The only other movie I remember vividly with the protagonist fearing his upcoming time spent in jail, was in Spike Lee's powerful drama 25th Hour, where we follow Edward Norton's character in his final day of freedom before being sent to the slammer. In Big Stan, Rob Schneider's crooked time-share conman Stan got arrested in the opening minutes for fraud (and you might think it's for racism), and spends much of the first act mulling over the fear of getting raped in jail, for not being part of any gang, and a first timer wussy who's easy target for the lonely tough guys behind bars.
Thanks to his crooked lawyer Lew Popper (M. Emmet Walsh) and the crooked system (from the judiciary right down to the prison warden, who as the movie states, are always made to look like dicks anyway), he gets six months off before he has to present himself to the courts to begin his sentence, in in this period of time, tries his best to look "undesirable". Help comes in the form of The Master, played to good campy effect by David Carradine, star of the 70s Kung Fu series, whom I last saw in Quentin Tarantino's Kill Bill movies playing well, yet another stereotyped kung fu master.
Thus begins the tried and very tired formula of the kooky training regime with strange food and diet, coupled with near impossible feats like titty-weight training. Granted there were some genuine sight gags, but sad to say they all get confined to this particular sequence. The trailer would have already spelt it all out for you, and suffice to say that the best bits were already inside. The story by Josh Lieb seemed to have run out of steam even before the mid-way mark, where Stan had already entered the jailhouse, and asserted his tougher than tough, no nonsense, keep away demeanour by punching the lights out of the meanest rapist in jail, and a few others.
If you're looking for end to end laughter, then you're likely to be bored once Stan becomes head honcho in getting some respect in jail. With that out of the way, the movie degenerated into series of cliches, and the usual nasty warden with nasty plan routines. It didn't help that supporting characters here were stereotyped into playing stereotypes, conveniently split into the different cliques and clans.
Directed by Rob Schneider himself, his films to date has somewhat been of a hit and miss for me. Lending his prowess to supporting roles like in You Don't Mess With The Zohan and Click, I thought he usually fared better in those, unlike having to carry the movie solely on his own, ala Deuce Bigelow and The Benchwarmers. What I found out unfortunately is that they usually start off strongly with quite a unique premise ripe for the cracking of some insane jokes, before fizzling out halfway and coasts through some predictable drama to the finale.
Still, some laughs are better than none at all, so if you really feel that you need some light hearted medicine, then you'll find some joy in the beginning, but that's all.