*-A completely subjective list.

What can be said about Jay-Z that hasn’t already been said? Hell, what can be said about Jay-Z that he hasn’t himself said? In the 21 years since he dropped his debut, Reasonable Doubt, the man born Shawn Carter has transformed hip-hop. Who knew that the sidekick in Jaz’s novelty single/video “Hawaiian Sophie” (think DJ Jazzy Jeff & The Fresh Prince) would go on to become a legend with more chart-topping albums than any artist in history other than The Beatles?

Jay has lasted this long by using some savvy business skills, aligning himself with the right artists at the right time (from Biggie & Puffy to DMX & Ja Rule to Michael Fucking Jackson to his discoveries Rihanna, Kanye and Ne-Yo to Justin Timberlake and Beyonce). His music has been…inconsistent. While Jay certainly has a list of certified bangers (see below), his albums can often be frustrating affairs in which the rapper appears to be phoning it in. I actually think he did that more at the beginning of his career, although I’m not sure if I hold Hard Knock Life in less exalted opinion than I hold The Blueprint, The Black Album and American Gangster because it’s not as good an album or because I was beaten over the head with it working in retail during 1998-1999.

Nah…it’s not as good.

Anyhow, here are my favorites from Jay’s lengthy catalog, including his guest spots on other artists’ records. Select titles of his aren’t available via Spotify (including his debut, Reasonable Doubt), so excuse the holes in the playlist.

1) 99 Problems (from The Black Album, 2003)
2) Lucifer (from The Black Album)
3) Interlude: Public Service Announcement (from The Black Album)
The Blueprint, released in 2001, was Jay’s most consistent album-length statement. 2003’s Black Album had lower lows (the less said about “Justify My Thug”, the better), but featured some of his sharpest rhyming. It also featured a series of big-name hip hop producers offering up their best beats. In the case of “99 Problems”, Rick Rubin delivers a speaker-obliterating mixture of rock guitars and Bonham-esque drums. Kanye’s “Lucifer” offers up an intentionally muddy reggae beat, and Just Blaze’s “PSA” (which is a full song, fuck all the interlude bullshit) rolls out with a triumphant swagger. This is to say nothing of the lyrical content. While “PSA” offers fairly typical ego-driven grandstanding, the first two songs contain some of Jay’s sharpest storytelling.
4) Diamonds From Sierra Leone (remix) (from Late Registration, 2005)*
Kanye’s not a rhyming god by any stretch of the imagination (thank Jeebus he’s a fantastic producer and is at least witty), but featuring a completely-on-top-of-his-game Jay-Z on a remix of Late Registration‘s lead single almost rendered ‘Ye useless on his own song. Stung by criticism that the Roc-a-Fella brand was falling apart, Jay delivers one of the hungriest verses of his career, highlighted by the immortal line “I’m not a businessman, I’m a business, man!” Slow down, Hov, you’re killin’ em.
5) Crazy In Love (from Dangerously In Love, 2003)**
6) No Church In The Wild (from Watch The Throne, 2011)*
Not gonna lie…Jay is probably the least interesting part of “No Church In The Wild”. But you can’t front on this song at all.
7) What More Can I Say? (from The Black Album)
One reason (of many) that I began to hate Busta Rhymes: according to a Vibe article, Bus-a-Bus got heated when he heard Jay call him “animated” on “What More Can I Say”‘s third verse and decided to go after him in song. Bruh, go to dictionary.com. He wasn’t dissing you.
My favorite moment of “What More Can I Say”: Jay spends the entire song warning folks that they’ll miss him when he’s gone (The Black Album was supposed to be the last record he made before retirement), then ends the song by saying “fuck this” and dropping his microphone (which I’m pretty he stole from Big Daddy Kane, but whatever.)
8) U Don’t Know (remix) (from Blueprint 2: The Gift & The Curse, 2002)***
9) Brooklyn’s Finest (from Reasonable Doubt, 1996)****
Three songs that perfectly capture pre-gentrification Brooklyn. You can almost see the Army jackets, smell the weed, and get the sinking feeling that you’re about to get robbed during his collaborations with Biggie and M.O.P.
10) Otis (from Watch The Throne)*
The two biggest hip-hop stars at the time release their first album-length collaboration (thankfully way better than Jay’s teamings with R. Kelly and Linkin Park), and the lead single has no chorus. Ballsy as hell.
11) Ignorant Shit (from American Gangster, 2007)*****
12) Heart Of The City (Ain’t No Love) (from The Blueprint, 2001)
13) Takeover (from The Blueprint)
So, who really won the Nas/Jay battle? Let’s look at things like intelligent adults. “Takeover” was a methodical, truthful dressing down while “Ether” was emotional, based on schoolyard taunts, half-truths and gay-baiting. If this was a real-life non-rapped argument, who would win? Exactly.
14) Song Cry (from The Blueprint)
15) 22 Twos (from Reasonable Doubt)
A reminder that even though Jay’s ethos prioritized money over skills, dude was insanely talented on the lyrical tip. It’s amazing how he went from blatantly ripping off DAS-EFX (see Bi Daddy Kane’s “Show & Prove” from ’94) to putting on a rhyme clinic on this “live” recording.
16) Meet The Parents (from Blueprint 2)
The best lyrical narrative of Jay’s career. “99 Problems” gets the nod because of the production (and the fact that Jay decided to write a hook for that one…well, he borrowed the hook from Ice-T, but you get what I’m saying…)
17) American Gangster (from American Gangster)
18) A Million And One Questions/Rhyme No More (from Vol. 2: In My Lifetime, 1997)
19) Roc Boys (And The Winner Is…) (from American Gangster)
20) Streets Is Watching (from Vol. 1: In My Lifetime, 1997)
21) Izzo (Hova) (from The Blueprint)
22) Who U Wit (from the Original Soundtrack Sprung, 1997)
23) Dead Presidents (from Reasonable Doubt)
“You made it a hot line/I made it a hot song”? Not exactly, because “The World is Yours” is a banger. But I get the sentiment, Jay.
24) I Just Wanna Love U (Give It To Me) (from The Dynasty…Roc La Familia, 2000)
Probably docked a few spots due to radio saturation, but it’s worth remembering that “I Just Wanna Love U” (along with Mystikal’s “Shake Ya Ass”, released just a couple of weeks earlier) are the two songs that made The Neptunes THE NEPTUNES.
25) Kingdom Come (from Kingdom Come, 2006)
Lost somewhere in the muck that was Jay-Z’s rusty 2006 “comeback” album was this Just Blaze-produced gem. While Jigga unleashes flashes of his sharp pen game here, the show is stolen by Blaze’s masterful flip of Rick James’ user-familiar classic “Super Freak”.

1-Jay Z featuring Kanye West (“No Church” gives additional featured credit to Frank Ocean and The-Dream; “Otis” gives additional featured credit to Otis Redding.)
2-Beyonce featuring Jay-Z
3-Jay-Z featuring M.O.P.
4-Jay-Z featuring The Notorious B.I.G.
5-Jay-Z featuring Beanie Sigel
6-Jay-Z featuring Foxy Brown