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You've probably all found that many video games become extremely easy after one or two play throughs. So let's make the games challenging again, shall we?

Post any challenges for any games you want to. Be sure to include some rules (if nothing else, ban cheating devices), an end point, and anything else you deem neccessary. If you decide to try anything posted, you can do it secretly, or keep a constant update in this thread.

Here's a few of my suggestions.

Speedrun
Game: Almost any
Goal: Get through the game as fast as you can.
End Point: This will vary by game, but I would typically say that you've beaten the game when you reach the credits.
Rules:
-No cheating devices
-Only use THAT game (ex. don't trade in a high-level pokemon with super-powerful moves)
-In-game glitches/tricks are generally allowed; use your judgment on these
-Replay bonuses are not allowed (ex. the Grade shop in Tales of Symphonia)
-Additional rules can be added on your own varying with the game
Tips:
-Skip as many sidequests as possible. You don't need to fill your pokedex, you don't need that super-powerful weapon, you don't need 100% completion, you just need to reach the end of the game.
-You don't need to save. Feel free to save, explore to find the best route, turn the game off and back on, and then take that route.
-Don't power-level or build up anything beyond what's necessary. That just takes longer.

100% Completion
Game: Almost any
Goal: Do EVERYTHING in the game
End Point: When you've completed everything.
Rules:
-No cheating devices
-Only use other games if essential (ex. no trading pokemon unless it evolves through trading or the pokemon can't be caught in the game)
-In-game glitches/tricks are generally allowed; use your judgment on these
-Replay bonuses are allowed
-Additional rules can be added on your own varying with the game
-You may consult walkthroughs, but minimize their use
Tips:
-It doesn't matter how long it takes, so don't worry.
-Do even small stuff that doesn't actually impact the game; it counts.
-Unless there's something that keeps a record, you do not need to beat all the different monsters or collect all of the different items.
-Multiple playthroughs may be needed to finish this, so take advantage of your knowlegde of the game's layout.

Monotype Challenge
Game: Pokemon, any version
Goal: Beat the game using only one type of pokemon
End Point:
R/B/Y/FR/LG - Capture/Defeat Mewtwo
G/S/C - Defeat Red
R/S/E - Beat the Elite Four
D/P - I haven't gotten far enough to say. It's a new enough game that I wouldn't recommend trying this yet.
Rules:
-No cheating devices. The only exception is if the type you need does not show up for a while, you can use one to capture one of the pokemon at level 5 of its basic form.
-Dual-types are allowed as long as one of those types is the one you're using (ex. Starmie could be used for either a water or a psychic team)
-No legendaries (my definition of legendary pokemon is any member of any legendary trio, any pokemon that can only be battled once (besides Sudowoodo and Snorlax), and any pokemon impossible to obtain legally (including Mew; so no Mew glitch))
-No two members of the same species or evolutionary tree
-You may capture pokemon not of that type for learning and using HM moves (HM slaves)
-If your first pokemon is not that type, then you mayb use him to capture your first pokemon of that type and nothing else
-You may not trade pokemon/items/TMs to the game unless the pokemon only evolves through trading (Machamp, Alakazam, etc.), the pokemon would appear at that point (Magikarp after getting the Old Rod), or the item is needed for evolution into the needed type (ex. Metal Coat for Scyther/Onix in a steel team).
-Pokemon not of the proper type may be used if they will evolve into that type (ex. You can use Charmander with a flying team).
Tips:
-Take advantage of pokemon learning moves not of their type through experience or TMs
-Minimize the number of HM slaves; after a while they will take up space for your team
-Power-level; otherwise your team will encounter trouble against some gym leaders
-Use various resources to see what moves your team will be able to learn and balance out the team according to that.

Feel free to post any others that you can think of.

Cave of Ordeals: I'm not far enough, but I'll give it a shot when I've reached it.

I'm actually trying an electric monotype challenge with Yellow version right now, and I've found that it's really annoying to go with one pokemon, and catch a second much later in the game. At the Rock Tunnel, my Pikachu is level 37, and I can barely raise my Magnemite.

All right.

Yellow Version is pretty much Red/Blue Version, but following the anime storyline. You start with a Pikachu who follows you around (your rival starts with Eevee, though), you battle Jessie and James instead of several nameless Rockets, your Pikachu won't evolve if offered a Thunderstone, etc. It's an interesting game since many of the alterations to it haven't been reused, but some people don't like it since it targets fans of the anime and not the games.

The training's been getting better (Magnemite learned Sonicboom, so he's able to hold his own much easier), but yes, barely. The Rock Tunnel is full of rock pokemon and hikers, and most rock pokemon in RBY are also ground (immune to electric attacks). In order to raise Magnemite, I was sending him out and then switching to Pikachu, which means they got a turn to attack Pikachu. It also took a few Slams or Seismic Tosses to knock out these pokemon, so Pikachu was taking a lot of damage.

But I got to have Pikachu Seismic Toss and Onix, so it's all good. :]

Origonal
Game: Tales of Symphonia

Goal: Finish the first disk without changing weapons, keeping the first weapons you get.
End Point: Defeating the game/first disk

Rules:
-No cheating devices.
-No changing weapons
-Must have a very new file, not replaying the game after beating it and getting the EX gems or extra gold, etc.
-You may use the Devil's Arms when you get them, but after fighting Abyess you may not.

Tips:
-Get A LOT of items, and use Sheena to power up your weapon with an element.( helps alot )
-Mainly use Lloyd, Raine, Kratos/Zelos in your team. The last member can be any. This is the team I used to defeat the game.
-Save up your hourglasses for desprate times.

Comment from me: " This is so hard! Trust me....it Takes A loooonnnggg time! So many deaths....* sighs *"

I know a video game challenge, that creates the ultimate close to real life experience:

In any game you play, if you lose and it's game over, start the whole game over. For example: in New Super Mario Bros Wii, a enemy kills you and you lose a life; now you start the whole game over again.