscle of the duo, Jan provides the brains. It's her job to fly the ship, and she's the one who breaks all the computer codes, etc. Hilariously, in the original game, Jan is the character with the most voice because she gives the mission briefings and she narrates the game's manual. She can't measure up to Otacon's sheer levels of dorkery, but what she lacks there she makes up for in being able to actually handle weaponry--even though three out of four games in the series, Kyle has to save her from the bad guys anyway. But she gets to save his butt sometimes, too, so they're pretty much even.
Also, Kyle is the clingy one in their relationship. It is amusing and leads to Kyle nagging her to marry him in the comic. APP JAN, and Kyle may just audience marry her. Also her username would be awesome. Just think of all the things you could do with that last name.
Rosh Penin
Kyle has three apprentices throughout the series: Mara Jade, Jaden Kor, and Rosh Penin. The sexy apprentice, the stupid apprentice, and the stupidest apprentice, in that order. Rosh has his head in the clouds and is just a huge jedi fanboy--and he's no use in combat. He goes to the dark side for a while because he's scared. He also does things like set lightsaber-weilding robots on his friend because he wants to get to the finish line first. He's a show-off, he's competitive, and he invades Kyle's personal space. There are such antics to be had.