A Gallery Of Jay Z's Un-Coolest Moments

Jay Z is an undeniable Hip-Hop legend/industry tastemaker who can’t seem to decide if he’s 24 or 44 which is both sad/hilarious. At some point, he shriveled into the ‘old man in the club‘ who refuses to pass the torch, sit down somewhere and be a stay-at-home dad in 2014.

Hit the jump for Humpback Hov’s un-coolest moments (and remember to check out Moguldom’s “A Genius Leaves The Hood: The Unauthorized Story of Jay Z“ available on itunes NOW).

First, this…

Then…

Remember when Hov said “Can’t wear skinny jeans cause my knots don’t fit” on “Swagga Like Us” or “Timbs, we off that” on “Off That?” Rappers be lyin.

Homeless Hov era.

“Boy from the hood but got White House clearance” — Hov on “Open Letter” before the White House shut it down.