As the old saying goes, “with tragedy comes opportunity.” For JAY-Z, no other year defined that better than 1997.

On March 9, 1997, the hip-hop world suffered the untimely demise of The Notorious B.I.G., who was shot and killed by an unidentified assailant in Los Angeles. A good friend to Jay, Big’s death left a spiritual presence to loom over the music scene. But in his passing came increased attention by the public on who would step up to carry the baton. After all, filling Big’s shoes would require a big album. JAY-Z took it to task.

Before becoming Hall of Fame Hov, JAY-Z in 1997 was still striving to make a name for himself in an extremely crowded New York City rap scene. Part of him getting shine at the time was the skills that he put on full display for his 1996 debut, Reasonable Doubt. The album, filled with jewels like “Dead Presidents II” and “D’Evils,” gave listeners a full-colored introduction to the man behind the flashy and conscious poetics. But while it was easily regarded a classic, Reasonable Doubt was a slow seller. In an effort to build the exposure behind his coveted rap skills, Jay and his Roc-A-Fella Records co-founders Kareem “Biggs” Burke and Damon Dash inked a distribution deal with Def Jam, selling the initial half-stake of the label for a reported $1.5 million. Not long after, 1997’s In My Lifetime, Vol. 1 arrived. But where Reasonable Doubt offered prophecy, the follow-up didn’t quite back up the promise of its predecessor.

On Vol. 1, Jay attempted to mix his triple-beam schemes with pop-star ambitions and while likable (“Where I’m From,” “A Million And One Questions”), in that it stood between street favorite and commercial success (the album peaked at No. 3 on the Billboard 200), the effort failed to match expectations by critics and the general public. After all, you can’t have gems like “Imaginary Player” and “You Must Love Me” sit next to “I Know What Girls Like,” easily one of the worst songs in Jay’s entire catalog.

But in the fight against the try and fail, Jay eventually got his mind right.

“I went low-key, but now I’m back, it’s on muthafuckas,” he defiantly raps in the closing seconds of “A Million And One Questions” on In My Lifetime. To shake off the mixed response, Jay redirected his focus and retained his core the best way he knew how. Months before he would stretch the game out on Vol. 2… Hard Knock Life, Jay treated 1998 with a little straight-to-home video magic called, Streets Is Watching (released May 12). Turning his loss into a lesson, Hov stepped in front of director Abdul Malik Abbott’s lens for his rap (and more gritty) equivalent to Michael Jackson’s own Moonwalker. Delivered “strictly for the fans,” as Dame Dash would put it, the 60-minute film pulled out the best moments from Jay’s imperfect sophomore gem (“Streets Is Watching,” “Where I’m From”) and constructed it with a series of wildstyle vignettes. There were shootouts, stick-ups, and foreplay all soundtracked by the sounds of Vol. 1 and Reasonable Doubt. To counter its haphazardness, Streets Is Watching is gelled by an inconceivable charm.

The film is far from Academy Award-worthy status, but you must still put some respect on its name. In it, we see a visual complement to Jigga’s blueprint. We see a team of young black entrepreneurs utilizing their assets and putting their respective talents on the table for the better. Together, Jay, Dame and Biggs formed Roc-A-Fella as a means of protecting their integrity and art. They were tired of greedy record labels stifling burgeoning artists with corporate shenanigans, so they funded their own record company and released their album on their own terms. How’s that for self-made? To open up their market, the trio smartened up and got Def Jam Records to buy half a stake in Roc-A-Fella to distribute their own albums—again, on their own terms. In that regard, Streets is Watching captures this spirit of Entrepreneurship and Self-Made 101, illustrating a testament to the American Dream.

It isn’t where you came from, but where you’re going that counts. For Jay, Streets Is Watching in all its low-budget glory, may have been perceived as a mess, but the success story that followed its arrival is what makes it a diamond in the rough. Turning tragedy into triumph, and losses into opportunities, this film is a testimony to the American Dream.

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