Jail is not a funny subject unless it’s all related by Aaron McGruder.

With the well documented trouble that Riley gets into at school, it’s not a surprise that Granddad’s necessitated to head down to school for a meeting with the principal. Huey’s inclusion in violence, though, seems odd and probably included simply to push the plot forward. Either way, the boys are offered one of two options: expulsion or a trip to prison as a part of the Scared Stiff program.

Part of what makes "A Date with the Booty Warrior" so ridiculously funny is that it dove tails with the long running joke about Tom’s fear of going to jail and being raped – there’s an entire episode about it. Here’s another.

After enrolling in something akin to AA, but for those in fear of being anally raped in jail, Tom decides to tackle his fear head on and accompany the boys to prison. His decision is met by total disbelief – most folks figure it’s a good step, but perhaps too soon in Tom’s subduing of the problem.

Disregarding other’s apprehensions, Tom, Huey, Riley and a handful of white kids head to the prison for a tour and a lecture. The scenario grants Uncle Ruckus, who apparently works everywhere in the city, but doesn’t get paid most of the time, an avenue to crack wise about the future of those white kids while denigrating Huey and Riley. It’s to be expected, but in this clever scenario, the jokes come off as almost fresh and get delivered in tones that warrant immediate laughter.

With only a few episodes left this season, it’s going to be rather difficult for McGruder to top this right here, but hopefully he’s up for the task.

Best Moment: Where there bad moments? Nope. But when Tom takes the kids on a Scared Straight tour, the ensuing discussion of how important ass is in prison can’t be surpassed by any other segment in the episode. Watching Tom’s reactions and eventually his fleeing should easily be figured as a season highlight – if not an highlight of the show’s three seasons. It was that hilarious.

Notes: It seems odd that Riley hasn’t ever become slightly interested in his brother’s overt political ideas. That’s probably as a result of the characters needing to juxtapose one another coupled with the allure of tough-guy stances, but interesting none the less.

Episode Rating: 4.5 (I’d have a hard time giving any show a perfect score, but this one got pretty close.)