Uproxx has a new show and in honor of its first guest, New York rap icon Jadakiss, we’re taking a look at some of the mixtape legend’s finest contributions to hip-hop’s ever-grown canon of gritty street classics. In the debut episode of Fresh Pair, hosts Just Blaze and Katty Customs sit down with Kiss to discuss his one-of-a-kind rap legacy, get his top five best rap voices in hip-hop, and show off a unique pair of custom sneakers inspired by his influential 25-year career. From his 1994 debut as a member of The Lox to a successful solo career to his recent star showings on Verzuz, Jadakiss has become one of rap’s most revered figures for his humor, wit, and Yonkers-bred charisma, as well as some of the hardest verses ever to grace a DAT tape. Here are just 20 of his absolute best.
20. “You Make Me Wanna” Feat. Mariah Carey
Over the years, Jadakiss has become best known as a rugged spitter, but he can make songs “for the ladies,” too. As was the custom in his early 2000s heyday, Jada’s R&B collabs proved to be as effective as his battle raps.
19.”Jadakiss Interlude” With DJ Khaled
What better testament to the long shadow Jadakiss casts over the rap world than having his own interlude on DJ Khaled’s God Did in which all he does is rap his ass off, no chorus, no hook, no fancy concept — just bars?
18. “Why” Feat. Anthony Hamilton
Jada’s first — and to date, only — foray into so-called “conscious rap” helped bring down the wall that separated the mainstream from socially aware hip-hop in the early 2000s. Part of the reason is due to the smart framing of “Why.” Rather than preaching at listeners, he invited them into the conversation, simply asking questions — instead of a local organizers’ meeting, “Why” sounds more like a barbershop conversation. Still, even as he wonders at the various shortcomings of society, he finds time to remind listeners why they tuned in to begin with: “Why is Jadakiss as hard as it gets?”
17. “Hot Sauce To Go”
The perfect track to display Jada’s penchant for picking unconventional beats, this Kiss Of Death smooth groover might not be a universal favorite, but it’s hard to deny the salsa flair of its Neptunes-produced beat. Pharrell provides a signature falsetto hook, while Kiss loses his normally gruff demeanor to show he can two-step when it’s time to. While he’s usually mean-mugging and threatening on tracks, this time, he’s ready to party.
16. “Put Ya Hands Up”
Like “We Gonna Make It,” “Put Ya Hands Up” originates from his solo debut album, Kiss Tha Game Goodbye. The third single from the album, it’s a gritty showcase for his head-spinning wordplay, which at the time, was still mind-blowingly novel at the mainstream level. “And y’all scared I can tell,” he boasts. “And I’ma get Bucks like Milwaukee cause like Sam I Can-sell.” In the future, this sort of intricate double entendre would be commonplace, especially on the battle rap circuit, but in 2001, it was like poetry in motion, ahead of its time.
15. “By Your Side”
Although it’s more emotive than some of his earlier material, this standout from Jada’s 2004 album Kiss Of Death still matches with his rugged sensibilities courtesy of a hard-hitting beat by Baby Grand. Weaving a narrative ode to both friends and foes in the streets, Kiss also weaves his flow between the catchy vocal sample, as usual demonstrating that his lyrical talents are up to just about any challenge — even those he imposes on himself.
14. “F*** You” With The Lox
Sidebar: We Are The Streets, The Lox’s 1999 Ruff Ryders debut, has the most hilariously literal album cover of all time. That aside, Jada’s verse here sets things off with a bang as the crew declares the mission statement for the second phase of their careers. “Yo, everybody’s a snake / That’s why I try to keep the grass cut / So I can see ’em when they coming / Then I heat they ass up.”
13. “Knock Yourself Out”
Jada’s debut solo single, produced by The Neptunes, introduced him to the world at large — who until then, only really knew Jadakiss from his features and work with The Lox. Here was his chance to prove that he could offer up more than just fire 16s, one at a time. He passed that test with flying colors with “Knock Yourself Out.” He also, weirdly enough, wore a paper towel wrapped around his head like a bandana in the video, ensuring that rap fans would keep discussing it over twenty years later by memes struggling to decipher that inscrutable decision.
12. “Rite Where U Stand” With Gang Starr
Appearing on Gang Starr’s 2003 album The Ownerz, this track paired Jada with one of his greatest influences and proved he could hang with the pioneers as well as he could his contemporaries. He was also unafraid to use his music to speak on his various industry woes after getting stuck in a less-than-favorable contract with Interscope — another way he blazed a trail for future generations of artists.
11. “New York” With Ja Rule and Fat Joe
In the midst of Ja Rule’s ongoing feud with 50 Cent — which is still going, by the way — the beleaguered Ja released an absolute gem in 2004, recruiting two of New York City’s most respected voices for backup. Unfortunately, it wasn’t enough to save him in the court of public opinion, but “New York” was a blessed byproduct of the battle that remains an example of the power of a collaboration between icons. Also, “I’m in the hood like them little motorcycles” is still one of the greatest things anyone has ever said on a beat.
10. “John Blaze” With Fat Joe, Big Pun & Raekwon
One of a long line of posse cuts on which Jada has stolen the show, his achievement here is made all the more impressive by the lineup. Fat Joe is in full Diggin’ In The Crates mode on this track from 1998’s Don Cartagena, Big Pun packs his verse with dizzying multisyllabic rhyme patterns, Raekwon spits a cool verse, and Nas is Nas. But counting up the quote-ables? Jadakiss goes hard.
9. “Made You Look Remix”
Whatever they were smoking in the studio when they made this should be preserved and distributed to every rapper’s home address weekly. No one would ever drop a dud verse again. Jada came as close as he ever has to living up to his boast that he’s the “top five, dead or alive” with this verse from the remix of Nas’ 2003 megahit.
8. “Blackout” With DMX, Jay-Z & The Lox
An absolute monster of a track, “Blackout” landed on the rap scene like a mortar round. In late 1998, DMX was hot off his smash debut It’s Dark And Hell Is Hot and no one could have anticipated that he’d follow up with another one in Flesh Of My Flesh, Blood Of My Blood. Then, to throw gas on the fire, the Dark Man threw one of the hottest up-and-coming trios in the business on a track with Jay-Z. Naturally, Jadakiss is the match that lights the flame, opening the track with the boast that “n****s throw us on the album, try to boost they sales.” For what it’s worth, it looks like it worked; DMX legendarily became the first rapper to drop two No. 1 albums in the same calendar year.
7. “It’s All About The Benjamins” Feat. Puff Daddy & Lil Kim
Listen, totally aside from the fact that Jada comes in hot with one of the hardest verses on Puff Daddy and the Family’s 1997 album No Way Out, this is actually Jada’s track from the jump by virtue of the fact that he penned Puff’s verse, despite not being totally sure his new boss could pull it off. The rest was history.
6. “Money, Power & Respect” Feat. DMX & Lil Kim
The title track from The Lox’s 1998 debut album, it’s a surprisingly philosophical breakdown of life’s necessities — at least, by The Lox’s standards. I don’t know that they ever read Max Weber’s three-component theory of stratification, but even if they weren’t perusing the sociology section of their local library in their leisure time, they still manage to explain it pretty well to the layman. Jada’s anchor verse sums up exactly why he’s so beloved in the streets: “Nothin’ but the hotness whenever we drop this / Monotonous for y’all to keep hatin’ ’cause y’all never gon’ stop us.”
5. “Gov’t Cheese” Feat. Millyz, Nino Man & DeJ Loaf
A standout from Jada’s most recent album, 2020’s Ignatius, “Gov’t Cheese” depicts an older, wiser Jadakiss getting reflective about all the hard-won knowledge he’s gained from 20+ plus years in the streets and out of them. “Sneakers too tight, you had to wear ’em without soles,” he reminisces. “Sleepin’ with a sweatsuit on ’cause the house cold.” He doesn’t just bring problems, though; he also explains his solutions. “Had to open my mind for me to free it.”
4. “24 Hrs To Live” With Mase, The Lox, Black Rob & DMX
Mase’s 1997 Bad Boy Records debut Harlem World is criminally underrated and this posse cut is one of its highest highs. Asking a simple question, we get six different perspectives ranging from relatable (Jada, Styles) to absolutely unhinged (DMX). Who among us wouldn’t want to go out as fresh as Jada says he would?
3. “Time’s Up” Feat. Nate Dogg
The lead single from Kiss Of Death finds the Yonkers native eschewing clever concepts or heady themes for a straightforward, fist-clenching bar fest. Driven by a thundering, piano-centered loop devised by Scott Storch, “Time’s Up” is a showcase for some of Jada’s most memorable punchlines, including the fan-favorite: “F*ck riding the beat, n**** / I parallel park on the track.”
2. “Who Shot Ya Freestyle”
When The Lox went up against The Diplomats in a Verzuz hits battle last year, the Yonkers crew had already won handily by the time their DJ threw the instrumental to The Notorious B.I.G.’s controversial 1994 hit. Jada’s performance became the victory cigar. The response to the mixtape favorite was so immediate and powerful, the song won an official release on DSPs.
1. “We Gonna Make It” Feat. Styles P
A classic in every sense of the word, “We Gonna Make It” begins with one of the most beloved opening lines in hip-hop: “F*ck. The. Frail sh*t.” The Alchemist pulls out all the stops on the beat, which samples “My Music” by Samuel Jonathan Johnson. The instrumental has a controversial backstory as well, ending up in the hands of West Coast rapper Ras Kass after both Nas and Jay-Z passed on it, but Kiss has the most recognizable version, owing a great deal to the dynamic back-and-forth flows of Jada and his Lox bandmate Styles P. It wasn’t the first time they demonstrated this chemistry and it wasn’t the last, but for a generation of rap fans, it’s easily the best.