These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Anwar is 50 Cent's biggest fan who ends up in an internal struggle when Wilder forces him to try and kill his idol (though at that point in the game Chip and Ironicus seem to have confused him with Amal, who actually does call himself 50 Cent's biggest fan.)
Chip thinks Otacon's codec messages which overlap with gameplay means that Otacon is actually trying to Let's Play Metal Gear Solid 4 himself.
When Snake is running through a hallway late in the game, remembering various lines already said by other characters, one of said lines is Snake's own "you were the lightning in that rain" comment. Chip interprets that one as Snake remembering things he's said that he's embarrassed about and wishes he could take back.
During the Metal Gear Solid 2 Let's Play, where at different points during the game the video loses focus from the actual game to him playing a demo of a Cabela's hunting game. It tends to happen when Rose addresses Raiden as Jack (the main character of the Cabela's game is also named Jack).
Chip's dad (aka Dad Buster) wandered into the recordings of No More Heroes and rambled about Star Trek and immediately stole the show. Since then, Chip has shared many anecodotes relating to his father (for example, watching Chip play MGS3 and thinking it was Harry Potter).
Ironicus admitted to liking Mil, because he looks like "that one Sonic the Hedgehog fanfic self insert character."
Ironicus states repeatedly how much he loves Con and Mask de Smith in Killer7, as well as Travis (thanks to being the only Remnant Psyche that even remotely tries to make sense) and Yoon-Hyun (because of the double bird he's always giving you, bolo tie be damned).
Monsoon from Metal Gear Rising. Both Ironicus and Chip both actively wonder how a solo DLC starring him would be insanely awesome and Chip seems to regard him as one of the better bosses in the game.
While making fun of Nathan Drake's Kleptomaniac Hero tendencies, Chip imagines Drake finding a Canadian penny and claiming it to be valuable treasure. A few months after that video was released, the Royal Canadian Mint took the penny out of circulation, and thus, given a decade or two, it will be a rare treasure!
At one point in MGS3, Chip mentions that he wishes you could throw porn magazines rather than having to place them. Nearly four years later, Metal Gear Rising: Revengeance comes out and lets you do just that with the similar-in-concept photo frames.
In the same LP, Chip says that "People in Metal Gear, they have special spines... Nanomachines." And then came Revengeance.
During the LP of Metal Gear Solid: Peace Walker, Snarkcookie notes that Big Boss aims with the eye that he lost, so Chip jokingly proposes that he has a "Phantom Eye" that can see. A couple of weeks later, The Phantom Pain was announced, and was later revealed to be the next title with Big Boss in it.
Memetic Badass, Memetic STD God: Sully, oh so much. Early in their first Uncharted LP, Ironicus says that he's so well-hung and so infirm that he can only get an erection through industrial equipment, including a pulley system. Lampshaded early on in the Uncharted 2 LP.
General Ironicus: Sully's already the best thing in this game and he hasn't even shown up yet!