Red Chocobo's Pokemon Let's Plays. Without a doubt.
Pokemon Emerald [http://lparchive.org/Pokemon-Emerald/]
Pokemon Crystal [http://lparchive.org/Pokemon-Crystal/]
Pokemon Quartz by Zorak w/ Red Chocobo [http://lparchive.org/Pokemon-Quartz/]
Pokemon FireRed [http://lparchive.org/Pokemon-FireRed/]
He did Pokemon Platinum last year, but it hasn't been archived. You need a Something Awful archive account for it.
As said, anything by the Freelance Astronauts- Under Maxwell Adams on the Archive. SAMaxwellAdams is the Youtube Channel.
Lt. Danger's Neverwinter Nights 2 [http://lparchive.org/Neverwinter-Nights-2/] + Mask of the Betrayer [http://lparchive.org/Neverwinter-Nights-2-Mask-of-the-Betrayer/]
Pokecapn + crew's LPs are typically hilarious. Includes Mario Party [http://lparchive.org/Mario-Party/] and some [http://lparchive.org/Sonic-4/] of [http://lparchive.org/Sonic-and-the-Black-Knight/] the [http://lparchive.org/Sonic-Colors/] various [http://lparchive.org/Sonic-The-Hedgehog-2006/] Sonics [http://lparchive.org/Sonic-Unleashed/]
Also the [http://lparchive.org/Dwarf-Fortress-Boatmurdered/] Various [http://lparchive.org/Dwarf-Fortress-Headshoots/] Dwarf [http://lparchive.org/Dwarf-Fortress-Syrupleaf/] Fortress [http://gemclod.goondorfs.net/] Compilations [http://forums.somethingawful.com/showthread.php?threadid=3445758].
The Archive [http://lparchive.org/]