I had a Rock shirt with "Do You Smell What the Rock is Cooking" on the back, didn't wear it much, dunno what happened to it. I also own, and still wear, a Crazy MAX shirt with the logo on the front.
Before the Benoit incident, for me, the cringing came with how many times Joey Styles said Mike Awesome could die and such.
Yeah, I forgot about that. Complete with Joey Styles lamenting that Mike Awesome's suicide dive didn't really result in him killing himself.
Anything involving Benoit at One Night Stand 05. The aforementioned "Kill that sumbitch" line, the announcers saying "and for everybody who thought ECW was just about blood and violence" when Benoit came out for his match, and I remember quite a few lines of commentary being cringe-inducing in that context.
I loved the big tease with Jim driving to New York and then turning around. "I'm not that guy, we're not that couple" was a great line. And the whole auction thing was awesome. This is one of the best episodes in a while.
Craig pretty much saved the Pan Flute story with his little rants about how the main four are assholes and nobody likes them, and the giant Guinea Pigs were hilarious.