I just now saw Wordplay but The Aristocrats about a year and a half ago when it was first released and haven't written about it until this post. The reason I'm combining them is that they share the same flaw of almost no historical curiousity and both could have benefitted greatly from the help of a real journalist. For The Aristocrats this is a serious but not crippling flaw but it nearly sinks Wordplay.
Start with the more interesting film. By now anybody reading this will know what The Aristocrats (Paul Provenza 2005) is about but what seemed so odd to me is that there are a few references to the origin of the joke and some urban-legend-ish stories about it but almost nothing concrete. Interviewees mention a few times that it originated in vaudeville which is clearly wrong; there's absolutely no way the joke as it currently exists was used in vaudeville and probably not even in burlesque. There is a possibility that it was a vaudeville joke with a different center section but whether or not that's the case nothing in the film shows that the slightest attempt was made to research this. There are vaudeville historians, books and even people with long memories but none are consulted. I find it just as easy to believe somebody in the 50s made up this joke and then claimed it was from a few decades earlier. For instance, Phyllis Diller mentions the first time she heard the joke and the obvious questions are when? Who told it? Where? Do you remember how it went? What was the second time she heard it? The film just presents some rumors, a few of which--such as Michael O'Donogue telling it for a full hour--are clearly lies. Similar lack of documentation with the story that the joke was commonly told only among other comedians and not in public. Again, there's little to support this even though most reviewers accepted it as fact. There are reports (not in the film) that Buddy Hackett told it during a public performance in the late 50s and also several years later during a commercial while taping The Tonight Show. I don't know whether these are actually true or not but are certainly plausible enough that this should have been addressed.
A problem that cuts closer to even what the film is actually trying to do is that the joke is presented intact so few times. There's a lot of talk about this being like jazz where different comics improvise in their own styles on set changes so there should be much more presentation of that. Instead there is a composite telling, a few more or less straight renditions and then some eccentric or unusual takes (mime, cards, reversals, etc). Hiding comic invention is not the best way to celebrate it. There are also some odd choices. The Onion staff has no business being in here and are just embarassing. Chris Rock clearly was chosen only for marquee value since he contributes nothing to the film. A few others seem chosen just because they're filmmakers' buddies.
Wordplay (Patrick Creadon 2006) is like a Sunday newspaper feature that's amusing but leaves little lasting mark. Creadon and co-writer/producer Christine O'Malley seem more fascinated by the celebrities they've hooked and the mostly uninsightful remarks from the other crossword fans than any serious or even quasi-serious exploration of crosswords. Admittedly the celebs are mostly pretty solid with Jon Stewart and Bill Clinton being good interviewees (while the Indigo Girls really need to fade away so we don't have to put up with them any more) and the non-celebs fairly personable. Daniel Okrent, though, is the one that should have been given far more screen time. He has the most insights and the least fluff of perhaps anybody on screen. He's the one that claims musicians and accountants/number people do the best because they're trained at recognizing patterns, which whether strictly true or not does point at something ignored otherwise in Wordplay. That's the idea that solving crosswords is somehow related to intelligence. Sure it does take some smarts and at least a basic education but more important are crossword experience and such factors as this pattern recognition. At least they didn't bring up the old idea that crosswords increase vocabulary which can be easily disproven. As dubious as I am of expert opinion in documentaries this one could have used a little bit of the context they could provide about puzzle solving in general or language use or even obsessions. (My guess is Creadon & Co wanted solvers to be normalized and not freak show material.)
But that's where the lack of historical or almost any other perspective comes in. There's some mention of the NYT's first crosswords editor and how she made them popular but that's about it. Who actually invented them? Were they popular everywhere or just New York? How popular? What were some sample clues from that time? How have they changed over time? But then the film is so exclusively about the NYT that it wouldn't be surprising if the Times funded it as a promotional tool. There's also no mention made of British-style crosswords or if there are other varieties. And little about the mechanics. How are puzzles solved? Do people memorize words like Scrabble players do? What exactly makes for the different difficulty levels? What about people who can't complete them in a few minutes? What do they get out of these? These latter solvers are the ones that would make the bulk of the readership but I don't think a single one is interviewed and except for letters to the editor go mostly unrepresented. One of the best segments is actually in the DVD's deleted scenes which is a handful of puzzle creators describing specific puzzles. This is fascinating nuts-n-bolts stuff even though I'm still curious about the finish of constructing a puzzle: Anybody can do the opening but what does it take to make it really work. Another of the best sections is when we see the start of a puzzle being constructed then a montage of the various interviewees solving that same puzzle.
This leads into the worst decision in the film: the tournament. I'm sure if you asked Creadon & Co. they would say they were lucky to have such an event to tie it together but really this is a very undramatic tournament and not simply because it's not visual. There are no playoffs (anybody can enter), there's no training and it seems too reliant on luck. In other words, just not very competitive at least for people outside the event and while it's easy to feel that the winner of the Scrabble tournaments is one of the best players in the game these crossword contestants just seem like people who had the spare time to head to the tournament. But there's something American about preferring to watch horse races than thinking; after all that's how elections are now covered and even something like weekly film box office rankings when in fact there's no real competition (since only a handful of films have even a remote chance at the top spots). Wordplay ends up more or less as a first half of interesting fluff and a second half of seriously tedious tournament coverage.