Jay-Z’s ’99 Problems’ Mostly Contains Decent Legal Advice, Law Expert Finds

Jay-Z’s watershed rap hit 99 Problems is undoubtedly the most well-loved track off The Black Album, which in turn is arguably the pinnacle of Hova’s career and one of the best commercial hip-hop albums of all time.

Jay-Z’s 99 Problems also has the side effect of, vis a vis a series of anecdotes, dropping knowledge on a community of hip-hop fans regarding what to do in the event of a police stop.

While the song has been controversial due to some implied misogyny — which Hovito himself denied in a lengthy discussion about 99 Problems on NPR’s “Fresh Air,” — it covers a range of topics, from haters who dismiss his music as being about “money, cash, hoes” and haters that try to induce him to commit acts that will land him in jail. (But the constant refrain suggests that despite all these weighty woes, he still feels for a dude who has problems with his woman.)

The most recognizable verse of Jay-Z’s 99 Problems, however, is the second, in which Hova describes a police stop circa 1994. He describes weighing whether to “bounce,” and “put the pedal to the floor” due to quantities of contraband in the trunk, but ultimately decides to accede to the officer — a smart decision, says law professor Caleb Mason in Saint Louis University Law Review.

Mason continues:

“This may be the hardest choice perps face (until they have to decide whether or not to cooperate), but there’s only one answer: you are always better off having drugs found on you in a potentially illegal search than you are fleeing from a potentially illegal search and getting caught. The flight will provide an independent basis for chasing and arresting you, and the inadequacy of the quantum of suspicion supporting the initial attempted seizure will not taint the contraband discovered if there is an intervening flight. Law students: practice explaining the preceding sentence to a layperson. Smugglers, repeat after me: you have to eat the bust, and fight it in court.”

Mason, who does a point-by-point takedown, also addresses Jay-Z’s suspicions of profiling, as well as his decision in the song to plead ignorance as to why he had been stopped. (Sarcastically asking the cop whether it was because he was “young” and “black” and his hat was “real low” are, Mason says, all likely and legitimate reasons for such a stop:

At the time the song takes place, the New Jersey State Police had an active “drug courier profiling” program that would absolutely have included the observable facts
here: Jay-Z was: (1) young, (2) male, (3) black, (4) wearing attire favored by
drug dealers (the hat way down low), (5) driving an expensive car (in the video), (6) traveling on I-95 (the primary route for bringing drugs into and out of the city).

He continues:

Such profiles are of questionable validity as the sole basis for a stop, but there is no constitutional reason why they cannot inform an officer’s subjective determination to stop someone if there is objective probable cause for the stop (for example, speeding).

The entire (fascinating) legal takedown of Jay-Z’s 99 Problems can be read online, and you can watch along with the clip below:


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