Jay-Z’s Top 25 Deep Cuts: Critic’s Picks


There aren’t that many stones left unturned when talking about a three-decade career that includes 22 Grammys, 14 No. 1 albums, multiple one-liners and slogans embedded in the pop-culture lexicon, numerous decade-end list entries, and a music video shot at the Louvre with Beyoncé. Jay-Z has been getting his roses.  

But if you squint, one of the aspects of Hov’s legend that’s arguably been overlooked is his prolific output. His solo LP discography features 191 songs (not including the bonuses). That number pushes into the half-thousand mark considering features, soundtrack appearances, B-sides, the S. Carter Collection mixtape, collaborations, unfinished leaks, and pre-Reasonable Doubt cuts. With that much material, you’re going to get a “Ghetto Techno” or two. Still, Jay-Z had a high batting average when he was consistently dropping heat during his 1998-2002 prime.

While new Jay-Z comes more slowly these days, the Tidal owner does pop out now and then to show that he still has it. On Friday, he’ll be reopening Webster Hall with another B-Sides concert of rarities and deep cuts, four years after he performed the first edition at Terminal 5. To commemorate, here are some of the best non-single gems to appear on a Jay-Z album.

(Note: All songs from Reasonable Doubt and The Blueprint can only be streamed Tidal.)

"Where I'm From" (1997, In My Lifetime, Vol. 1)

Vol. 1 has been overlooked among his pre-retirement catalog because it’s seen as Jay-Z selling out with Bad Boy-led mainstream trends. That’s a boilerplate way to look at a project when, taken by itself, is really a set of peaks and valleys. One tends to put the pains of the troughs behind them after reaching high ground.

And so you forgive "I Know What Girls Like" and "(Always Be My) Sunshine" once you reach track 13, “Where I’m From,” one of the most vivid depictions of black life under duress ever recorded. Anchored by the brutally economic clangs of Ron Lawrence’s production, Jay-Z effortlessly reifies the memories of the Marcy Houses he survived in. The combination of the two makes “Where I’m From” a physical and claustrophobic experience: The shell casings, police storming out of vans, and pooling blood rushes toward you as Hov delivers the scenes. For the average listener, it’s a harrowing life. For those still living in those houses, it’s the ghetto. For both demographics, cuts like “Where I’m From” prove the question of “Who's the best MC: Biggie, Jay-Z or Nas?” a legitimate one.

"U Don't Know" (2001, The Blueprint)

Vulnerable Jay-Z tends to get a lot of critical praise — note how the warm reception to 4:44 is compared to his other post-retirement albums. But any Jay-Z critic who denies how fun it is to hear him embrace his arrogance is kidding themselves. This is the Hov that’s inviting to live vicariously through, and one of the most thrilling examples is over Just Blaze’s bombastic production on “U Don’t Know.” The Blueprint highlight outright pushes into the absurd. “I am a hustler baby I sell water to a whale,” he brags at one point. But like a true businessman, he sells these lines with unassailable conviction. The percussive way in which he pledges, “I. Will. Not. Lose,” infects you with his pride. This is a hustler’s spiritual.

“Intro/A Million and One Questions/Rhyme No More" (1997, In My Lifetime, Vol. 1

Jay-Z, like many inner-city New Yorkers, is well-versed in the art of minding your business. So, he gets irritated when people try to pry into on who exactly is this guy whose fedora obscures his face on his debut album cover. He wasn’t even supposed to be rapping on a second album, as Jay-Z originally planned for Reasonable Doubt to be a one and done deal.

But now it’s sophomore album time and Jay-Z thumbs his nose at being a star while doing one of the first things he mastered during his early career: rapping over a DJ Premier beat. Over a dulcet Aaliyah sample, he half-playfully dodges the question of if he’s telling the truth about that spot he referred to on Reasonable Doubt “Friend or Foe.” Then Jay-Z goes on the offensive when the beat switches blaxploitation grit. “Motherfuckers can't rhyme no more, 'bout crime no more/'Til I'm no more, 'cause I'm so raw,” Hov announces, kicking off the final part with grim determination. He’s a hustler at his core, but for now, he’s here to rap.

"This Can't Be Life" feat. Beanie Sigel & Scarface (2000, The Dynasty)

The story behind “This Can’t Be Life” has become just as impactful as the song itself. Jay-Z, his engineer Guru, and Scarface were hanging out in Bassline Studios to record “This Can’t Be Life” when the Houston rapper got a phone call saying that his friend’s son died in a fire. Jay offered Scarface a chance to do the verse another time. “Nah, Jig, I’ll do it now,” he said. Scarface, by a small miracle, manages to find clarity in that moment to channel into that into a deeply empathetic verse (“I could've rapped about my hard times on this song/But heaven knows I woulda been wrong”).

The tragedy stands over a rare sight in the first verse: an insecure Jay-Z. Hov has always broken down the dangerous cycles of his former life dealing drugs. This verse finds hustler Jay not believing that his talent as a writer was a way out (“I'm still stretching on the block/Like "Damn, I'ma be a failure"Surrounded by thugs, drugs, and drug paraphernalia”). Even with a close relationship with death, there’s still an audacity in wanting more.

"Never Change" (2001, The Blueprint)

A Kanye West-produced Jay-Z track has the effect of making those 92 bricks feel like a personal loss to us all. Reasonable Doubt and The Blueprint differ in how the former was more so dedicated to the hustlers, while the latter was more accessible to those outside of that life. Still, “Never Change” finds Jay-Z weaving some of the denser street references and nickname shoutouts over West’s wistful David Ruffin samples. But the verses aren’t so labyrinth that the gems do not present themselves. “I'm like a dog: I never speak, but I understand” is a specific street code written sharply enough to be universally relatable.

“Blueprint (Momma Loves Me)” (2001, The Blueprint)

If Reasonable Doubt takes a cold look at the trauma of growing up in the streets, The Blueprint, with all of its highs, argues that suffering has to be for something. The latter’s sobering outro emphatically gestures at that idea. “Blueprint (Momma Loves Me)” is poignant because it’s a reminder that all we’re ultimately our biographies—because Shawn Carter is ultimately human, that’s a fact for him as well. The biographical ending to his most popular classic spends time reminiscing on a community that built him, including Eric, who once fought Jay; Gil who introduced him to the drug game; and Grandma, who fed him banana pudding. The verse-long track’s improvisational elements adds to its sincerity. At one point, Jay interrupts his own rap for a quick aside, because how could he forget to tell his locked-up friend that he’ll take care of his family while he’s away? Jay-Z ends his tribute with a reminder of his mental pen’s nuance: At the very last bar, he switches his repetition of “momma loved me” to present tense. He still carries the streets and its people with him.

"D'Evils" (1996, Reasonable Doubt)

Some of the more significant tragedies of Jay-Z’s stories don’t stop and end with the vile act itself. “D’Evils” lays out that the pains of dirty living eventually poison every aspect of your life. On the second verse, Jay-Z’s narrator exploits the relatively innocent memory of sex ed to point out that a childhood friend never paid attention in those classes. So, he’s here, bribing the mother of his child to reveal where that friend is in order to kill him. DJ Premier’s despondent sample was crafted around the verses’ desolation.

“Jay Z actually called me and recited the whole rhyme on the phone and gave me the concept of what he wanted it to be. So he already knew it was called ‘D’Evils,’” DJ Premier recalled to SPIN. “He told me what the song was about. He did the whole verse on the phone and he even told me which scratches to use. So everything was pretty much already mapped out. He said, “I just need the track to sound like that atmosphere. I just need it to sound like the darkness of the lyrics.”

"Imaginary Player" (1997, In My Lifetime, Vol. 1)

“Imaginary Player” remains one of the clearest examples of Jay-Z’s “conversational” flow that he’s put to record. There’s an ease with which Jay-Z slides that adds a slight shock as he’s putting together those taunts. A brutal intimacy that comes with the delivery of disses like “I got bail money, double-XL money/You got flash now, but time will reveal money” in second-person, shooting the dozens to crumble your life for fun. Barbs like his target not knowing the difference between Cristal and beer stick because the detail feels too specific and mentioned too matter-of-factly not to be true, just like the song’s other flexes. “Imaginary Players” also ends in what’s become a must-answer question for Jay-Z fans hoping to be taken seriously: “What’s the difference between a 4.0 and a 4.6?

"Heart of the City" (2001, The Blueprint)

After pairing up on The Dynasty, The Blueprint found Kanye West and Jay-Z’s dynamic hitting in full stride. “Heart of the City” thrives on this symbiotic relationship. The more money, more problems was already becoming a trope at this point thanks to songs like the Notorious B.I.G.’s “Mo Money Mo Problems,” which Jay-Z namedrops on the track. But West’s sample of Bobby “Blue” Bland’s guitar strums and Jay-Z’s annoyed directness coalesce to make their own aesthetic. The throwback production has the effect of making Hov come across as superheroic. Taunts like “sensitive thugs y’all all need hugs” have grown to become some of Jay’s quoted kiss-offs.

"Come and Get Me" (1999, Vol. 3… Life and Times of S. Carter)

Vol. 3’s penultimate track was inspired by Jay-Z getting frustrated by a visit to his old haunts. People started telling him to be careful as if he didn’t grow up in Bed-Stuy, just because he’s sold a couple of million records. The thing is Jay-Z has been already living expensively. “I been having chains on,” Jay-Z said in a 1999 interview. “I been going through this place since I was a kid…. For people to say that about you around your own way, holmes, you ain’t been scheming on me. You ain’t been doing nothing to me. What makes you think that I sold five million records that you can do something to me?”

The possible assailants included folks outside of his neighborhood: 50 Cent named Jigga in his controversial “How to Rob.” But as Vol. 3 features Jay-Z at his gully-talking peak, “Come and Get Me” represents the man standing powerful and defiant on the album’s cover. Jay-Z notes in the same interview that he knows he’s not the invincible Superman, but that mortality seems to give his lines urgency. The barrage of subliminals (“How dare you look at Jigga like I'm shook like who/I keep the fifth with me nigga, come and get me”) and lethal fighting words (“For niggas that think I spend my days in the sun/Well here's the shock of your life, the Glock not the mic”) lasts for a six-minute thriller whose tension elevates with Timbaland’s production, which evolves from a creeping stomp to sleezy funk tour de force. It turned out “Big Pimpin’” wasn’t a fluke, but perhaps more importantly, after decades of words dedicated to Jay-Z, “Come and Get Me” throws in the most concise explanation of his significance: “I made it so, you could say Marcy and it was all good/I ain't crossover I brought the suburbs to the hood/Made 'em relate to your struggle, told 'em 'bout your hustle/Went on MTV with durags, I made them love you.”

"Streets Is Watching" (1997, In My Lifetime, Vol. 1)

“Streets Is Watching” is the first and last Vol. 1 track Jay-Z was able to show the Notorious B.I.G. before his death in March 1997. Like Biggie’s own “Gimme the Loot,” the track has the distinction of appearing censored even on the album’s explicit version. British musician Labi Siffre purportedly refused to clear the sample of his 1975 song “I Got The” unless the curse words were taken out.  (Siffre’s song popped up on Eminem’s breakthrough single, “My Name Is,” profanity intact.) The technicality doesn’t blunt the speed of Jay-Z’s rapid-fire line leering at surveillance and curious foes. The final verse pushes into a stream of consciousness, evoking a street-learned paranoia in which he fits in an apology to the families affected by his drug dealings. He tosses it in off-beat and moves along, perhaps aware the streets remain the streets even with the mea culpa.

"You Must Love Me" (1997, In My Lifetime, Vol. 1)

Reasonable Doubt and Vol. 1 both end on Jay-Z grappling with remorse even though they’re far from being the same albums. “You Must Love Me” is more or less Hov’s blues record. He’s picking at the scars underneath the Versace, playing it straight in a closer mainly free of his signature one-liners. Each tragedy leads to another. The second verse recounts Jay-Z shooting his brother after an altercation. The violence against his own blood is horrifying enough, but what resonates is that these are young men who know they should do better (“Huffin' and puffin' gun in my hand told you step outside/Hoping you said no but you hurt my pride”). But even though “You Must Love Me” is our wounded hustler taking stock of the surrounding darkness instead of searching for light, it comes anyway. His brother asks to see him in the hospital the next day.

Allure" (2003, The Black Album)

Jay-Z wasn’t above using the gangster movie trope of doing that one last job for his final album. That’s where “Allure” comes in. As the second-to-last track on The Black Album, there’s a nostalgic sheen to on how Jay finds a variety of ways to say he loves the game because he loves the high.

Part of the lifting comes from the plush hums of Pharrell’s production, who refused to let Jay-Z’s final album come and go without landing a beat on it. After making the instrumental, Pharrell excitedly called Hov to announce that he had something that sounded like “the end of Carlito’s Way.” So, Jay raps on “Allure” that he’s in “the starring role in "Hovito's Way." Unlike Al Pacino’s character, Hov lives to unretire.

"Dear Summer" feat. Jay-Z (2005, 534)

“Dear Summer” isn’t the first Roc-A-Fella track to have the featured artist as actually the lone rhymer — Memphis Bleek has the only verse on Vol. 2’s "Intro – Hand It Down." Of course, the big difference was how “Hand It Down” was overshadowed by “Hard Knock Life,” Hov’s biggest single at the time and the album’s very next track. Meanwhile, “Dear Summer” was Memphis Bleek’s last minor hit. The 534 cut’s main story isn’t its odd billing, though: Coming during his retirement years, the track came during a time rap fans had to deal with the fact that a summer’s final sun may set without a new Jay-Z record soundtracking it. Jay reminisces on ruling the season for consecutive years with boastful warmth. With lines like “I drop heat, when you bring the sun up,” “Dear Summer” is watching Kobe Bryant shooting basketball at a gym in 2019, looking to see if he still got it.

"22 Two's" (1996, Reasonable Doubt)

While it seems bizarre in retrospect, there really was a time when not enough people believed in Jay-Z to get him a record deal. Maria Davis, who introduces “22 Two’s,” is one of the few who gave him a chance during those pre-Reasonable Doubt years. The fast-talking personality was known as the host of Mad Wednesdays, a popular weekly party in uptown Manhattan. The event gave Jay-Z a stage when he was trying to get his music and face out to the world. "Well, you know, nobody knew who the hell he was so he was just a regular Joe Shmo to me, he wasn't Jay Z yet," she remembered. "But he was on his way 'cause they had they own label and I was a part of all of that.

Mad Wednesdays featured Jay-Z performing “22 Two’s,” a Davis favorite that eventually became a Jay-Z fan favorite. When he takes the stage after telling him to “put that champagne down, and kick a lil freestyle,” Jay-Z makes it his mission to honor her time with a twenty-two utterances of “two” and its homophones in a verse. While many probably could string this concept together, they’d likely do so as a vein pops in their temple. Jay-Z’s attempt is so loose and fluid, one of his immortal punchlines sounds like it spilled onto the second verse (“At your wake as I peek in, look in your casket/Feelin' sarcastic, "Look at him, still sleepin'"). A signed Jay-Z performed the sequel, “44 Four’s,” at Reasonable Doubt’s 10th anniversary show.

"Squeeze 1st" (2000, The Dynasty)

Although Vol. 3 and The Dynasty are considered his non-classics, the two albums feature some of Jay-Z’s most colorful guntalk. The most potent example from this era is the latter’s penultimate track. “Squeeze 1st” finds Jay-Z sprinting to find every possible way he can vanquish his foes. He’s a focused marksman (“When I greet ya, meet ya with pound/Not the handshake, but the kind that make ya demand a wake”) who cares just enough about the listeners to break the fourth wall to give a blunt advisory (“My scene is vivid/Squeamish kids, y'all get the fuck outta this verse”). He explains away his remorse from his drug-dealing days in half a bar (“I did some things I admit it/Wasn't proud of it, but I was a child, fuck it”). Yes, “Squeeze 1st” structurally centers around another couple of Jay-Z’s many Biggie interpolations, but his charisma makes them feel like ornaments by the track’s end.

The whole thing turns out to be a display of wounded machismo. Jay-Z and Beanie Sigel bitterly rap about how their fathers failed them on the album-closing “Where Have You Been.”

"Murdergram" feat. Ja Rule & DMX (1998, Streets Is Watching)

Jay-Z’s canceled ‘90s supergroups include the Commission (Diddy and the Notorious B.I.G.) and Murder Inc. (Ja Rule and DMX). The former is the more unfortunate miss because, well, it’s Biggie. Still, “Murdergram” is an fierce encapsulation of what could’ve been. It’s a thriller that accelerates off their differing personas: Jay-Z’s cold demeanor (“Cock the hot pistol, then pop the hot pistol/ And promise you only one thing: I will not miss you”), Ja Rule’s raspy wail, and DMX’s horrorcore. Though “Murdergram” is tucked away in the soundtrack for Streets Is Watching—Roc-A-Fella’s urban flick—Murder Inc. would link up with other lineups a few more times before the decade ended, including twice on Vol. 2’s rugged “Money, Cash, Hoes” and flossy “Can I Get A…"

"Bring It On" feat. Big Jaz and Sauce Money (1996, Reasonable Doubt)

If we’re sticking with the rap album-as-mafioso flick theme, then Reasonable Doubt’s “Bring It On” is the scene where the family sits together at the dining table, celebrating their shared wealth and camaraderie. A few were introduced to Jay-Z as Jaz-O’s mentee back in the latter’s 1989 gimmick single, “Hawaiian Sophie.” Here, he’s unquestionably come into his own away from Big Jaz’s shadow, delivering an intricate, coded verse directed at the fellow hustlers he came up with. Though this is Jay’s moment, his man Sauce Money kicks things off with a verse that slickly weaves on and off beat before Jaz-O’s husky presence makes the German word “Fahrvergnügen” more indelible than it was as a Volkswagen slogan. DJ Premier’s production gives this classic cipher its fitting sepia tone.

"Justify My Thug" (2003, The Black Album)

The Black Album’s big surprise collaboration was “99 Problems,” the first major Rick Rubin hip-hop production since the ‘80s. The team-up overshadowed “Justify My Thug” — which brings in underrated West Coast legend DJ Quik — for a number of obvious reasons, but the track does carry its own significance. Coming right after "Public Service Announcement (Interlude)" on the tracklist, the philosophical “Justify My Thug” has more clarity in contrast to his cocksure boasts. The series of mantras (“I tighten my belt 'fore I beg for help”) remains potent even outside of the album’s context.

"This Life Forever" (1999, Black Gangster)

A pre-Reasonable Doubt Jay-Z was riding in his white Lexus 300 through Fort Greene when he saw the ruin outside of his windows — the girls pushing baby strollers, the old women struggling over cracked sidewalks as young men worked the corners. “It f—ed me up,” Jay-Z recalled in Decoded. The title of “This Life Forever” implies a pride-filled pledge similar to Cam’ron’s “Dip-Set Forever.” The actual point is bleaker: The game is not a way to build a life, but to survive. It’s usually inescapable: Jay-Z’s friend died doing the same sort of illicit out-of-state deals he was doing. While double and triple entendres can come across as flamboyant, in Jay-Z’s hands they’re a means to emphasize hard living: “Over my years I've seen rooks get tooken by the knight/Lose they crown by tryna defend a queen.”

Like Ridley Scott’s American Gangster a few years later, Jay-Z found his muse in the unreleased film adaptation of Donald Goines‘ 1972 crime novel, Black Gangster. The consequences Frank Lucas’ faced for drug trafficking and Goines’ grisly end shows the world of “This Life Forever” doesn’t exist in a capsule.

"No Hook" (2007, American Gangster)

Jay-Z’s aggressively fast rhyming on “N—-a What, N—a Who (Originator 99)” is impressive as a physical act. His more prodding, unfolding verses on “No Hook” are just as worthy of praise, as they exemplify precision in his writing and delivery. “Cinematic” has been a sought-after descriptor well before Raekwon dropped his crime film disguised as an album, Only Built 4 Cuban Linx. But Jay-Z’s flow stops, pauses, and climaxes with the vividness and kinetics of a motion picture.The way the smash cuts of dark imagery on the second verse splashes into Jay-Z’s exasperated “choices” strikes like a dramatic wide-shot, jumping from aggrieved mother to an inner-city skyline. Just as essential is Diddy & The Hitmen’s production, which manages to make every instrument tangible. The snares build tension as the bass add a chill to this should-be Oscar nominee.

"Lyrical Exercise" (2001, The Blueprint)

A hidden track, “Lyrical Exercise” coming after the drama of The Blueprint has the feel of a Bucks vs. Warriors preseason game — impressive to witness, yet low stakes. It’s an afterthought when considering the album’s classic status, but this is one of the most instantly quotable songs of his career. Literal exercising as an extended metaphor spins a series of punchlines too sharp and numerous to justify pointing one out over another. “Lyrical Exercise” will remain potent until the gym stops existing as both a physical institution and a concept.

“So Ambitious” feat. Pharrell Williams (2009, The Blueprint 3)

Inspirational Jay-Z shines through even as he’s interpreting other pop sounds. “So Ambitious” is well within the aughties’ post-Graduation futuristic aesthetic, which mainly soared on colorful synths and various twinkling sound effects (compact drums, a use of space). Here, Jay’s riding on The Neptune’s glitzy chords, looking skyward from the earth and rapping about how he rose from poverty. This isn’t a new story, but it’s more memorable than some of the other Horatio Alger-type verses because of its tight construction.The Neptunes’ drums hold their own, but the internal rhyme scheme in Hov’s verses lends the track an extra bounce.

"The Prelude" (2006, Kingdom Come)

Hov’s intros remain essential even during the weak moments in his career (Magna Carta Holy Grail’s title intro track, with its awkward Nirvana reference and weak Justin Timberlake hook, made it to the country’s top 5). Kingdom Come gave us a poor Dr. Dre collab and something about beach chairs, but at least it offered up “The Prelude.” Because this is his post-retirement album, the cliché has it that the intro should sound like a proclamation (see The Blueprint’s “The Ruler’s Back”). But there’s an angular way the lyrics configure themselves with Jay’s intense huff that makes his boasts feel personal. Instead of a royal address, “The Prelude” is an OG grabbing you by the collar.

“The Prelude” has become overlooked not only because of the middling album it’s on: The real king-is-back moment came a month before Kingdom Come’s release when Jay-Z visited Hot 97 for his legendary Grammy Family Freestyle. So, “The Prelude” remains more of a favorite for Jay-Z diehards, including one named Terrence Thornton. The lyrics “n—as beats is bangin', n—a, your hooks did it/Your lyrics didn't — your gangsta look did it” popped up on DAYTONA’s closer, “Infrared.”

“Meet the Parents" (2002, The Blueprint 2)

Jay-Z’s love of movie references also includes borrowing structure. “Meet the Parents” uses Pulp Fiction’s disjointed chronology to weave a bleak street parable: A mourning mother becomes an addict, unable to deal with the grief over losing her son, who was a street hustler who grew up without his father — a man who’d actually be the one to fatally shoot him. “Leaving your son is dooming him” is your moral.

The concept is on-the-nose enough even without Just Blaze’s violins and piano piling on the melodrama. But what elevates the track is the details, which are inspired by Jay-Z’s own experience with fatherlessness. The slain kid hesitates to shoot his killer because he sees himself in his face, not knowing that’s his dad. Clearly Jay-Z’s sympathy lies with him by showing his humanity in this moment. But the ethos of “Meet the Parents” stretches back to 1996: As he laid out in Reasonable Doubt, vulnerability in the streets brings death. It’s weightier because Jay-Z isn’t spinning a fable.

But Jay-Z pointed out in his 2010 memoir Decoded that not everything in “Meet the Parents” holds up. “At the gravesite I introduce the single mother, Isis,” he said. “I gave her an Egyptian goddess’ name because there’s a way we put black mothers on pedestals while at the same time saying they’re incapable of raising boys to men, which I basically say in this song.” Jay-Z becoming Jay-Z proves that isn’t necessarily true.