How to engage in a rap off and lose.

In one notable seven year old journal entry, I wrote about  my desire to be Lisa “Left Eye” Lopez, the now deceased member of the group TLC. An excellent female rapper, Lisa inspired me to strive to achieve her level of linguistic genius. Instead of the usual male rapper reliance on sexual innuendo (think: “Candy Shop”) or outward vulgarity (think: “Candy Shop”), Lopez managed to rap about issues in a coherent, clean, and effective manner.

However, unlike Lisa, I led a sheltered Jewish upper middle class girl existence. Issues of drug abuse and gang rape were far removed from my reality. My biggest struggle was whether to order the latte with skim or whole milk. And while such caffeine-inspired struggles have merited youtube videos, they were certainly not the issues I thought or sought to rap about.

I subsequently gave up on my musical aspirations and moved onto bigger and better things, like blogging. But then I moved back to New York and began a babysitting business, which has provided me the opportunity to sit for some notable city toddlers.

One such toddler, the son of a Chicago rapper, reminded me of my childhood aspirations when he challenged me to a rap off. “Let’s see if Little Miss Pasty knows about life in the hood.”

Not one to pass on a lyrical challenge, I countered, “Well, Chocolate, my finances resemble more of the hood than yours ever will. Let’s do this.”

The toddler then suggested we see who could rap “Stronger” better. And before he could even say go, I began reciting the entire Britney Spears song by heart. He did not follow, and after uttering, “My loneliness ain’t killing me no more,” I paused.

“What the hell was that? That ain’t the song. That some pop ditty you just cooked up.” Some. Pop. Ditty. that just happened to encapsulate my middle school existence. But that also, on second thought, was pop, not rap, and therefore not the “Stronger” the toddler intended to employ in our little contest.

Yes, the toddler was referencing Kanye West’s “Stronger,” a song similar in sentiment to that of a Lisa “Left Eye” Lopez rap– a rap about overcoming obstacles, not tweenage heart break. The Pasty in me had just been revealed in all its white girl glory.

I tried to redeem myself in an R&B sing off, inspired by our film du jour: The Wiz (1978). If any white girl could channel Michael Jackson and Diana Ross, at the same time, it was your truly. I even added the requisite cinematic footwork:

Sadly all my little chocolate friend could do was laugh… and reply, “Honey, stick to your day job.”

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