Upstaged By: An almost flawless Eminem

Taking aim at his critics, Jay opens with the quip, “Do you fools listen to music / Or do you just skim through it?” It’s funny, given that the question might be better redirected to himself. How could he possibly have listened to The Blueprint from start to finish and not noticed that its undisputed highlight is Eminem wholesale outshining him? In fairness, Jay does rap well here—it’s just that Em kicks a couple of truly spellbinding verses that hog the spotlight. So much so that while Nas has spouted a lot of nonsense in his post-Illmatic career, even he got it right when he responsibly told Jay, “Eminem murdered you on your own shit.”


Big L, “Da Graveyard” (1995)

Upstaged By: The devil’s son himself, Big L

So there you are enjoying some nice rap music, having a great time listening to Big L and Lord Finesse drop uncouth punchlines, and then suddenly Jay Z turns up on the song and ruins everything for everyone. His verbals on this posse cut are bemusing. First, the boasts are terrible: “When I’m in the zone, better hold your own / ’Cause I like to break when I finish a poem.” Then he does an awkward stutter thing: “Pound for p-p-p-pound the best around / No way you can get up when I get down.” Why, Jay, why? Be specific, please. Then there’s a flurry of tongue-twisty yapping, before the anti-climatic sign-off: “I’m giving these ladies something they can feel ’cause I’m real.” I guess at least we’ve cleared up those prosthetic-dick rumors.

High Potent, “H. P. Gets Busy” (1986)

Upstaged By: The Jaz, and possibly some ruffian neighborhood pals Hov has long since ditched


Jay’ never been shy about his age—well, other than making songs celebrating it while also docking a decade off his birth certificate —so it follows that you can trace his career back to the cusp of hip-hop’s Golden Age. Credited to the crew High Potent, this track rolls with an outdated-by-then production vibe; more interestingly, it kickstarts a 10-year-long series of unsuccessful attempts Hov made to establish himself as a rapper during hip-hop’s most revered and competitive era. Comparing artists from different time periods is always a little futile, but it’s hard to grant Hova G.O.A.T. status when he tried and failed during the days when some of hip-hop’s biggest talents ruled the roost.

M.O.P., “4 Alarm Blaze” (1998)

Upstaged By: The mighty Mash Out Posse

Here you’ve got a great Rocky sample, Billy Danze and Lil’ Fame doing their excellent aggressive shout-rap thing—“You know the M.O.P. status / In the history of crime and rap we’re some of the baddest!”—and their boy Teflon redlining the testosterone levels. This is music you could win the Olympics to, until our pal Hov turns up and flatlines the track. It’s not necessarily a bad verse—it’s just that he’s chosen a needlessly tricksy flow and assumed that smarmy persona of his that’s totally inappropriate given the momentum of the song. Also, let the record show that Jay is the only person in the video who clearly refused to get in the spirit of the soiree and douse himself in fake sweat. Party pooper.


“Big Pimpin’” (1999)

Upstaged by: The distinguished gentleman, Bun B

This is a great listen, even while being one of the most brazenly misogynistic rap songs of all time. Unfortunately, in trying to fit in with the whole double-time Southern-rap shenanigans, Jay screws up his affectations, adding those awkward, asthmatic pauses and doing that whiney thing with his verse. When put up against Bun’s confident flow, it’s easy to separate the man from the boy.


Anything on Watch the Throne (2011)

Upstaged by: That Guy Called West

The Jay/Kanye dynamic is well established by now: A talented but egotistical producer keeps pestering his label boss to let him step up and become a solo artist in his own right, continually gets turned down, but gets his shot and, uh, runs with it. For 2011’s Watch the Throne, it was as if Kanye decided to channel all those prior years of frustration and embark on a mission to lyrically eclipse his fabled big brother. Job done.


“Brooklyn’s Finest” (1996)

Upstaged by: The ghost of Christopher Wallace, past, present, and future.

Snideness to the side, it’s a shame Biggie and Jay never got to record more together, because they clearly had some chemistry. You can argue about who takes the spoils here, though Biggie’s self-deprecating 2Pac quip might just give him the edge. That said, it’s a little hard to listen back to this today knowing how often Jay appropriated Big’s lyrics after the fact. Remember: There are better ways to honor a fallen friend than stealing his work.


“Poppin’ Tags” (2002)

Upstaged by: One-time Guinness World Record holder for the fastest rap, Twista

You know how this goes by now: Jay attempts to keep up with his speed-spitting pals, and while he gets the words out, there are moments when you think he’s about to keel over and ask for an oxygen mask. This time it’s Chi-Town pioneer Twista, Big Boi, and Killer Mike who are in charge of the life-support system.


The Jaz, “The Originators” (1990)

Upstaged by: His musical mentor, the Jaz

Back in the late ’80s, Jay’s benefactor was Brooklyn rapper the Jaz; at the time, the tongue-twisting fast-rap style was all the rage, and Jay happily embraced to the trend. Unfortunately, his contribution to the canon is largely flowing in a style best described as “hot-poker rap”—the rushed verbiage flies from his mouth as if he’s being jabbed with a scalding metal implement. It’s all a little uncomfortable. Also, for some reason, the video here looks like it was aiming for an acid-jazz vibe. (Aside: Prince Paul’s production here is top stuff.)


Big Daddy Kane, “Show & Prove” (1994)

Upstaged by: Eh, take your pick

There’s a whole lot of randomness going on in this DJ Premier-produced 1994 posse cut from Big Daddy Kane’s Daddy’s Home. Along with your venerable host, it also features a former sidekick dancer, a Wu-Tang-affiliated kiddie rapper, one of Jay’s future weed carriers, and hip-hop’s most brilliant ever dearly departed mentalist. For his part, Jay was still putting his faith in his high-strung, tongue-flipping style. Let’s just be glad that eventually he moved on.


“This Can’t Be Life” (2000)

Upstaged by: Everyone’s favorite intelligent gangsta, Scarface

As you dig through Jay Z’s collaborations, you’ll start to notice a trend where he shows the ambition to collaborate with a great guest, but then continually falls short either stylistically or emotionally. Maybe he just gets nervous? Anyway, here it’s Brad Jordan who makes the song cry as he begins his verse by talking about how he got a call on the way to the studio and found out that his friend’s kid had passed away. With hindsight, Hov’s boast that he “flow tight like I was born Jewish” seems a little out of place.


Original Flavor, “Can I Get Open?” (1994)

Upstaged by: Lions, tigers, bears ...

Masterminded by Ski Beatz, this runs with a classic ’94 rugged-yet-funky vibe. Alas, Jay decided to do that impression of a yapping Chihuahua again.


Mic Geronimo, “Time to Build” (1995)

Upstaged by: Amateur canine enthusiast and citrus fan, DMX

More mid-’90s action as Mic Geronimo calls in some favors and assembles a somewhat all-star lineup of Jay, DMX, and Ja Rule, while Irv Gotti plays the producer’s role. Always the good hostess, our boy Jay seems very obsessed with talking about ass-cracks, pressing skirts, and his favorite Moist Deluxe cakes. DMX wins by virtue of a reference to oranges.


“EPMD Freestyle” (1989)

Upstaged by: A sense of decorum

Never let it be said that Jay Z cannot rap while wearing a pink-and-white-striped tracksuit.


Phillip Mlynar lives in Queens, NYC. When not writing about rappers for Red Bull, NYLON, and the Village Voice, he muses on the feline form for Catster. His Twitterclaims he’s the world’s foremost expert on rappers’ cats.

Photo via AP Images.