There's more stuff in the email, but I'm focusing on the part that I quoted.
Once every few days I think about the "(no relation)" joke and how to me it's a pretty perfect joke. The depth of that joke -- a stranger introducing himself to a stranger with the same last name assuring him that they're not related in a common shorthand -- has always stuck out to me. I am prepared to share an essay's worth of words to explain why I love the efficiency of that joke so much if anyone wants it, but I won't bog this down with that. I only bring it up to say the first nine words The Jacks of Life ever wrote to me contained one of my favorite jokes of all time. And now that that's been stressed, I'd like to go further and say that the joke, with all of its importance to me, is still probably the least important aspect of my introduction to Jack. (Or, again, a nickname he preferred to go by, including but not limited to "Humpin' Jack Splash," which is what he insisted I call him when I officiated his wedding.)
I was a 21-year-old little baby boy kid when I'd first submitted two articles to Cracked, and one was decent and the other was complete dogshit that displayed a fundamental misunderstanding of what Cracked was doing at the time. (Again, we literally did not have an original video component to the site. Why would I write a sketch that REQUIRED William H. Macy as a performer in it, by design?) Objectively half of what I'd done was unusable garbage.
Good Ole' Oyster Jackers has a unique ability to find what is good about a thing, anything, and zero in on it. Even if a thing is literally 50 percent awful, Cactus Jack can find the good parts and shine a light on them because he is attentive and patient and thoughtful. Anyone who has ever been on an editorial call or in a brainstorm room knows how easy it is to discard a half-baked idea and move on to the next thing; the comedian's resting state is "That didn't work, let's keep trying." Knick-Jack Paddy-Jack Give a Jack a Bone stands out for being the one to say, "Wait, let's find the best part about this and celebrate it." He brought that spirit to every single editorial meeting and pitch he ever came across. Some of those meetings were three hours long and the rest of the people on the call were just looking for reasons to turn down a pitch, but he was the one willing to find the good and save it.