The original "Longest Yard" is one of those fun 70s comedies pitched sharply at the angry young-male audience which is today somewhat obscure because it was made in the 70s, when angry young-male films still sported the "harsh" vocabularly and visual sensibility OF angry young-males, and thus is now unable to be replayed into classichood on TBS. You may, or may not, remember that the film starred Burt Reynolds as an imprisoned former NFL star roped into assembling a team of fellow convicts to play an exhibition game against the prison guards.
Reynolds, viewed as he was at that point in his career as an icon of the old-fashioned alpha-manhood which was visibly dying out in the popular culture of the time, was perfectly cast at the time, and the film (while imperfect) struck a certain cynical chord: The prison as a microcosm of an increasingly socially-regimented (what would come to be called "politically correct") modern society, guards as the ultimate image of The Authorities, and prisoners (embodied by Reynolds) as the rugged American individualist of old, struggling against both to retain manhood and the last semblance of honor.
The remake has Adam Sandler in the Reynolds role, and moves the story to the present where a "rugged iconoclast" like ex-Quarterback Paul Crewe would be even MORE out of place and, thusly, the story should probably be even MORE cynical, bleak and harsh about it's comedy. Especially considering how much more... "dark" our collective view of prison is after "OZ." But, then, you knew that wasn't going to happen: Despite the decidedly R-rated "sophistication" and sensibilities of the average 13 to 18 year-old audience that Sandler caters to, they're barred from R-rated movies.
Thus, we here have a film set in a prison, with a cast that is collective supposed to range from 30 to about 80 years-old, featuring "prison bitches," billy-club beatings, and a football game featuring steroid-juiced guards versus a gaggle of psychos, arsonists and thugs... thats been forcibly nuetered down to only the most broad implications of it's real story and events. In other words: Here's another "PG-13" comedy that's really only in theaters as an infomercial for it's own "UNCUT AND UNRATED!!!!" DVD double-dip six months from now.
Drummed out of the NFL for alleged point-shaving, Crewe is jailed after taking out his frustrations on the expensive car of the haughty society gal who'd claimed him as a trophy husband. The warden, (James Cromwell,) wants him to get the cons together as a test-team against his semi-pro Guard squad. At first he's just going with the flow, but wouldn't you know that Crewe finds identity and redemption in turning his motely crew into athletes. And would you be surprised if I told you that, at the height of this redemption, Crewe is suddenly faced with a choice that not only mirrors his past indiscretions but might even enable him to atone for them? Didn't think so.
The biggest issue here is that the filmmakers seem convinced that EVERY sports film automatically must be eventually uplifting and heroic... and thats against the nature of the material here, which is only partially-heroic but mostly belongs in the realm of angry cynicism: The whole edgy appeal of the prison movie genre, the graying of societal structures and concepts of "good" and "evil" in an entire community of criminals, is swallowed up in a structure that wants to be (the teen-boy comedy version of) sentimental and life-affirming. It just doesn't fit: You can't make "Saving Private Ryan" out of "M*A*S*H*".
This isn't to say that it's not funny, it is, but completely forgettably so: There's nothing here that sticks, not even when things start to get all "serious" in the last act. Most of the time, the film is underrcut by the "mandates" of being "an Adam Sandler film" instead of "a film with Adam Sandler": Fat jokes, gay jokes, genital-slapstick and the obligatory Rob Schneider "you can do it!" cameo all show up to distract and derail. Reynolds is also here, now aging gracefully and playing a character who must be pushing 70 but still looking more like an NFL player than Sandler can manage to, another BIG flaw.
Not bad, not even awful... but just not much at all, sadly.
FINAL RATING: 5/10