This is Jay on ESPN's Cuttin' Up (2004) hosted by Jermaine Dupri. I loved this! They talked about sports, what types of books he liked to read, retiring, etc. Jay's knows his sh*t, funny dude too. I think one of the reasons it was good because Jay and JD are cool so it's like a normal conversation btwn the two just with cameras in the room. Good ish!
NOTE: The quality's not that good. I either watched it too many times or I recorded it over something else. It's worth the download though, one of my favorites :)
DL/Watch Jay-Z on Cuttin' Up: