A few of my favorites that I haven't seen crop up here yet:
Makes me wonder if Chris was one of those kids who thought that this was the real Santa or if he was one of the "helper elves" that went to malls and stuff. Furthermore, I wonder if Chris even ever noticed that he was seeing different Santas (face recognition issues, et al). Also it seems even from a young age he wanted to STAY STRAIGHT and did so by eating Chick-Fil-A.
I like that there are so many pictures from this set. You know they were taken in the same day. I just like this one because Chris apparently convinced Barb to pose with Sonic. That begs the question, who is operating the camera? Is it Chris? Did Barb trust him to handle the camera? Was Bob there and simply doesn't appear in any of these photos?
I think Sonic counts as a Chandler on technicality. I'm linking this one because I did shit like this with some of my favorite toys and possessions, too. Mostly nostalgic for me, kind of one of those "these were the most important things to me when I was [age]" kinds of feelings. Shows a more innocent and relatable side of Chris.
I find this "lulzy" only because Bob is rarely seen in a jovial mood. He's usually sitting, reading, or doing something idly in the background. Here he is climbing on a wrought iron fence.
If you've never played Super Mario 64 then you have no idea how hard this accomplishment is. In fact, you wouldn't even know what you'd be looking for. 152 coins in this level is a "perfect", which is damned near impossible. This is "lulzy" to me because I am mentally picturing the unincluded expressions that you just know CWC is making off camera. This picture also shows a close-up of the stuff in the background of that Lego tower photo being discussed: some Disney VHS Happy Meal toys, what looks to be ANOTHER Pizza Hut kid's meal cup just behind said toys, and Sonic 3D Blast currently in the Genesis. Ick.
Also really surprised this isn't here. I see the Love Quest pics here getting a lot of rotation, but this one is my go-to picture I see when I think of Chris. That dejected look as he holds a Pro-200,
one of the absolute worst handheld "games" on the market. Look at his eyes; he knows. He could be upset for any number of reasons, too. Maybe he assumed the games were shit, or maybe he opened it and mentally heard the commercial's "NEVER BUY ANOTHER CARTRIDGE AGAIN" tagline and thought he'd never be getting anymore vidya from Borb for the rest of his life.
Finally, I have an honorable mention picture that I don't have handy. That damned shot-framing hand gesture Coleslaw does at the beginning of every one of his videos.