Years before the superstardom of hits such as Black and Yellow or See You Again, Wiz Khalifa was signed to Rostrum Records and searching for his niche. The young Pittsburgh native released several mixtapes prior to 2009 which generally failed to impress but showed a lot of potential. He had a unique balance of old school, soulful hip-hop and a fun, youthful flair. I’m also sure it goes without saying that he really likes weed. With clear influences in Bone Thugz & Harmony, Juicy J, and Snoop Dogg, Wiz would finally breakthrough in 2009 with the release of How Fly and begin one of the genre’s greatest mixtape runs (culminating in classics such as Kush & OJ and Taylor Allderice).
Fellow stoner Curren$y had also begun to make a name for himself down south. Following collaborations with Lil Wayne and a spot on the XXL Freshman List, the New Orleans native was following a similar trajectory to Wiz. With each gaining some prolificity in their lanes, their collaboration would convince the game that they had a place among the genre’s best.
All it takes is one look at the Cheech & Chong inspired cover art of this mixtape to know what you’re in for. Two of hip-hop’s most promising young MC’s and the game’s biggest stoners had teamed up to deliver 53 minutes of soulful, vintage weed raps with an aviation inspired theme. It contains terribly dated references to sports, video games, and more which give it a lot of character. Wiz and Curren$y also show vast knowledge and respect for the genre through countless interpolations and references to classics.
The production is old school smooth, with beats mostly provided by Big Chop, Sledgren, Monsta Beatz (a frequent Curren$y collaborator), and even a gem from DJ Hi-Tek to wrap it all up. The samples are varied and soulful, often sounding straight out of a 60’s movie soundtrack and remaining true to the aviation theme. It all feels like a victory lap by two kids who really hadn’t made it yet, but they were hungry, confident, and clearly on the way up.
This is an album that I’m sure many of you have a lot of nostalgia for. Whether it was cruising around town on a summer day, vibing with your girl, or obviously rolling one up, there was something for everyone. It was the soundtrack to so many peoples’ adolescence and defined a fun, unique era for hip-hop that the average kid could relate to (alongside artists such as Kid Cudi, Blu, and early Drake). Beyond that, this tape was arguably the crown jewel of the Blog Era and helped the two rise to fame in the early 10’s mixtape scene. Wiz was pretty much the DatPiff poster boy for years.
Now Curren$y is always great but feel that Wiz really steals the show on this whole tape. His melodic flows, endearing lyrics, and memorable hooks are just so infectious. However, Spitta definitely holds his own and provides a more grounded, southern flavor (with consistently better bars even) which contrasts perfectly with Wiz’s huge energy. Their chemistry was really authentic, and they clearly had a lot of fun making this record.
Clear the runway, baby! It’s just an iconic opener. Wiz comes in with such infectious delivery which leads up to a subtle beat drop. His prolonged, melodic rhymes do a lot to add personality and the hook is an ear worm. Curren$y brings his signature, lazy southern style and a really impressive rhyme scheme. The beat has so many layers: a short, high pitched vocal sample from Smokey Robinson, subtle whistles, and horns. At the end of the hook, it all chops into a short loop that just culminates perfectly. This is easily one of my favorite intro tracks ever and it’s an absolute classic.
The Check Point
But I don’t do drugs – just weed, Caution flags wave, and fuck it I still speed
And proceed to give them what they waiting for
Daytona 500 guess who lighting joints up in the pace car
Play hard, but I work way harder to afford
This track has a very similar vibe to Car Service but that doesn’t do anything to detract from its quality. Another high vocal sample and triumphant tones fill the quota. Curren$y comes through with what might be his best performance on the tape here, with clever flexes and some unexpected references. Wiz’s singing on the hook is a bit grating, but the lyrics are still touching and make up for it to an extent. “The Check Point” emphasizes an important theme on this tape: Living without regrets and striving for your dreams. Their chemistry is palpable, and it feel like you can see yourself in them. The hunger, the laidback vibes, and youthful confidence come together to form something special throughout the tape.
Fly N—-s Do Fly Things
This beat has an interesting lo-fi quality to it and some really well done drums. They drive everything along nicely and have some subtle bounce. Wiz’s verse starts off a little bit clunky and off beat, but he quickly catches up and delivers well enough. Curren$y comes in with a simple but catchy and clever hook, continuing the album’s aviation themes. He also interpolates the staple hip-hop line, “On the road to riches and diamond rings” from both Biggie and Kanye. He has another strong verse, shouting out Wale and referencing the famous Hype Williams film Belly.
In the Middle
Produced by Big Chop, this has to be the tape’s standout beat. Sharing a sample with Snoop Dogg’s “Who Am I” — albeit with far less distorted horns — it feels remarkably cinematic. It perfectly elicits the image of an old-school airport or even a campy spy movie. Spitta pays further homage to Snoop as he quotes his verse on “G’z Up Hoes Down”. Both come through with their typical subject matter and quality on here, as well as a hook interpolating Andre 3000 on “2 Dope Boyz”. Wiz and Curren$y are clearly students of the game with how much knowledge and respect for the culture they display on this tape. Something you might not have expected from two young, fun-loving stoners relatively new to the scene. The beat really steals the show on this track but both MC’s do well enough to not drag it down at all.
You’ve probably noticed a pattern by now: There’s nothing particularly profound or varied on this tape but it consistently delivers on its promise of fun, laidback tracks. “Layover” is no exception with its dreamy production and Wiz’s cheeky bars. What stands out on this track is their delivery as they intentionally break flow (Spitta at the end of his verse saying, “on a quest like Johnny and Hadgi” and Wiz separating the syllables of “octane”). While a small detail, this adds some subtle variety to a tape with relatively generic themes and structure while showing off their technical skills.
Now here’s a lighthearted, romantic track. The short, bouncy loop on the beat nicely evokes the image of a fun night on the town. Curren$y sets the scene of his player lifestyle, describing raiding his girl’s fridge, playing her son’s PS3, and brushing his teeth in the car. Wiz comes in with a really impressive flow and simple, but effective rhyme scheme. He presents a more luxurious twist on Curren$y’s verse as he speaks on his romantic life as a young star.
Another track for the ladies, “Friendly” is a perfect example of the pair’s chemistry. Curren$y shouting out Wiz’s hometown Steelers and references across their verses to Batman make it evident how fun and genuine their friendship is. The beat has a lot going on: Subtle details and the numerous layers give off a scenic, whimsical feeling, although some might find it a bit too busy. The hook is catchy but a bit grating with how distorted it is.
Surface to Air
Smoke filled rooms
Camera lens zoom, from a mile away you can smell the fumes
College girls play me in their iPod or Zune
Even bitches with bad attitudes bumping to our tunes
They high maintenance
Give ‘em wings let ‘em fly places
Introduce you to high times, flavors, and skyscrapers
“Surface to Air” has a noir sound similar to “In the Middle” with its rolling, aquatic beat. Curren$y uses missiles as a metaphor for the two star’s meteoric rise to the top in rap while resisting the ills of the industry (“It’s amazing how I get so high and stay so down to Earth”).
Over the Building
In contrast with “Surface to Air”, this track sees the two looking down on the game from their newfound star status. Taking aim at critics (“All them fools make is weed songs”), referencing paparazzi, and never looking back as they speed past the competition. This is another particularly strong beat with its light acoustic guitar and prominent drums.
A beautiful vocal sample of The Jaggerz’ “Memoirs of the Traveler” on this beat (courtesy of DJ Hi-Tek) makes “Rollin’ Up” the tape’s most essential smoking track. How Fly closes on a somewhat introspective note by Wiz and Spitta’s standards. Wiz discusses the loneliness of fame: Fake friends, women who don’t truly care about you, and memories of poverty. The two find relief in weed and eachother as they unapologetically commit to their journey and live life to the fullest.
How Fly isn’t just an album about getting high. It’s about staying true to yourself, forging connections, and chasing your dreams — Things that every listener should be able to relate to. For Wiz Khalifa and Curren$y, it was the start of a legendary run that thrust them into the spotlight. For many people, this project represents a special time in our lives. Youthful and carefree, it was the soundtrack to your high school smoke sessions, road trips, dumb love, and simpler times. Even if you’re just now listening, How Fly is mandatory listening for smokers, the backdrop to treasured memories, and the quintessential mixtape of its era.
Listen to How Fly