New Jack City
As drug lord Nino Brown, Wesley should have learned that the simplest little thing can topple your entire empire. Whether it's "forgetting" to file a few tax returns or letting ex-crackhead Pookie anywhere near your computer systems, you have to dot the i's in this game.

Demolition Man
Prison isn't so bad—in fact, it's just a long (albeit chilly) nap until you're eventually defrosted in an age when America has been so pussified that tax evasion might not even be illegal anymore. Downside: cursing and sex are.

U.S. Marshals
If three years is too long a haul to face, you probably could do pretty well on the lam. Just remember that having a federal warrant out for your arrest means you don't want to stick around for the cops to show up should you find yourself in a fender bender.

Major League
According to your buddy, ex-con Ricky "Wild Thing" Vaughn, prisoners get to play baseball all day. And if they're good enough, they can even go pro! See? There's always a silver lining, pal.

Sugar Hill
The IRS is not unlike that slightly unstable brother you got into the drug game with. For a while, they're cool—kind of on the outskirts, not really all up in your grill. Then, eventually, they try and kill your girlfriend and inadvertently shoot you, leaving you paralyzed. In this case, "paralyzed" means "broke as a joke and in the pokie."

Undisputed
The key to surviving prison is to get a hobby. It might be knitting, it might be teaching yourself criminal law, it might be recreational sodomy, or, in an ideal world, it could be the penal boxing system. It'll keep you in shape for your "wink wink" cameo in the franchise reboot Blade: A New Beginning three years from now, where you'll discover that you've been replaced by Nick Cannon.

To Wong Foo Thanks for Everything, Julie Newmar
Well, if all else fails, Wes...you look pretty good in a dress.