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Throwback Write-up #7: Jean Grae - Bootleg of the Bootleg
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Artist: Jean Grae

Album: Bootleg of the Bootleg


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Background

Jean Grae is a lyrical MC born in Cape Town South Africa before moving to New York City at a young age. As the daughter of two jazz musicians (including a mother that managed her own label), throughout Jean Grae's life art and music was part of her lifestyle. Whether it be starting off in dance, starting a career as a producer or her eventual rise to being an MC.

One thing that has always defined Jean Grae's life is her competitive spirit which she cultivated to push herself as far as she could no matter what work she was perusing. When she made beats she'd focus everything on making them the best, and this only continued when she started her rap career in the mid 90's.

After Originally using the name 'What? What?' for the first few years of her career she decided to change her name to something more self-reflective of who she is. The name Jean Grae hatched from her love of comics and specifically the X-Men character Jean Grey.

A few years of demos and small releases eventually set the stage for her 2002 debut album Attack of the Attacking Things. With a heavy focus on lyricism and a cold delivery Attack of the Attacking Things left both critics and fans alike excited for what could possibly come next, and after only a little over a year we would get that release with her EP Bootleg of the Bootleg.


Album Review

Preface: I will be discussing tracks based on how they appear on the deluxe version of the album. Both the original and the deluxe share the same length the deluxe edition just splits the 45 minute long Chapter One: Destiny into 11 separate tracks.

As we discussed earlier one of the biggest motivating factors for Jean Grae is her competitive nature and tenacity to be the best. She makes no better case for this than on the opening track 'Haters Anthem'. We are instantly introduced to Jean Grae's exceptional ear for production bringing some killer boom bap percussion along with an excellent baseline before quickly hitting us with her punchy and cold style of rap she's known for. It's a song where Jean Grae is un-apologetically putting herself on top. At this point in her career she knows her talents are above that of her pupils and in true hip-hop fashion she's going to let everyone know.

While Jean Grae is certainly exceptional from a technical standpoint and loves to boast about her talents; she doesn't take long to get into the meat of some lyrical substance on the following track 'Take Me'. A track focused on Jean Grae's troubled relationship with God.

Lock and aim and I'm dropping my frame quick when I pop in the brain

And if God's omnipotent,

will he slip in and change

And move the pistol so it shoots out of range and the lead whistles?

(Baby) Maybe he's just playing; it'll ricochet

And cripple me strictly for questioning, give me life to the pain

'Take Me' offers the other side to the coin of 'Haters Anthem'. Instead of being a song of immense confidence it's instead a song of vulnerability where we find her in a deep depressive state where she feels self-destructive attitudes taking over her life afraid of how it could potentially lead to a shortened life. Frustration over the negativity surrounding her makes her question the meaning of life.

The sadness expressed on 'Take Me' gets complemented well a few tracks later on 'My Crew' which focuses on the love she has for those around me and her dream to see them succeed. Jean Grae is certainly at least somewhat disappointed in some of the decisions made by those around her, but above all else her goal is to give them the support they need to get over their inner demons.

All of this comes to a head on the track 'Chapter One: Destiny' where Jean Grae is playing the character of a contracted assassin and a piece of their story including the start of one of their jobs and the eventual betrayal by their contractors. This character is expanded upon a few more times in Jean Grae's discography on future tracks like 'Football Season is Over'.

After this point this album shifts into being heavily focused on her rapping beats that other rappers had previously made famous. Giving it more of the feeling of being a mixtape. Despite the change in styling it fits right in, and she performs as well on the production as you'd imagine from someone of Jean Grae's caliber.

One of the highlights on this part of the project includes 'High' which samples the beat off of Nas's track 'Purple'. Jean Grae takes a lot of the themes Nas built on around drug culture and builds upon it with her own thoughts with as much tact as we've come to expect throughout the tracklist.

Along with this we get her take on another classic artists materiel with the track You Don't Know (uses the same beat as Jay-Z's U Don't Know) where we get more insight of her view on media and how focused they are on putting artists like herself into categories rather than respecting them based strictly on ability. Which is something she has discussed a lot in interviews in speeches including her distaste for the terms 'female rapper' and 'FEMC'. Which is something that really isn't discussed much on the project outside of this. Whether or not the fact that she is a woman potentially puts her at a disadvantage in the industry her goal is to force people to respect her regardless because she wants her rap to speak for itself more than anything else.


Conclusion

Bootleg of the Bootleg is a fantastic project that really highlights Jean Grae's excecptional talents as an artist. Her lyrical ability and sharp one-liners can go up against anyone, and I believe this project is a great example of that. It's large variation of topics and sounds with incredibly rich and punchy production leaves it as one of my favorite hip-hop projects of the early 2000's.


Favorite Lines

No, Jean's not hard now, Jean hasn't changed

I was 18 on the first record, I've just experienced the game

Not a thug, not a drug seller, not a gun shooter

Not a stripper, sex symbol, or anything you're used to

Marketing nightmare, I don't fit into categories

I just rap, make beats and shit and sleep all these stories

You Don't Know

I represent for a nation. Thought we was in it together

But I guess it gets strange when money rains in sunny weather

Tougher than leather? We're weaker than glass

And shattered on the side of the road. Try to get a ride,

but pass each other fast

My Crew

Suppose you only used to chicks who use they tits to boost sales

And boot males who switch the crew they with but really fails

Cause rap fans are finicky, your approach is gimmicky

So your turn's over fast, like a young man's virginity

A Little Story


Discussion Questions

  • Is Jean Grae an artist you were aware of prior to ths write-up? If so what were your thoughts on her music? If you weren't aware of her music do you have plans to give it a shot?

  • Jean Grae's output in terms of music has slowed down in favor of other artistic endeavors including books, podcasts, directing, and more. If she were to ever return with a new full length solo-rap project what direction would you hope for?

  • Where do you see Jean Grae fitting in with other MCs in the early 2000's?

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