My 4 Favorite Songs On Reasonable Doubt #RD20

Today marks twenty years since Jay-Z released his debut album, Reasonable Doubt. A landmark achievement that rests in the hall of fame with other legendary East Coast rap albums. It’s hard to imagine Jay as a 26-year-old hustla putting out his first album, and trying to shake off the Hawaiian shirt persona he developed with Jaz-O. The Jay-Z on songs like Feelin’ It & 22 Two’s is drastically different than the Hov we hear on the All The Way Up Remix or the one we see in Lemonade. ’96 Jay still had a foot in the underworld. He only saw rap as a side hustle and didn’t quite understand his gift as an artist. He collaborated with some of the greatest producers of the 90s to create this timeless piece of art that rivals Illmatic and Ready To Die. Going through the tracklist and only choosing four favorites is tough, but here are my favorite tracks off Reasonable Doubt.

Cashmere Thoughts

“Return Of The Jedi, From Rio De Janeiro To The Red Eye, Yet I, Still Feel The Need To Be Fly”

This is the bravado Jay is known for. He was doing it better than most even back in ’96. His flow is smooth, but the rhyme scheme is intricate and complex. This is what makes him so special. Having a great beat from Clark Kent doesn’t hurt either.



“9 To 5 Is How You Survive, I Ain’t Tryna Survive, I’m Tryna Live It To The Limit & Love It A Lot.”

I wonder if Jay knew what he was doing when he made this song. Did he know that people would be referring to this track 20 years later in an attempt to connect him to The Illuminati? Was he laughing then the same way he’s probably laughing now? Who knows. We do know that this song is cold and merciless, exactly how Jay, and many of his contemporaries, wanted to appear at the time. What makes this take interesting is how sad and powerless Jay seems while committing these evil deeds. It’s depressing when he says “In time I’ll take away your misery and make it mines…” It’s as if Jay, and others have no control over the evils that they do for fortune. What’s even more ironic, is that he knows that he may never enjoy this wealth he’s willing to kill for. This is what made his gangsta rap more sophisticated than most.


Politics As Usual

When It… Come To This Cheese, Y’all Three Blind Mice

This is what a New York drug dealer hears when he ends up in Las Vegas in the 80s. Despite celebrating, despite the successes, it’s all business… and in Jay’s case, regrets. While bragging about his “matching VSR” and “huge Magnavox” he’s thinking about what he’s sacrificed to get here. “10 years later got me wise  still can’t break my underworld ties.

Can I Live

“I Rather Die Enormous Than Live Dormant That’s How We On It.”

Can I Live is easily one of Jay’s greatest songs ever. The undisputed highlight of the album, Can I Live is Jay-Z at the peak of his potential back in ’96 and the song foreshadowed the great things coming. Jigga is known for great lines and this song is full of them. “I keep my head, both of them, where they’re supposed to be.” “These days a brother gotta admire me from four fiends away.” “I stepped it up another level/Meditated like a Buddhist.” It’s like he was crafting Twitter-ready phrases before the internet.

Everything is so perfect. The production, done by Irv Gotti, is magical. A perfectly looped sample that captures the boss don, smooth mafioso style Jay is trying to capture. Combined with dense, thoughtful and well-paced lyrics. What more could you ask for from a young Brooklyn dude trying to make his next buck? This song reminds me why I love Jay-Z.

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