Jay-Z/YMMV

Alternative Character Interpretation: How he presents on of himself on "American Gangster".
Badass Decay
Covered Up: "99 Problems" was originally a rap by Ice-T.
- Within the rock/alternative world, Jay-Z has himself been covered up by Hugo Chakrabongse, who borrowed the same hook for a bluegrass song.
Ear Worm: "I got 99 problems but a bitch ain't one." As well as many of his other songs.
First Installment Wins: His debut Reasonable Doubt is generally considered by critics to be his best album, followed closely by The Blueprint.
Funny Aneurysm Moment: His song "D'Evils" is a fictional account of violent fallout with his friends over Money, Dear Boy. Though no where near as bad as what happened in the song, he did have a falling out with his friend/business partners and some of his artist, resulting in the end of his record label Roc-A-Fella Records.
Heartwarming Moments: His duet with Beyoncé, seen here. It's sweet, charming and cool.
- December 4th from The Black Album is a rather strong one too, as is Empire State of Mind.
- VMAs 2011: Beyoncé reveals her pregnancy after a kick-ass performance of "Love On Top" - cut to Papa Hov and Uncle Ye celebrating in the audience.
Memetic Mutation: "I've got 99 problems, but a bitch is only [some number] of them."
- "If you've got [name of object] problems, I feel bad for you, son: / I've got 99 problems, but [name of object] ain't one."
Moment of Awesome / Take That: After he was slated to headline the Glastonbury music festival, Oasis' Noel Gallagher complained that "Glastonbury has a tradition of guitar music... I'm not having hip hop at Glastonbury. It's wrong." In response, Jay-Z opened his set by walking onstage strumming a guitar and singing a hilariously off-key rendition of "Wonderwall" before launching into "99 Problems". Making this particular Take That especially ironic is the fact that the crowd seized on this as a big sing-along moment, turning a sly, ambiguously hostile retort against Gallagher into a huge crowd-pleasing moment.
- How long did it take him to record The Blueprint? Two weeks. How long did it take him to write all the lyrics? Two days.
- The Takeover.
- His second verse in Blueprint 2
- His other Moment of Awesome with Nas was bringing him at the "I Declare War" concert.
Nightmare Fuel: The "On To The Next One" video, which involves Jay-Z and the director having fun with all the Illuminati-Free Mason rumors leveled against him, and quite a bit of disturbing imagery. Hell, on it's own, the song isn't exactly something you'd want to listen to in the dark.
Sequelitis: Some feel that the two sequels to The Blueprint don't live up to the original. Hell some think that everything he's made up to this point doesn't compare to Reasonable Doubt
Tough Act to Follow: Reasonable Doubt obviously.
They Changed It, Now It Sucks: Some of the reactions to albums such as In My Lifetime, Kingdom Come, and The Blueprint 3 due to them having a more "pop" sound. In some circles the Blueprint get this as well. Or ALL of Jay-Z's output post Reasonable Doubt.