Last December, Brandon Scott Gorrell compiled a notional list of Jay-Z's storied 99 problems. It seems pretty plausible to me:

52. Confusion regarding how frequent one should use Q-tips to remove earwax, due to information he read that stated, more or less, that Q-tips were damaging because earwax had specific, important functions to ear health and bodily orientation and that the removal of earwax simply stimulated the production of more earwax, rendering Q-tip usage asinine.
53. PayPal terms of service and customer service equally horrible and difficult to understand.
54. Still unable to defeat final boss on Nintendo’s Super Mario Bros. 3.
55. Quickly disintegrating upkeep of dental hygiene due to feelings of meaningless and apathy.
56. Navel lint.
57. Confusion regarding the moist towelettes vs. dry toilet paper debates via recently hearing moist towelettes were for some reason bad.
58. Trouble discerning which types of socks are in fashion.

A Speculative List Of Jay-Z’s 99 Problems (via JWZ)

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I write books. My latest is a YA science fiction novel called Homeland (it's the sequel to Little Brother). More books: Rapture of the Nerds (a novel, with Charlie Stross); With a Little Help (short stories); and The Great Big Beautiful Tomorrow (novella and nonfic). I speak all over the place and I tweet and tumble, too.

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http://2012diaries.blogspot.com/ tristan eldritch

The Hard Problem of Consciousness should be in there somewhere.
http://www.youtube.com/user/Freethinkersanon Christopher

I read #45 and thought, hey, we’ve all been there, right? Oh, wait, I meant #35. Really!
http://twitter.com/kpkpkp Kevin Pierce

MUSIC REMIX: “I got 99 problems but my pitch ain’t one.”
http://gadgets.boingboing.net/2009/06/17/music-remix-i-got-99.html
http://twitter.com/chrisjimson chris jimson

It must be a real bitch to have 99 problems.
luddle

Does he not understand that you must make Bowser keep jumping up and landing on the bridge, smashing the blocks beneath him and eventually creating a hole that leads to his certain doom? Still the best Mario game ever, and perhaps an instinctive wish on his part that the game should never be finished.
show me

I don’t see “bitch” in there anywhere. Huh.
- Brainspore
  
  I half expected them to go for a surprise twist revealing that “a bitch” comprises no less than seven of Jay-Z’s problems.
andyhavens

Navel lint is not a problem. It’s a natural resource.
endymion

I doubt #54. World 8, with its rolling tank, super-fast airship, and malevolent sun, was really difficult, maybe the hardest thing we’d ever seen in Mario before. But the final boss of Super Mario Bros 3 was kind of easy. Just get out of the way when he slams down on you.

This is what I call 90% nerd humor– it tries real hard, and gets it almost right… but just not quite. :)
- http://www.ikaink.net Itsumishi
  
  I’ve clocked Mario 2, Mario 3, Super Mario World, Mario 64, Mario Galaxy, Mario Galaxy 2 and a fair few other Mario games over the years. However, ever since I was little every single bloody time I made it to the final Bowser in the original Super Mario Brothers my heart would beat like crazy and I’d just jump right into him.
  
  Perhaps Kanye has a similar problem.
peegee

Chuck Klosterman did it first, and arguably better (way back in 2004!)

http://books.google.com/books?id=Is53I1fXC1YC&lpg=PA6&ots=BetXo-IR54&pg=PA50#v=onepage&q&f=false

What are Jay-Z's 99 problems?

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