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The 20 Best Jay-Z ’99 Problems’ Illustrations

Ali Graham

Even for a world famous rapper who pocketed another milli before his album even hit shelves, Jay-Z has his problems (99 of them, to be exact). On his Tumblr blog, which he updates on the daily, illustrator Ali Graham takes a look at exactly what is niggling at the Jigga Man.

From to wanting to be forever young and getting poor table service, to envying other guys’ beards (what up, Rick Rubin) and not being able to wipe that pesky speck of dirt off his shoulder, it’s a hard knock life for Shawn Carter. But hey, at least a b—h ain’t one of his problems, amirite?

Here are our 20 favorite problems of Jay-Z’s in all their illustrative glory.


Broken Umbrella (Ella, Ella)

Jay-Z 1

Yeah, but look who you've got holding it.



Jay-Z 2

Try telling that to Yeezus.


Beard Envy

Jay-Z 3

When you've got "whiskers like a rat" (word to Nas), you're bound to be extra jealous of a mighty face bush like Rick Rubin's.


Radio Don't Play My Hits

Jay-Z 4

It's 2013, Hov. All you need to worry about is selling a million copies of your album to a cell phon -- oh, nevermind.


Unimaginative Branding

Jay-Z 5

Keep Calm and Stop Plagiarizing.


She's a Survivor

Jay-Z 6

They don't call her Sasha Fierce for nothing.


Rollie Don't Tick Tock

Jay-Z 7

And that's the only thing that's "broke" about you. Jeez, quit complaining, Jay.


Dead Presidents

Jay-Z 8

Chill, they're representing.


No Time for Adventures

Jay-Z 9

Cuba doesn't count?


Bad Batch

Jay-Z 10

Jay-Z Pinkman?


Where Brooklyn At?

Jay-Z 11

Here's an idea: Google "Marcy" on one of those fancy Samsung phones you made everyone buy.


Diggers In Paris

Jay-Z 12

"Don’t let me into my construction zone."


I Want to Be Forever Young

Jay-Z 13

Who wouldn't with a KANYE GRADUATION BEAR to play with?!


Too Much Talent In One Room

Jay-Z 14

And Rick still hogged the couch.


One Last Time I Need Y'all to Roar

Jay-Z 15

You should be happy that thing isn't tearing you to shreds, Jay.


Poor Table Service

Jay-Z 16

French-ass restaurants, eh? And hurry up with Ye's damn croissant.


Picasso Baby

Jay-Z 17

"N----s even talk about your baby crazy." We don't blame them.


I'm About to Go HAM

Jay-Z 18

It was all good just a week ago for that pig.


Bad Twerk Ethic

Jay-Z 19

Only in America a Unicorn onesie.


Can't Get Dirt Off Shoulder

Jay-Z 20

"Could you brush it off for me?" No, do it yourself, Hov. I'm sick of your complaining.

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