Oh god.  I still remember the screams of frustration from the players.  It's just a horrible, horrible thing to put yourself through.

Also worth a read is Medieval II Total War- A Scotsman in Egypt.  It's an amazing piece of writing following the first Scottish Empire, assuming that Scotland was a power player in the crusades.  The story starts off with the capture of Jerusalem by Edmund and Edward, the two Scottish brothers who decided in one drunken night that they would sail to the holy land on the Pope's orders, and carve themselves a kingdom from the desert wastes.

A word of warning, it's deeply engrossing, and very... very... very long.  According to the archive it has 74 chapters.  Only read it when you've got some time on your hands.

Here's a video LP that held my attention, it does take a long time to watch from beginning to end however so it's better watched with a lot of spare time on your hands. They start from the bottom of the page upwards.

http://www.spoonyexperiment.com/category/phantasmagoria/

Sorry for the thread necromancy, but I've got some more for you.

7.62mm is an amazingly poorly done game.  It is filled to the brim with bugs, mistranslations, and bits of speech where it's half English, half Russian.  It is, however, a well done tactical game, with tons of weapons, weapon mods, and a remarkably rounded out tactics system.  The LPer hires goons from the SA board in the game, and documents their progress through a war-torn South American country.

In the LP of X-COM: Apocalypse, Guavamoment gives one of the hardest tactical games around his own story, setting up scenes, and again giving names of Goons to the people he hires.  It's fantastically done, and was what got me into X-COM in the first place.  If you like this one, make sure to check out UFO DEFENSE, the first game, which is equally well done, except for some forum faggotry later on.  You'll know it when you see it.

Princess Maker 2 is absolutely bizarre.  It's a game where you raise a little girl given to you by the gods, and try to make sure she marries the right person.  WATCH!  As Synthorange makes his little girl go and lumberjack all day!  SCREAM!  As he forces her to do battle with perverts, sea-monsters, dragons, and THE GODS THEMSELVES!  CALL SOCIAL SERVICES!  As he sends her off to work in a bar at age 13!

Finally, we have the Worms: Armageddon tournament, which is full of laughs and misadventures, and is refereed by Psychadelic Eye, who has a crazy French Canadian accent, which makes everything better.

Let's Play Sonic 2: Special Edition is one of the strangest LPs I have ever seen, partially because the game doesn't exist.

I personally Enjoy the LP of GOD HAND by KungFu Jesus. This could probably have something to do with my love of the game, though.

The newer Oregon Trail LP for some reason is the funniest thing I have ever read.  I completely lost it when they get to the first river and someone offers this suggestion:


It's amazing how funny regular people can be when they come together for a good purpose. 

I actually registered just to make a couple recommendations.

First, Schildkrote's Persona 3 Lets Play. Second, Jerusalem's Grand Theft Auto 3 Lets Play.

Both of these LPs are unique. They aren't necessarily all about humor, though it's there. Instead, they are sorta screenshot novelizations from the perspective of the main characters. I found both of them to be very interesting, and great reads. They are fairly long (especially the GTAIII one) but totally worth it if you're into that sort of thing.

As for more humorous LPs, I suggest any Eversion Lets Play ever. Eversion is a fun little net-game with a horrible secret roiling underneath a rotten surface. In my opinion, Diseased Crab is one of the best LPers on the net, and his LP of the game is fantastic. For extra lulziness, check out Quantum Crayon's absolutely HILARIOUS blind run.

Maxwell Adams and crew make great commentated LPs.  They have a website here.

The Oblivion LP in particular is hilarious, most of their time was spent showcasing horrible mods and generally breaking the game as much as possible.

I also recommend GTA: Vice City, mostly for the flying tank.

I also highly suggest you check out Slowbeef's Metal Gear 2 LP, just for the sheer insanity that goes on later in the game.

And also Retsuperae. Two guys decide to commentate over terrible LPs, laughing as the players fail or just making fun of their voices. Pretty funny.