General tip, stay away from YouTube, stick to Something Awful. On YouTube people seem to think the point of a Let's Play is the person playing, when the point of an LP is to show off a game you really enjoy. There are a few "YouTube style" LPers who are genuinely funny (The Freelance Astronauts can be hilarious at times, though their stuff is really hit and miss, and pokecapn and his crew who did the Sonic 2006 LP are really funny, and Twisted Pixel even had them do unlockable in-game commentary for The Gunstringer), but most of the people on YouTube are shut-ins raised on the internet who think yelling a lot and spouting memes is comedy gold.
Personally, I'd recommend anything Chip Cheezum and General Ironicus did, as they have a great balance of being informative and being funny. Their LP of No More Heroesis one of my favorites, and Metal Gear Solid 3, 50 Cent: Blood on the Sand, and Killer7are all great as well. Slowbeef and Diabetus (also known for running the YouTube channel Retsupurae, where they record commentary over bad YouTube LPs poking fun at the person and video's technical incompetence) also do some really good LPs, although not everything they do is great. Their LP of Snatcher is another one of my favorites, and Dead to Rights is a riot.
The Let's Play Archive, a site that collects various completed Something Awful LPs, is a great place to start, and you'll generally only run into quality LPs there.
Hope I didn't scare you off by writing way too much about people playing video games for the internet, there's some great stuff out there, there's just so much more shit that a lot of people don't even know Let's Plays can be more than some kid with a camcorder pointed at his TV.
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