29. MTV Unplugged
When: November 18, 2001
Complex: Real fans remember Jay's MTV Unplugged. The rapper, with the Roots in tow, performed some of his biggest hits, such as "Izzo (H.O.V.A)", "Jigga What, Jigga Who", and "Big Pimpin"—all played in acoustic. It was a great night, which is why his Che Guevara tee (with a long sleeve shirt underneath) will always be remembered.
If you weren't able to see the show, the CD is the next best thing, or this video. Thank you YouTube.