The humor in this piece feels a little like hurling darts blindfolded and hoping some of them will hit the target. A couple of them do, sure, and there are few chuckles - but fill 20,000 bytes (!) with anything random, and something will hit the mark. Eventually, it just gets kind of tedious, slogging on and waiting for your next chuckle. I'm sorry this seems harsh, but you've really got to raise the level of consistency of this thing before it goes public.
Here's a list of some of what did and didn't work for me.
WORKED FOR ME:
The expression on Alister Niceguy's face as he looks at his son's hard-on. The whole bit about disguising the guitar as an erection while continuing to practice, and having his father "not suspect a thing", is pretty damn funny. What makes it funny to me is that it doesn't actually mention masturbation - just tells you that he was playing a guitar inside his pants and his father didn't find it unusual.
The idea of combining Sinatra standards with offensive originals. However, you don't really pull it off. "I'm Here to Shock You" isn't a very funny title. Maybe something like (following "I Left my Heart in San Francisco"), "I Left the Tip of my Dick In a Saigon Hooker." Not necessarily that - just something way out in left field.
"The songs -- 1957's "Suck My XXXX," 1958's "We Don't Like Fat People," and 1958's "Masturbating is Fun" -- were banned from the radio and music stores and failed to reach an audience. Yet they somehow managed to become Top Ten hits." I got a little chuckle out of this self-contradictory piece, although the link to "iTunes" ruined it a bit (1. It's anachronistic in a piece where anachronism isn't part of the joke; 2. iTunes reaches an audience).
DIDN'T WORK FOR ME:
Second line: "Least that's what you'd fucking think!" It establishes an inconsistent tone right on the second sentence ("oh, apparently this isn't a parody of a stuffy encyclopedia"). Not good.
The list of how Niceguy spent his life. I mean, it combines a bunch of Eagle Scout-ish things with a bunch of perverted and creepy things, but what's the punchline?
"Vulgar, libelous, slanderous, profane, obscene, shocking, offensive, and politically incorrect, in that order." No, there are much better ways for a stuffy group of critics to make themselves sound stupid.
The song lyrics. Sadly, not funny at all. If they were some kind of twisted parody of '50s standards, that would be funny. But they're just low-grade shock stuff. If it's important to you that Niceguy's songs were incoherent messes of profanity, just telling us that and letting us use our imaginations - or posting a fragment of one, at most - is plenty.
"Wilford took odd jobs off and on, working as a rude waiter who spat on people's food. He got fired after forgetting to fart on President Franklin D. Roosevelt's lasagna a la mode." Way too random. Provides no explanation as to why FDR ate lasagna with ice cream on it, or why he wanted rude waiters to flatulate upon it.
"Moby Dick and the Steamboat Willies!!!!!" is too obscene to be printed? Come on.
The entire "Return to Music" and "Live/stage act" sections. There just weren't any funny lines in them.
Niceguy's cause of death. It looks like it's going somewhere, and then it's revealed to just be a bunch of random stuff strung together.
List of "actors" who auditioned for the part of Niceguy but lost to Steve Carell. ...why is this in here?
Okay, this is what's really killing you. What is the concept of this article? It could work if it were a parody of a biography of a 1950s crooner or standards-writer... but it isn't. It's got all this stuff in it about helping little old ladies across the street, cross-dressing, televangelism, working at Disneyland... it's all over the place. If you can't understand what the joke is about, you won't get the joke.
Prose and formatting:
Most of the prose seems consistently "professional," as one would expect to find in an encyclopedia or biography. Some of it doesn't, like "Least that's what you'd fucking think!" or "He got fired after forgetting to fart." Breaking out of a professional tone into something else can be funny, but you have to establish the tone, first. Anyway, though, the prose is pretty much adequate.
Some of the images are the best part of this piece, I think. The "F-I-N G-E-R P-E-N-I-S" picture was particularly amusing. I liked the "Mr. *ice guy" photo, but it's not captioned ideally, I think - the idea that Niceguy held a job as Rice-O-Roni is perhaps a little too weird to be funny.
Sorry, man, but I think this one needs to go all the way back to the drawing board. Or maybe to the drawing board for the first time, because that's the main problem with the article: it seems like you started writing it with very little plan for what it was going to be. I think the first thing you've got to ask yourself is "What is this a parody of?" Go from there.