Every other Friday, Michael Alexander writes letters to one of the biggest influences on his life: hip-hop.

Dear Big Brother,

No, this isn’t about the record. I know it may go down in history as one of the most complete works of music to ever be compiled, but this isn’t what this letter is about. It’s more along the lines of sadness. A cautionary tale that maybe you could learn from. I know you’re the elder, and by all means I have nothing but love and respect for you, but we’re all prone to error.  And sometimes it’s best to reexamine those errors to avoid potential tragedy.

Lauryn Hill wasn’t so lucky. Maybe shgot too complacent. Arrogance or disregard, whatever it was, it inevitably caught up with her. You would think people are completely oblivious to the story of one of the most prominent gangsters to ever run the streets: Al Capone. No matter how much money you’re making, no matter how much pull or influence you have, nothing comes close to the gang known as the federal government. L Boogie got sloppy and let the government bring the fight to her door, which nobody wants any part of. Tax evasion is the charge that’s  landed her in jail for around three months. Her agreement with Sony, her label, was for five songs and $1 million, which was supposed to save her from going to jail. It didn’t. I heard her newly released single “Neurotic Society,” and it seemed rushed. She even acknowledged on her Tumblr the deadline she was facing to release the track. (It’s weird. You see how dependent we’ve become on technology? We won’t really believe something is authentic or not unless it comes from a verified Twitter or Tumblr account.)

To me, her downfall is a modern-day tragedy. I know you’re rolling your eyes at me, Big Bro, muttering to worry about my affairs and leave others’ alone. But you of all be people should remember what happened when Moms let me borrow her version of The Miseducation of Lauryn Hill. Ok, I lied at the start. This does have to do with the CD. It’s impossible to separate an artist from their most prominent works. You think Da Vinci, you think Mona Lisa. Michelangelo, Sistine Chapel. Chappelle’s Show, Dave Chappelle. You may try, but one’s best work is forever associated with them until their final chapter is complete.

At the time, she had the video out for “Doo Wop (That Thing),” and I was bugging out because she was portraying two people in the video at the same time. It seems silly now, but I was fascinated to see such a thing. That was really the only song I was aware of before listening to the album. I felt foolish after track 16 ended, and even more foolish in undergrad when I revisited it. I just could never fully grasp the magnitude of how perfect that album was. It was my personal “holy shit” moment. We’ve all had that moment at least one time in our lives listening to music. It’s where you’re eyes essentially glaze over, your ears reach a state of ecstasy and you wish whatever you’re listening to never ends. Miseducation has that power.

Maybe that’s what’s really bothering me. Maybe it’s the fact that younger generations of music enthusiasts haven’t had the same luxury in experiencing Ms. Hill’s first record. They may have only heard about L Boogie because of her legal complications and turn a blind eye to her past work. I haven’t even mentioned her accomplishments with the Fugees, which are an entirely different subject for another day. I know you can’t save everyone and you can’t force people to like the things you like. But who dislikes greatness? Who is repulsed by happiness, pain and hope manifest as a compilation disc?

So I write to you, Big Brother, with hopes that the tragic story of Lauryn HIll’s legal mishap is one she grows from. The selfish part of me is always looking for her to release new music. But it just isn’t the same if her whole heart isn’t into it. Maybe you could talk to her for me, maybe even give her this letter. I know I’m just one of many fans who remember the joy that was synonymous with a Lauryn Hill track. Who would’ve known The Miseducation of Lauryn Hill would turn out to be more than just a title.

From your little brother,

Mike