The 50 Best Cash Money Songs

In the history of hip-hop, no label has had the success of Cash Money. The baby of Slim and Baby remains the most successful empire in rap music, more than two decades after its humble beginnings with a 15-year-old rapper named Kilo G. Through multiple generations, Cash Money has defined the sound of popular hip-hop, transcending our greatest icons, producing lasting stars that defied the critics and transformed the shape of the genre. No less a figure than Def Jam founder Russell Simmons recently penned an editorial arguing the label was the best company in rap history.

Of course, not everyone under the label's thumb has been happy with their treatment. As much as Baby and Slim deserve credit, the first half of the company's history depended entirely on the genius of Mannie Fresh for its success. Nonetheless, the label has persevered even without him. From its early days as an innovator creating gangster rap in a bounce city, to the arrival of the Hot Boyz and the Big Tymers of Cash Money's golden age; from the landmark deal with Universal that forced major labels to deal on the artists' terms, to the rise of Lil Wayne as not just the genre's greatest talent but its most popular one as well; from "A Milli" to the emergence of Drake, Nicki Minaj, and Young Money as superstars in an era where almost every other rapper struggles to breach the Top 40, YMCMB has sustained.

And this is to say nothing of the label's talent outside of hip-hop, where teen pop stars like Austin Mahone, R&B talent PJ Morton, and soul music legend Teena Marie found traction. OK, so it remains to be seen what Cash Money can do with Limp Bizkit's career in the twenty-teens, but suffice it to say that the label's impact has been even wider than this list could cover.

Still, when it comes to Cash Money's bread-and-butter—rap music—it's tough to top the diversity and depth of these records. Without further ado, here are the 50 Best Cash Money Records Songs.

Written by David Drake (@somanyshrimp)

Album: We Are Young Money

Producer: Tha Bizness

An ambitious goal even for Lil Wayne, “Every Girl”'s message resonated because a lot of people have had very similar thoughts, and articulating the obvious, unspoken truth is something rap music is very good for. An important peg of post-Carter III Wayne's push for Young Money, We Are Young Money really only propelled Drake and Nicki—Gudda Gudda never quite took it to the next level. Outside of that, the '09 Young Money output was about a focus on rap music's most juvenile roots, its id writ large.

Album: Project English

Producer: Mannie Fresh

Project English didn't measure up to Tha G-Code, never mind 400 Degreez, and after its release Juvenile would temporarily depart Cash Money Records. The label's late-'90s era was quickly coming to an end. But the record was still worth a few singles, especially “Mamma Got Ass,” which is basically the thinking man’s “Back That Azz Up” as it explores human genetics to great depth: “Damn that girl sexy, her mamma got ass too!” Also, not the most important detail per se, but check out pre-fame Cash Money street teamer Paul Wall in braids at around :38 seconds in the video.

Album: Chopper City

Producer: Mannie Fresh

B.G.'s morbidity was his purpose and an eerily relaxed menace was his primary weapon. There was no aggression or anger in his voice, only in his lyrics, and even those words seemed more disappointed by your true character (“You's a ho, so stay on your side of the field”) than offended. His vocals have an unsettling calm, the grain-flecked timbre of his vocal cords one of the most distinct sounds in rap history. Mannie Fresh, cheeky as ever, references the music from The Good, the Bad, and the Ugly to call on the history of the Western shoot-em-up. The picture in question in the song's title, naturally, is the picture that'll appear on T-shirts after you've been killed.

Album: Get It How U Live!

Producer: Mannie Fresh

Before the Hot Boys took off nationally, the Mannie Fresh-produced Get It How U Live sold 75,000 records independently. Although this was a respectable number for independents, it was an inauspicious announcement for such a major musical force. Soon, Cash Money would have a major distribution deal with Universal, and the group would have gotten it where they lived. “Neighborhood Superstar” established the archetype of their success: “Feared by many and loved by broads.” Accompanied by the Big Tymers, the record's gentle, lilting sound would be pulverized by later singles that stepped up the energy considerably.

Album: Pink Friday: Roman Reloaded

Producer: Kenoe

Nicki Minaj's career is frequently spoken of as being a continual conflict between hip-hop and pop, as she's struggled gamely to manage the widening gulf between hit rap singles and hit pop (EDM) songs. Even artists like French Montana seem adept at pulling out a street single when they need to; for the most part, Minaj grapples with making hip-hop records that maintain some level of hit capability. The one exception to this rule is “Beez in the Trap.” Produced by Kenoe, a beatmaker who had started out with No Limit Records, the song's simple, stripped-down formula and tremendously catchy hook transformed the single into one of Minaj's strongest rap singles. A guest verse from 2 Chainz at his creative peak certainly didn't hurt either.

Album: Monkey on the D$ck

Producer: Mannie Fresh

A bounce classic, “Monkey on tha Dick” is probably—and unfairly—more known today for its cover art than its music. But Magnolia Shorty's song sustains, its charms unaffected by the passage of time. Slipping right in between the twin poles of effortless amateurism and rehearsed technique, the song sounds at once tossed off and impossible to imitate. Mannie Fresh's beat, meanwhile, has a sparkling atmosphere reminiscent of Detroit techno as much as rap music, while the drums could come from nowhere but New Orleans.

Along with Ms. Tee, Magnolia Shorty was one of the first female rappers signed to Cash Money, and Monkey on tha D$ck would be the label's last pure bounce record. Tragically, Magnolia Shorty—who got her name from fellow Magnolia projects rapper Soulja Slim—was murdered in 2010 at the far too young age of 28.

Album: Juve the Great

Producer: Mannie Fresh

Juvenile's Project English was underwhelming creatively and commercially. After the multi-platinum 400 Degreez and platinum Tha G-Code, it only went gold, which in those days was a definite sign of waning relevance. Soon after, he fell out with Baby and Slim. But he soon—if only briefly—returned, and Juve the Great was a real comeback: his rap style had a more mature edge, his vocals deepening. Mannie Fresh was no longer the album's only producer. And of course “Slow Motion” became a No. 1 hit record, helping shift the album to platinum status.

“Bounce Back” was the record's third single, a Mannie Fresh-produced, Cameo-sampling, sunny day pop song. The song feels like the album's spirit, as well as a reference to Juvenile's origins as a bounce artist. The song's bright mood seems to push his lyrics into clearheaded optimism: “Try to be here to see my seeds, when they have they seeds/As long as I breathe, there ain't nothing in this world that they can't be.”

Album: Lights Out

Producer: Mannie Fresh

Before he became a true solo star, “Shine” was Lil Wayne's peak pop moment. With a sunbeam of a beat from Mannie, the song's earnest giddiness was so bright as to be blinding. The beat has the elastic bounce of a tiny rubber ball, and its effusive catchiness has virtually no competition in the Cash Money catalog. It's a celebration of the good life and proof of Mannie's pure pop brilliance.

Lil Wayne is also on the song, of course, as is West Coast gangster Mack 10. And it's not like there aren't quotable lines in abundance, from Wayne's “All these carats like I'm a fuckin' vegetarian” to Mikkey Halsted's “The ice is blue, the Remy is red, haters turn green, queens wanna give me some head” (see the video version). But at the end of the day, it's the hook and beat that make this record a classic, a Mannie assembly line record more powerful than Prozac.

Album: Chopper City

Producer: Mannie Fresh

Chopper City was the record where Lil Doogie became B.G., thanks in part to the audience's misconception about who exactly “The B.G.'z” were; with Wayne recovering from accidentally shooting himself in the chest, the follow up to the duo's debut was Lil Doogie-heavy, and so B.G. was born.

Compared with the uptempo dash common to later Hot Boyz records, “Retaliation” was a mid-tempo record that found B.G. in a more writerly mode, rather than relying on his typically creaking vocal style: “You sleep six feet I tear down the whole street/Wear down the family they grieve because ya flat/Bust ya head up leave ya deader, yo blood redder.” Early Cash Money R&B singer Ms. Tee takes the chorus, and Juvenile opens the record, but it's Bun B who steals the show to bring the record to a close: “A dead ass nigga can't talk, wave or blink back/Click! Snapshot, to me your rap's not/That hot like a fat rock off a crack spot.”

Album: Bounce Slide Ride

Producer: Mannie Fresh

Although early Cash Money artists aren't well known by the genre's mainstream, hip-hop today would not be the same without Lil Slim. It's worth reading his full, well-researched biography on Amoeba's website for details; Lil Slim not only discovered Lil Wayne and introduced him to Cash Money when the junior rapper was only 11 years old, but was largely responsible for Wayne's early style. Lil Slim's early recording career was influential, and although he would leave Cash Money because he claimed (believably) that the label owed him money, eventually relocating to Northern California, his legacy remains. “Bounce Slide Ride” from his bounce-oriented debut, The Game Is Cold, flips the “Triggerman” break that operated as the genre's foundation. It added a sample of Earth, Wind and Fire's “Beijo.”

Album: It's All on U Vol. 1

Producer: Mannie Fresh

While B.G. is generally remembered as the grim and gritty street soldier who rapped about murder with a dirt-flecked, heroin-addled, lethargic drawl, sometimes he rolled out of bed on the right side and enjoyed life's finer things. (Don't forget: Despite his grungy reputation, his was the name on the emblematic “Bling Bling.“) “Get Your Shine On” was such a successful concept, it would be cannibalized by future generations of Cash Money songwriters, never mind Florida Georgia Line singles. But the best of all these releases was first: B.G. and Big Tymers' collaboration “Get Your Shine On” sparkled.

B.G. celebrates with a different car for each day of the week and an Uzi under his seat. Baby, meanwhile, differentiates himself from the rest of rap while advertising his billing rates: “I ain't no rapper, I'm a game spitter/Ten Gs a show, that's the only way you gonna see Baby at a concert, you know.” He also claims to have a million dollars buried under a barbershop from selling kilos, which he was doing in his free time after running a record label. Stranger things have happened. Mannie goes for a humorous angle, fucking “more bitches than the sea got fishes.”

Album: Tha Block Is Hot

Producer: Mannie Fresh

Hollygrove native Lil Wayne wasn't remotely a household name when his debut album was released in 1999. At that point, Cash Money had established itself as a force to be reckoned with; they'd had numerous Billboard smashes since Juvenile's 400 Degreez emerged the previous year. It was, no doubt, part of why B.G. and Juvenile—at that point, much, much bigger stars than Wayne—appeared on the record's chorus.

Wayne's verses at this point were solid if a bit pro forma; there are some moments of solid imagery, such as when Wayne ducks the cops into Ms. Taylor's yard and has to hide because she's on the porch. Mannie Fresh's production is distinct as ever and elevates the material around it. Wayne's vocals have the scratchy texture of B.G. and bounce with a sloppier rhythmic sense than Juvenile. Anyone who says they foresaw his future is a liar. But at this point, his career was in its nascent stages. His narratives had a kinetic energy, the feeling of non-stop actions causing reactions. There was no time for punchlines or cerebral reflection; it was all a blur of jump cuts.

Album: The Bloody City

Producer: Mannie Fresh

Kilo G was the first Cash Money artist, signed to the label when he was only 15 years old. While most of the city had been overtaken by bounce music, Kilo G's style was more reflective of the more shocking street rap style of acts like the Geto Boys. While his debut didn't do too much damage locally, his follow-up, The Bloody City, added an essential ingredient to the mix: Mannie Fresh. With Fresh behind the boards, Kilo G's second album was one of the most successful in Cash Money at that point.

Released in 1995 with guest spots from Cash Money rappers like Tec-9 and Lil Slim, as well as a couple of rising stars named Pimp C and Bun B, it became a New Orleans gangster rap classic. The harrowing title track, which closes out the album and features a spazzing Mr. Ivan and future No Limit signee Skull Duggary, is one of the album's more blistering cuts, but the entire release is worth seeking out. Sadly, two years later, Kilo G was gunned down outside of his house in New Orleans' 7th Ward.

Album: Juve the Great

Producer: Mannie Fresh

Juvenile went from being one of rap music's biggest stars to leaving his label after 2001's Project English. Along with his UTP crew, he stuck to underground releases before reuniting with Baby and Mannie for 2003's strong comeback record Juve the Great. Lead single “In My Life” was a minor hit—certainly in comparison to its No. 1 smash follow-up—but at the time, felt like a refreshing approach. Mannie's new sound (and new introductory patter) drained some of the glimmer from the late-'90s excess, relying on a grimmer, menacing flavor. Juvenile, meanwhile, seemed to deepen and center his voice, rounding out his words and letting his drawl sink into each syllable. The strongest facet of the record, though, is its chorus, in which Mannie's boasts trade off with Juvenile's commands.

Album: Chopper City in the Ghetto

Producer: Mannie Fresh

The Hot Boyz's music was often at its best at its most propulsive, each rapper darting across the beat with brutal inevitability. B.G.'s Chopper City in the Ghetto, one of the most consistent records in the Hot Boyz canon, was a collage of action snapshots. And “Niggaz in Trouble” was one of the album's best collisions of music and message, a beat so fast its vocals layered as if the record's momentum were moving out from underneath it. The beat jumps from distorted bass to sudden slamming orchestra hits to panting breath over drums.

Although early Wayne is often disparaged, his bars here, spit in short bursts, are often clever (“When I creep through the black in the black-on-black”). Juvenile's verse jumps to different narrative positions, from first person to a neighbor calling the cops to an older gangster dishing advice: “But remember this, you started this, so finish this/When you grab your shit better make sure that you hit.” Up against tough competition in a song singularly focused on murder, it's B.G. whose verse is the most viscerally unnerving, promising to duct tape his victim and throw acid and gasoline on his face before ending with the ultimate disrespect: “Cut his tongue out and stamp it, mail it to his mom.”

Album: Pink Friday

Producer: Kane Beatz

“Super Bass” remains Nicki Minaj's peak popular moment, an undeniable chart-topping monster that united the euphoric Esther Dean melodies of contemporary pop music with her own undeniably sui generis rap style. Propelled by Kane Beatz production, Nicki's verses don't just clash with the hook's submissive euphoria; rather, Nicki is running an internal monologue about her own uncontrollable attraction, in complete control of the process. She's objectifying one minute, and caught up in attraction the next—likely a lot more real for both men and women than songs that cultivate one or the other approach exclusively. But of course, the hook does a lot of heavy lifting too, with that arching melody reminiscent of Katy Perry's equally dominant “Teenage Dream.”

Album: Tha Carter II

Producer: T-Mix

At this point in his career, Wayne was making strides with East Coast rap fans who'd previously written him off. Well, in all reality he was making strides with everyone—but records like “Hustler Musik,” in retrospect, have a particularly targeted appeal. Although the song is produced by T-Mix, one of the most important talents of the Suave House era, the beat is of a piece with other soul-signifying records of the post-Kanye West era, like Jeezy's “Go Crazy." At this point, it was Wayne's particular delivery, rather than his wordplay or eccentricities, that stood out.

Album: How You Luv That Vol. 2

Producer: Mannie Fresh

Balling was a lot more than a hobby to Cash Money Records, which was on the verge of taking over the rap game when the Big Tymers' definitive rap record was released. Packed with quotable lyrics and riding a bouncing synthesized horn line, “Big Ballin'” captures the duo's effortless humor and panache, and even argues they've been underrated.

In many ways, the record is an old school throwback: not only does Mannie paraphrase Run-DMC’s “Sucker MCs,” but the two trade verses like an old routine, spit origin stories, and shout out friends from the neighborhood.

Quotables abound, with Baby rapping believably about being fronted kilos before slipping into a “Broken Language” type flow: “Titty-watcher, ho-stopper, VCR tape popper, neighborhood naked flick watcher.” The quote that stands out the most now—knowing how things turned out—has to be this prophetic gem from Baby: “And Cash Money Records gonna run the nation with these hits, and playa, you can believe that shit.”

Album: Baller Blockin'

Producer: Mannie Fresh

At times, Mannie Fresh could be one of hip-hop's most whimsical producers, with range and versatility in his heyday that rivaled the genre's greatest beatmakers. Never was that more clear than on the ludicrous “Project Bitch,” which rode bubble sound effects, tiny pizzicato string plucks, and of course one direct, unforgettable synth-horn riff into our eardrums for eternity. The Hot Boys and Baby were never the most strident students of etiquette, but Mannie knew that the right canvas for that kind of bawdy irreverence was undeniable catchiness mixed with a strong dose of absurdity.

Album: Careless World: Rise of the Last King

Producer: DJ Mustard

Think back, if you can, to 2010: DJ Mustard was an unknown beatmaker grinding it out for YG in Los Angeles. The biggest hip-hop anthem—in presence, if not sales—was Rick Ross' titanic “B.M.F.” That and Waka Flocka's Flockaveli radically shifted how popular hip-hop would sound for the next two-plus years. Also released that year was “Rack City,” a beat intended for YG but thrown to Tyga as a mixtape cut. Eventually it would be upgraded to the lead single for the rapper's Careless World: Rise of the Last King album, hit the top 10 of the Hot 100, launch Mustard's career and prepare the world for the producer's pop chart takeover. It was, like most Tyga singles, a dry, emotionless record, but also unforgettable, with a three-note bassline and textural stickiness that sat completely apart from everything on the charts…well, except “The Motto.”

Album: Priceless

Producer: Drumma Boy

For being one of Southern hip-hop's most prolific and important producers, Drumma Boy did not do much chart damage with his singles on the Hot 100, even if they perform exceedingly well in hip-hop channels. One major exception was Birdman's “Money to Blow,” further evidence that Drake's recent chart success was no fluke. Although Drake's sung verse now sounds vaguely silly with its mid-period Drake-isms (the Rufio reference…), his chorus was simply undeniable, particularly when his voice fluttered through the word “Blaa-ha-hoo-hooow.” Wayne's words were prophetic: “We popping like champagne bottles but we never shook/And we gone be all right if we put Drake on every hook.”

Album: Tha Carter II

Producer: Bigg D

Although few will admit to it today, the notion that Lil Wayne was the “Best Rapper Alive” when 2005's Tha Carter II was released was not taken very seriously by your usual hip-hop figureheads.

Of course, it's easy to age out of what's happening on the ground in hip-hop, but to those who were paying attention to the genre's rapidly shifting terrain, Wayne's claim seemed audacious but suddenly within the realm of possibility. Jay Z was retired—at least temporarily. Kanye West was a great artist but not taken particularly seriously as a rap-qua-rap talent. Few people had a lock on the streets and the clubs the way Wayne did.

Of course, one thing he was missing was that pop crossover moment, that “Hard Knock Life” record that would propel him from hip-hop's biggest name to a true superstar, and he wouldn't deliver it for three years, on this album's sequel. But the guitar-scarred “Best Rapper Alive” is what opened the door. It didn't matter if you thought it was true or not; Wayne laid the debate on the table, and now he just had to deliver.

Album: So Far Gone

Producer: Boi-1da

For some people, “Best I Ever Had” was an introduction to a brand-new artist, a former TV star who was now clearly capable of producing huge hit songs. For others, there was a tinge of disappointment, because now it seemed obvious: Drake really was going to be a star, and there was nothing you could do about it. The one thing both audiences wouldn't deny? That the record was an undeniably catchy record, silky-smooth and replete with a sing-song chorus. It was so good, even the tackiness of its video—which in retrospect was one of the most “Drake” things about it—couldn't hold it down.

Album: Guerilla Warfare

Producer: Mannie Fresh

A four-part cautionary tale about evading the Feds, “Tuesday & Thursday” was a highlight of the Hot Boys' Guerilla Warfare. It's a straightforward conceptual record—two days a week the law is on the lookout, so steer clear, told in a chorus of four. It's Juvenile's verse that stands out the most on this record; the way he phrases certain ideas (e.g., “My pride don't want me to be up in this place/My pride don't want the law to notice my face”), compressing complex notions into a small space. “Who do you think be pushing them birds up in the hood?/Who do you think be dumping them bodies up in the wood?”

Album: Nothing Was the Same

Producer: Mike Zombie, Noah “40” Shebib

Drake's style has increasingly favored stripping down his approach to its basic elements, removing unnecessary decoration, and “Started From the Bottom” was a perfect example of the sparse directness to come. Sounding at once tossed off and pristine, the record's crystal-clear sound relies on a simple piano line and unforgettable drum groove. Lyrically, Drake's approach was smart. Instead of running from criticism, he embraced it, owned it. Whether or not he recognized or appreciated hip-hop's class struggle isn't nearly as relevant as his realization of their resonance. But that's exactly why it worked: whether an active troll, complete denial, or a sincere message, Drake found a home in his own contradictions.

Album: Solja Rags

Producer: Mannie Fresh

“That was the song that set it off,” Juvenile told Complex two years ago, discussing how his second album sold 200,000 copies and helped set the table for the label's landmark Universal deal. “That’s what gave me the idea to start making records like that. Just rhyming in patterns that’s different and odd. The first time you might not like it, but if you listen to it two or three times it’ll get ya.” “Solja Rag” sounds today like a proto-“Ha” joint, from its second-person POV to those unexpected flows to, well, some of the same lyrics. Underrated is Mannie's beat, which sounds like the last gasp of a patient in the ER as parade whistles ring out.

Album: Young Money: Rise of an Empire

Producer: Detail

Proving yet again that Hot Stylz are one of the most underrated influences of the past decade, Nicki Minaj's “Looking Ass” was as much a cultural movement as it was a song, an assertion of Minaj's Seriousness, packed with loaded imagery and skirting controversy with unapologetic aggression. Although its Malcolm X cover art and the huge guns she hoists in the video drew fire at the time, she was protected by her move to a more masculine pose. Gone were the bright colors and funny voices. In its place was precision, focus, and earnest grit.

Album: Guerilla Warfare

Producer: Mannie Fresh

What kind of boys record a record trading off every two bars in the late 1990s? What kind of boys take advice from Mannie Fresh to replicate old school routines on their records in order to sell a hip-hop boy band? What type of boys blended that formula with reality rap, filming a music video where they're on the run from the police? What kind of boys released a classic single on a classic album that inspired a gimmicky blurb at Complex?

Album: Like Father, Like Son

Producer: Jim Jonsin

Presaging years of Lil Wayne nursing the electric guitar, “Leather So Soft” complements its title with a soft rock etude that could easily double as a Crosby, Stills & Nash backing track. Only with Lil Wayne rapping about how his rag is as red as period blood, and Baby opening his verse with the inexplicable, “She soft as a bush, nigga/She purple like kush, nigga.” It's an odd record, relaxed and funky in the way Boz Scaggs can be, and the radio edits censors at least 40% of Baby's verse, but it's still got an insouciant charm and some bars from Wayne that seem smarter once you think about them: “You see the paper gonna come, if not I'm gonna get it/I gotta die with money 'cause I wasn't born with it.”

Album: Guerilla Warfare

Producer: Mannie Fresh

Despite the bawdiness and brutality of certain Cash Money tracks, the Hot Boyz and the Big Tymers' songs “for the ladies” were as crucial to their catalog as the more gangster-oriented singles, and showed less contempt for female listeners than many other hip-hop artists at the time. Opening with a series of 808s claps, Mannie flipped the script with an unlikely lunge for the pop jugular: synthesized harpsichords and a timeless melody that proved—yet again—the medium of bounce was something that would easily translate into the American mainstream.

Album: Fast Money

Producer: Batman

One year after the release of Lil Wayne's breakout Tha Carter, Baby—now officially re-christened Birdman—dropped Fast Money, his third solo album. Much like Tha Carter, the optimistic, club-ready uptempo of the Mannie Fresh era—replete with sunny videos, each rapper resplendent in expensive gems— was stripped down.

The new wealth imagery was replaced with the stark appearances of urban poverty, the harrowing realities of Birdman's “Neck of the Woods”—Uptown New Orleans. It was an indication that while Wayne was the fresh face of hope for new Cash Money, and the money was still coming in, the focus had returned to the streets. Cash Money wasn't about to cross over and sell out.

Wayne's lyric writing, at this point, was just hitting its stride, with unexpected rhyme schemes and clever, writerly details that emphasized a growing darkness. The song's opening lines: “Gangsta to the core/Ankle wrap flamer/Paint your kitchen floor/With your whore/Shit you can't ignore.” Birdman's bars had taken a turn toward the morbid as well, ending the song on a particularly bleak note: “It's where they hustle and the homies try to get it right/It's when you gotta ride/It's when the homie die/And the money can't stop the pain in the inside.”

Album: I Got That Work

Producer: Mannie Fresh

While unrepentant misogyny, constant threats of violence, and unapologetic materialism dominate the Cash Money library, the Big Tymers blew it up to borderline cartoonish proportions. Cars became spaceships, everyone was draped in diamonds and platinum, and every headrest had a TV in it. “Get Your Roll On” was an automobile-focused celebration of excess. The song relies primarily on a catchy stop-start flow, in which “Ro. Lex.” is rhymed with “Mo. Sex.” In 2014's flowjacking epidemic climate, it's hard to imagine that a track like this wouldn't have inspired hundreds of imitators had it been released today.

Album: Take Care

Producer: T-Minus

To the cultural mainstream, “HYFR” will outlast its musical attributes as a generator of memes: The footage of Drake at his Bar Mitzvah still pops up in GIF format at least once a week. The song itself was never one of Drake's biggest singles on the pop charts, its beat more a sidestep than a banger and the chorus as radio-unfriendly as they come.

But for Drake's core audience, it was a showcase for lyrics that soon became fan favorites: “All my exes live in Texas like I'm George Strait,” and “I've learned that working with the negatives can make for better pictures.” It's archetypal Drake music, where communication is all about texts and regrets: “I think I texted her” and “time for me to revisit the past.” Wayne's verse sticks more to the aphoristic, occasionally perusing notebooks for lyrics at the bottom of his sock drawer (“Met a female dragon, had a fire conversation”).

Album: Uptown 4 Life

Producer: Mannie Fresh

UNLV was a trio—Tec-9, Lil Ya, and Yella Boy—whose 1993 debut was a regional success, helping to fund the initial success of Cash Money Records. They released four albums with Cash Money, the first of which was among the first to meld gangster rap and bounce music in New Orleans, while Mannie crafted their beats. But it was Mystikal diss track “Drag 'Em in the River,” from their final CM record, Uptown 4 Life, that has sustained as the group's most celebrated song, and was even rumored to have inspired Juvenile to seek out and sign to Cash Money. Over the course of more than six minutes of “Dragnet” melodic licks (bounce music was built upon the Show Boys “Drag Rap”) and what sounds like Mannie shouting “OHH!” the three rappers threatened Mystikal with bodily harm, called him a hoe, and even said they would unwrap his braids. Mystikal at this point was signed to Big Boy Records, with whom Cash Money had been beefing since UNLV's debut accused Big Boy rappers Partners-N-Crime of jacking the UNLV style.

Album: N/A

Producer: Boi-1da, Frank Dukes, 40, Nineeten85

Where can you go when you're on top? Drake's been at the game's apex for a long time; several of the game's biggest rappers—Meek Mill, A$AP Rocky, French Montana, and 2 Chainz—all owe their biggest radio hits to Drake. In an era where EDM swiped pop music out from underneath hip-hop, Drake has been the only artist to sustain repeated forays into the Top 10 over the past five years. While fans argue over his recorded peak, he continues to make hit records. With “0 to 100,” producers Boi-1da, Frank Dukes, 40, and Nineteen85 wed a disorienting guitar loop to the snapping drums reminiscent of “Started From the Bottom” for a bit of tempered aggression. Halfway through, it slips into more comfortable clothing, with Drake spending more time considering his place from all the angles. A little neurotic, sure. But that space still feels secure.

Album: I Got That Work

Producer: Mannie Fresh

For the Big Tymers, stunting was a celebration that needed to be balanced with comedic edge. Sometimes—like old “adult” comedy records—the humor felt a little like being punched in the gut, leaving you unsure as to whether you should even be laughing. But either way, it was undeniable: Mannie's winking punchlines in balance with Baby's ineffable street-savvy id. The connection with comedy was made even more explicit in the “#1 Stunna” video, which came with the Kings of Comedy DVD and featured Steve Harvey, D.L. Hughly, and Cedric the Entertainer; it was also readily apparent when compared with the more serious gangster rap context of the Hot Boyz albums. But the real humor of “#1 Stunna” is evident mainly in the next-level absurdity of the lifestyle represented, which reaches its logical outer limit in Birdman's now-classic outro ad-libs: “I just bought me a platinum football field.”

Album: 400 Degreez

Producer: Mannie Fresh

400 Degreez was one of the best-selling hip-hop records of all time. It's also one of those rare releases where the album cuts are as strong as the singles, as was the case with the title track. The talk box chorus proves less is more: Just when you expect a hook as forceful as Juvenile's rapping, the robotic vocals ease in. No doubt Mannie Fresh was having fun in the studio, but the record's menacing feel keeps it from ever feeling like a joke: “Only God knows what the future might bring.”

Album: Chopper City in the Ghetto

Producer: Mannie Fresh

Of all the Hot Boyz, B.G. was the grimiest. He was a less acrobatic spitter than Juvenile, the one rapper who returned most frequently to the language of violence. His raspy vocal style and lyrical directness were frightening, an aesthetic refusal to mediate his art through any filter. What he portrayed was raw and uncut, murderous threats delivered with unnerving casualness. Although “Bling Bling” would catapult B.G.'s Chopper City in the Ghetto to platinum sales, “Cash Money Is an Army” was more representative of the bleak sound that record contained. Only the faintest whispers of emotion are hinted at beneath B.G.'s grizzled armor: “I know I'm tired of these bitches trying to get me killed/I know I'm tired of these stanking hoes smiling in my grill.”

Album: Juve the Great

Producer: Dani Kartel

Even though Juvenile's 400 Degreez was a quadruple-platinum monster—to this day, the best-selling album Cash Money produced—it wasn't until 2003 that the rapper was able to top the pops. "Slow Motion" featured Soulja Slim, who had started out rapping in New Orleans with Big Boy records, before being picked up by No Limit and ultimately going independent in the early 2000s. The song was supposed to be Soulja Slim's, and it was one he'd had faith in.

Juvenile explained to Complex how the record came to his album: “He went to my brother and said, ‘Tell your brother that if I do the song for Koch, they’re not gonna push this record how it needs to be pushed.’ He wanted that song to go through Universal’s system. Dude was smart. He knew that if the song went on my album he would blow up. If it was on his album, it probably won’t get heard by everybody. I took the song, listened to what he was saying, and said, ‘You know what, you’re right.’”

“Slow Motion” wasn't just Juvenile's first No. 1, but the first rap song from New Orleans to reach No. 1 as well, and a fitting farewell to Soulja Slim.

Album: Take Care

Producer: Noah “40” Shebib

Take Care was the most anticipated rap album of the year when “Marvin's Room” arrived in the summer of 2011. The record immediately set a different tone. One part rapped to two parts sung, the song was a murky tale of irresponsible drunk dialing—an extremely odd juxtaposition for an art form known for bragging. It's a strange contradiction: Is Drake putting insecurities on display in an attempt to be more real? Is he being perversely proud or passive aggressive? No matter your interpretation, Drake turned hip-hop's club obsession inward, writing about the kind of clubbing that usually goes on between the lines of most party rap—the petty jealousies, the loosed emotions.

Album: Hood Rich

Producer: Mannie Fresh

The Big Tymers' most famous single managed to tone down their typically context-free consumerist tendencies for a celebration of living large even when you couldn't afford to. No doubt this was in part a response to the backlash against “Bling Bling”'s extreme flashiness—or at least, a significantly tamer, more knowing, Mannie Fresh'd version of it. But if anyone missed the unrepentant stunting of their earlier records, the transition to self-awareness about the universal obsession to be fly in any socioeconomic bracket was eased by the music. “Stay Fly” was one of Mannie Fresh's most immediate pop singles ever, transforming the theme from Gilligan's Island into a massive hit that felt as large as the life to which its protagonists aspired.

Album: Tha Carter

Producer: Mannie Fresh

With Jay Z's retirement underway, Lil Wayne's style shifted from that fast, slang-heavy, drawling New Orleans deliver to a slowed, centered, mainstream-friendly one—thanks in part to the creative experimentation of the early '00s Sqad Up tapes, which ought to rank with G-Unit's mixtape run as some of the most important of the early 2000s. Aided by rappers like Mikkey Halsted, then a member of Cash Money, Wayne's style had developed in a way that drew more attention to how clever he really was, beginning a run that culminated in unparalleled commercial—and ultimately, critical—success.

If the Sqad Up tapes were his emergence, Tha Carter was his official arrival. He was not yet calling himself the Best Rapper Alive, nor had the drugs sparked his later experimental period. Instead, it was the beginnings of a new regime at Cash Money. With Juvenile and B.G. gone, Turk behind bars, and Mannie Fresh with one foot out the door, “Go DJ” was the beginning of a whole new era. The video, shot in a prison, announced the new direction; the bling was bare, Mannie's beat dryer and more conservative, the textures again returning to the streets as Weezy stepped into his prime.

Album: Birdman

Producer: The Neptunes

For his second solo album—his first came out as B-32, in 1993—the No. 1 Stunna still went by Baby, but was in the process of rebranding himself as the Birdman. This, of course, lead to one of the most ridiculous album covers in the history of Cash Money. But it was a strong album, and although Mannie was still crafting the bulk of the beats, it was the Neptunes-produced banger “What Happened to That Boy” which sustains for most fans. Although the Neptunes' masterful bleeping riff/bongos combo beat and nonchalant Clipse guest spot make it sound more like a cut off Lord Willing, the birdcall hook has a distinctly Big Tymers-esque absurdity that puts it in the rarefied air of even the best '02-era Clipse records.

Album: We the Best Forever

Producer: T-Minus, Noah “40” Shebib, Nikhil S.

Until We the Best Forever in 2011, DJ Khaled was an independent entity. But with a major label deal through Young Money/Cash Money Records, Khaled managed to get his mitts on one of the best songs of his career with “I'm on One.” The song was a massive success, although like most hip-hop singles in 2014, hitting No. 1 on the hip-hop charts was only enough to scrape into the bottom of the Top 40. Listening to rap radio that summer, the song's twilight ambience was everywhere, a musical linen suit on a hot summer night. The only thing that remains a mystery is why Drake gave this one away.

Album: Tha Carter III

Producer: Jim Jonsin & Deezle

While “A Milli” remains the critical stan favorite, “Lollipop” was Lil Wayne's biggest crossover single ever, and deservedly so. No song Wayne ever released so effortlessly married an accessible melody with the more radical aesthetic maneuvers he attempted on this song. It also helps to explain why “Lollipop” is actually one of the rapper's most influential records. In its slurred, drunken euphoria, it's easy to extract the DNA of Future, Chief Keef, Young Thug, and a hundred other singles of the Southern hip-hop diaspora. And part of this credit goes to Static Major, the underrated singer/songwriter who worked on some of Aaliyah's best singles, and managed to somehow transform his swan song (he died of a brain aneurysm later that year) into the biggest hit of not just his career, but Wayne's as well.

Album: Like Father, Like Son

Producer: T-Mix

By the time Birdman and Wayne's Like Father, Like Son hit the shelves, anything Wayne-related was hot. Wayne was shifting, at this point, from the sober brutality of Tha Carter and its portentous precision into a new phase. Suddenly, the energy had doubled. The rapping came at a faster pace and the vocal sample in the background ramped up the adrenaline: “If your mans wanna play I'mma fuck around and put that boy's brains on the gate/Hey pick em up! Fuck em, let em lay/Where I'm from we see a fucking dead body everyday.”

Album: Chopper City in the Ghetto

Producer: Mannie Fresh

Although overshadowed by its own title—which managed to transcend its originators in becoming a catchy and ultimately corny shorthand for hip-hop materialism—B.G.'s “Bling Bling” is one of the greatest singles of mid-period, post-Universal Records deal Cash Money. It features the entire CMR lineup of that era, relies on some of Mannie Fresh's most distinctive production work, and became an all-conquering smash record. It's endlessly quotable (“Hit the club, light the bitch up/Cash Money motto: drink til you throw up!” and “I be that nigga with the ice on me/If it cost less than 20, it don't look right on me.") and the sparkling production—from the synthesizer stabs to gurgling effects—perfectly reflects the song's concept. From Baby's opening to Wayne's coda, “Bling Bling” epitomizes the unrestrained, unapologetic flashiness of Cash Money in all its glory.

Album: Tha Carter III

Producer: Bangladesh

Lil Wayne may remain a creative force in 2014, but even the most avid stan would have to admit that his true moment of peak cultural relevance was the release of the “A Milli”/“Lollipop” single, a two-sided monster that ranks up with Run–D.M.C.’s “It's Like That”/“Sucker MCs,” and Eric B. & Rakim’s “Eric B Is President”/“My Melody” for showcasing an artist at his best on a single 12” record. A distinct masterpiece that celebrated one of hip-hop's most wigged out performers firing on all cylinders, “A Milli” seems as strange today as it did the moment it was released. A chorus-free single with a singular abrasive Phife-sampling vocal loop, it was raw rapping-for-rapping's sake exercise that—like many legendary tracks before it—proved the musicality of music without melody. It deserved all of the hype directed its way, a pure distillation of hip-hop's subversive promise.

Album: 400 Degreez

Producer: Mannie Fresh

The Mannie Fresh era of Cash Money's dominance was known for building upon New Orleans' bounce heritage. But no bounce-based record was so perfectly able to embody the form while crossing over to the largest possible audience as “Back That Azz Up.” The drums came straight from bounce, but the melodies had a different inspiration. “I was thinking along the lines of…how do I get bounce music to everybody? How do I get it to old white ladies, where they'll be like, 'Oh shit, I like this song'?” Mannie Fresh asked rhetorically during an interview with Red Bull. The answer was obvious: “Classical music!” Thus came the pizzicato strings in the foreground, while the strings in the background were swiped from UGK's “Protect and Serve.”

The song, of course, was a true pop culture phenomenon, and accomplished just what Mannie had hoped for. “I remember Sharon Stone saying in an interview that 'Back That Azz Up' was one of her favorite songs,” Mannie recalled. And the song's status has sustained, the go-to club jam for any instant party starter, it's one of those records identifiable immediately by those opening strings. To this day, it remains a club staple in a way few songs have. Mannie may have grabbed something else from classical music as well: cultural longevity.

Album: 400 Degreez

Producer: Mannie Fresh

For his breakout single on the national stage, Juvenile's “Ha” still seems an unlikely contender. To this day, it sounds like a transmission from another world. It was a futurist statement that made year-old songs sound like ancient relics. At the same time, the song was timeless; Mannie's percussive textures had the heft and feel of a stone or concrete block, hearkening back to the burnt out terrain of hip-hop's origins in the Bronx as much as it did to Juvenile's own Magnolia projects. The song was most striking for its tonal ambiguity—stark and unrelenting, with Juvenile coasting through the groove as if he'd only ever been comfortable in constant motion.