Wiz Khalifa's Musical Evolution In 15 Songs

Few rappers of the 2000s can claim to have the career longevity, impact, and diversity of catalog as Wiz Khalifa. In a story that defies the typical tropes of rap success, Wiz went from a teen chancer hailing from Pittsburg (hardly a megacenter for rap, even after his successes) to a household name with various hit singles and even a Grammy nomination. While Wiz's easy-going and relatable style as well as his love and promotion of smoking weed became integral to his persona and music, his success depended equally on his ability to adapt to many different styles, unabashedly and often with little effort. The average rapper might have one or two tricks under their sleeve after all, but since debuting on the scene in 2005, Wiz has gone through so many different approaches as a rapper, in a way that not many others can do, let alone that their fanbases would allow (!).

We’re taking the time out to go over the fascinating career of Wiz Khalifa, the master of chameleon-like adaptation in rap, and trying to study every move in the Khalifa playbook. From proto-EDM Rap, post-hyphy, trap, pop and beyond, this is a timeline in the musical life of the Taylor Gang OG himself. Scroll through with us.

In 05, Wiz’s proper debut on the rap scene commenced with the mixtape Prince of the City: Welcome to Pistolvania. The beginning of Wiz’s relationship with independent label Rostrum Records, it’s hard to imagine that THIS would be the Wiz Khalifa who managed to become a star. Tell casual music fans or listeners about "Too-Tall Tee" era Wiz and they’d probably do a double take; play tracks such as “53rd” off this mixtape, where Wiz and a young Chevy Woods (then going by the name Kev da Hustla) and they’d probably either have a stroke, die laughing, or a combo of the two. It’s not that hearing Wiz bark into the mic like he thinks he’s Hell Rell is inherently ridiculous by itself, it’s just the vicious contrast between his early tough talking and his current ‘cool guy’ persona is quite the leap.

After about a year or so of putting out material, Wiz eventually shifted to his second phase which is a lot closer to the Wiz Khalifa we’ve all come to know, but still not quite at his full star power. By this time, a surprising amount of buzz would result in Wiz Khalifa being courted by labels and signing with Warner Bros. for a brief period of time. Part of this was based off Wiz’s already rapidly developing polish into a rapper with melodic sensibilities, who relied more on charisma and flow than the barky bar-spitter we heard just before. Records such as “Time Goes By” show a Khalifa with one foot in those aggressive beginnings but another foot forward, towards the rapper we’d come to know today.

During his tenure at Warner Bros. a few buzz singles were released that certainly demonstrated that Wiz was a potential superstar, but didn’t become certifiable smashes by any stretch of the imagination. While the first single “Youngin’ On His Grind” was more street rap (albeit in a more southern-influenced direction), his other noteworthy single from this era was the flashy “Say Yeah.” Armed with little more than a track which hijacks cheese trance banger supreme, Alice Deejay’s “Better Off Alone,” Wiz sounded perfectly competent and happy to tackle the commercial hemisphere, and to be honest, it’s only real offense is that the record is just a few too years too early. Were Wiz capable of waiting it out and hopping on Daft Punk or Justice like some of his contemporaries did, perhaps he actually would’ve proven to be on the mark. That said, “Say Yeah” is a fun little afternote that, although coming much too soon, certainly hinted at what was to come.

If you’ve followed Wiz for more than a few years, you know a major influence on his evolution to the rapper he is today is none other than Harlem’s finest, Max B. A huge enthusiast for the Silver Surfer’s smoked out anthems, he’s by far one of the rapper’s biggest advocates in the game, next to frequent collaborators such as French Montana or Dame Grease. That said, the duo managed to get on record together before Max’s incarceration. Produced by Wiz’s main collaborator of the early days, Johnny Juliano, “Watcha Lookin’ At” actually belongs to a group known as The Finest who never quite had a career at the heights of their features, but it’s almost a perfect meeting point for where Wiz was at this point in time, along with Bigavelli. Over squealing synths, the duo trade verses with sleazy good humor, displaying a counterbalance that should Max ever get out of jail, would probably be musical gold.

Ultimately, Wiz and Warner Bros. turned out to be a bad fit, and the rapper would find himself back to square one. Of course, by this point he’d developed immeasurably as an artist, and established various connections in the industry. One such connection that has endured for almost a decade is his relationship with one Shante “Curren$y” Franklin, who at this time was still fresh off a departure from Cash Money Records as an affiliate with Lil Wayne. Together, the duo united for How Fly, a mixtape that remains an essential record in both men’s catalogs still to this day. Next to the king of Pilot Rap, Wiz’s approach to rap was getting refined further and further, into a more commercial and universal sounding approach without sacrificing the essential elements of what made people fans of him in the first place. On a track like “Huey Newton,” you not only hear the beginning of a beautiful relationship, but the true emergence of Wiz the superstar.

One of the most important strengths in Wiz Khalifa’s output is his adaptability. There aren’t too many other rappers since or alongside him who have that same level of innate instinct on different styles of production. You can say Wiz attempting different styles isn’t what you want from him or even comes off a bit corny, but the guy almost always sounds perfectly in the pocket for any sort of record he writes to. Such an ability to be a stylistic chameleon helped in an age where rap audiences were so fragmented that one had to make a different record for every ‘type’ of fan. A cut from his fan-favorite Burn After Rolling tape, Khalifa’s “The Thrill” takes a cut from indie electro act Empire of the Sun and turns it into an effective party rap jam that was perfectly suitable for the kind of people refreshing 2dopeboyz as well as the one’s scrolling along through Pitchfork. It's the strategic versatility that made Wiz feel like a rapper who could appeal to just about everyone.

Whether a longtime fan or a recent convert, most would agree that few of Wiz’s mixtapes (or even albums) cemented his career as effectively as Kush and OJ did. Easily one of the biggest mixtapes of its time, the success of that tape seemingly overruled any prior successes from Wiz and now made him one of the hottest commodities in rap. It’s not hard to understand why, considering the various smooth tracks that showcased Wiz’s masterful flow over delicate R&B sample chops, a perfect soundtrack for cruising, smoking, or whatever sort of antics one gets into. On a track like “Visions,” you can hear a Wiz that’s unmistakably hungry and eager to seize the moment after having built so much momentum without the support of a major label, or any sort of industry push. Now it’s surprising to think Wiz has spent more time signed to labels than he’s been without, because his underdog spirit was once such a defining aspect of his career and truly shone through on tracks such as this.

Arguably one of the biggest reasons for Wiz’s grind taking as long as it did, was that Pittsburgh was not only an unpopular part of the country-- it was also not The South. From about '03 onward in the US, it felt like any rapper coming out of a state beneath the Mason-Dixon line could usually get himself a brief hit on MTV; meanwhile, the amount of stars emerging out of say, the Tri-State area were few and far between, more often than not being relegated to mixtapes and often pitted against the Southern Rappers in a contemptuous fashion. To his credit, Wiz never fell for the pitfall of becoming a ‘young oldhead,’ and instead chose to embrace the climate he was surrounded by, collaborating with production teams such as the Dungeon Family or Juicy J of Three Six Mafia who were respectable veterans of the South but also weren’t too outlandish for him. A classic cut featuring Juicy behind the boards and on the mic , “In My Car” is a throwback to the ‘Play me some Pimpin’ mayne’ era of Juicy J’s career resurgence, and a point of origin for the duo eventually joining forces, with Juicy becoming a key member of the slowly building Taylor Gang team.

By the time 2011 had rolled around, Wiz was unmistakably ready for the mainstream. After the massive success of his “Black & Yellow” single, anticipation was immeasurably high for Wiz and everything seemed to be a sure shot. Of course, backlash was inevitable and so while his proper debut album Rolling Papers was a success, there was a lot of huffing and nagging from fans, as well as critics, who found it somehow "too commercial." Looking back, this is both understandable, but not even the peak of commerciality we'd see from Wiz. Even a single like “Roll Up,” though certainly sugary pop, is none too outlandish. Say what you will about the song’s hazy synth-pop vibes, or the goofy earnestness of Wiz on the track, but it’s a heck of a lot better than “Young, Wild and Free."

In 2011, I can think of few rappers who were less ‘in demand’ for features on a major label album than Bay Area legend Too $hort. Not a snub against the legend who gave us so many classics since the mid-80s, but one wouldn’t think that gesture would translate to the sea of millennials who might’ve been too young to remember his early classics or even his hyphy-era comeback. Nevertheless, one of Rolling Papers finest (and weirdest) moments is the single "On My Level," a murky cruiser featuring the pimp rap pioneer himself. Wiz, for his part, has always taken great pains to pay tribute to the older rap icons who’ve inspired him, such as Snoop, Cam’ron, Juicy, Short and many others. It’s fascinating to hear such a stark and gloomy record get pushed to the top off the charts just off the strength of Khalifa’s then-massive hype.

As much as Wiz’s sound was reaching a commercial endpoint, the landscape around him was changing, and to his credit, Khalifa took notice. By this point, the late 00s demand for poppy, commercial raps were shifting over to the new aggressive sounds of trap being spearheaded by Lex Luger’s productions for Waka Flocka and Rick Ross. Thankfully for Wiz, he had an easy in with Luger in Juicy J. The Rubbaband Business mixtape series with Luger had reversed Juicy's career trajectory from becoming aged veteran to surprising popularity. In the first of Wiz's Cabin Fever series, the rapper fully embraced the trap sound with ease, and gave his career new legs in the process, finding an audience who were probably never going to engage with Wiz’s mainstream material at that point. For Luger, it helped ramp up a demand that was already sky-high, and for Wiz, it did a lot of damage control in the wake of fickle fans thinking he’d "sold out" by embracing a whole new fanbase altogether.

By 2012, the Luger style of trap was already starting to ebb away and lose popularity in favor of weirder styles, which would soon become the standard. Of course by this time, Wiz was already quickly learning to adapt again and again, keeping his eyes on every potential trend and style to keep himself fresh, not only continuing his musical output but signing the likes of Ty Dolla $ign and Berner to the Taylor Gang roster. Naturally, affiliating with those two put him in close proximity to the growing ratchet sound emerging out of California, helmed by the likes of DJ Mustard, The Invasion and League of Starz. As a result, Cabin Fever 2 found Wiz abandoning aggro-trap in favor of slicked post-hyphy grooves, a much more suitable environment for Wiz’s playful flow-switches. “Bout Me”, featuring Iamsu! and Problem (both hot off their joint tape Million Dollar Afro at the time), is a slept-on classic in the ever-expanding Wiz catalog, demonstrating just how effectively he could soak up game.

If you thought somehow by this point, fatigue was starting to show for Wiz, you’d be wrong. His third album Blacc Hollywood was doing strong, particularly off the fact that Wiz somehow managed to make the Drill sound a perfectly suitable home for him. After having already sounded surprisingly comfortable on Chief Keef’s single “I Hate Being Sober” (well, maybe not that surprising), Wiz would enlist Keef’s then-frequent producer Young Chop for his own take on the genre “We Dem Boyz.” While certainly much more ambiguous as to the potential for danger when compared to the Chiraq output, Wiz clued in on the anthemic surges of the genre and made one of the biggest bangers of his career. Considering at that point he was nearing a decade in the music business, and he still managed to stay on the pulse of the trends, it was a pretty impressive maneuver.

Produced by Ritz Reynolds, “Call Waiting” is off Wiz’s 2016 album Khalifa and is one of the more interesting sort of diversions in the rapper’s discography. He’s done material before, such as “Up” off Kush and OJ, where pure singing has taken up the entirety of the track. Yet here, not only has his crooning improved from those early days, it’s also over a tasteful southern soul arrangement, the kind of thing Willie Hutch or Bill Withers would’ve produced. Listening to Wiz attempt this sort of proper, adult-oriented sound is maybe the closest thing to "experimental" that he’s ever attempted, besides the occasional odd one-off leak like the proggy “Refresh / Say No More.” In this case, though, Wiz found it suitable to release the track officially. It’s still kind of a bizarre moment but in later years, who knows if this will become a full-fledged project, the way that his hero Snoop Dogg’s often diverted his attention into various forms of R&B.

The last few years have seen Wiz Khalifa’s popularity not wane as much as ease away from the immediate conversation, but he’s still remained a rapper who is always one step beside the current day conversations. Whether it’s through new artist affiliations such as Sosamann of the Sauce Twinz or producers such as Cardo, TM88 or Sledgren, he’s managed to keep himself connected to rap scenes all over the country. One artist he was supposedly courting before his untimely death was the next star emerging from Pittsburgh, Jimmy Wopo. That said, in a bittersweet turn, Wiz managed to feature both Wopo and another Pittsburgh up and comer Hardo on “Blue Hunnids” from his recent album Rolling Papers 2. It’s an interesting return back to the hard-nosed rap styles Wiz initially came up on over a decade ago, with a modern twist. Given how Wiz is approaching close to 15 years in the rap game, and has gone from rising buzz artist to almost an elder statesman, maybe it’s fitting we close this out with a record that demonstrates his growth by echoing his past.