Hip-hop has had a slew of superstars emerge this decade, but few have a resume that stacks up to that of Taylor Gang general Wiz Khalifa. It's not everyday that a rapper is nominated for a Golden Globe or racks up over a billion plays on a YouTube video and those are just some of his most recent accomplishments. The 28-year old rapper has everything that an artist can ask for: hits galore, a devoted fanbase, magazine covers and all the other perks that being at the top of your game brings. Wiz has got it made.

But while things may look better than ever, none of it was given and he's paid his share of dues to get the top billing that his name now carries. Beginning his rap career as a precocious rhyme animal in his hometown of Pittsburgh, Penn., Wiz found a fan in Benjy Grinberg, a former assistant to L.A. Reid and the head of indie label, Rostrum Records. Grinberg, who received word of Khalifa's talents from a high school friend, scooped up the then 17-year-old MC in 2005, and they released his debut mixtape, Prince of the City: Welcome to Pistolvania.

The buzz from Prince of the City and his debut album, Show and Prove, led to a deal with Warner Bros. Records, but failed to yield an album release, prompting Khalifa to split from the label in 2009. The split proved to be a blessing in disguise for Wiz, who had been cultivating a following off the strength of mixtapes like Prince of the City 2, Star Power and Flight School. Wiz's choice to bet on himself would pay off big with the release of Kush & Orange Juice in 2010, which broke the internet and led to him becoming a household name, culminating in a new deal with Atlantic Records and the rest is history.

The 10-time Grammy nominee has enjoyed a career that is littered with platinum and gold plaques and is the author behind some of the biggest songs in all of music over the past five years. Having cemented himself as one of the most successful rappers of his generation, XXL gives Wiz his just due by highlighting the best songs he's recorded in his career. Here are 20 Best Wiz Khalifa Songs.

  • "Pittsburgh Sound"

    Wiz Khalifa

    In 2006, Wiz Khalifa was just another aspiring rapper looking to be heard and make his mark on the rap game. Regarded as a rap prodigy in his hometown of Pittsburgh, Wiz was scooped up and developed by indie label Rostrum Records, who would release the rapper's first album, Show and Prove. The LP would be a moderate success, but its lead single, "Pittsburgh Sound," managed to make a dent and position Khalifa as a promising MC, causing Warner Bros. Records to take notice and add him to their roster. Many fans may sleep on "Pittsburgh Sound" with Wiz's more high-profile material in the years since, but it remains an essential cut in his discography deserves inclusion on this list.

    "Around these parts I'm known as the youngest in charge / My tracks bang out the trunk of your car / It's the city's known rap spitta Semi blown clack niggas / Skin and bones but really known as that nigga," he rhymes.

  • "Say Yeah"

    Wiz Khalifa

    Wiz was a fixture in the local Pittsburgh rap scene, but his first taste of success on the national scene would come with his the release of his single, "Say Yeah." Piquing the interest of Warner Bros. Records in the aftermath generated from his Star Power mixtape, Wiz would ink a deal with the label in 2007 and service "Say Yeah" to the public in early 2008. Produced by Johnny Juliano, "Say Yeah," features a young and exuberant Wiz musing about popping bottles among a bevy of beautiful women and his crew in the club celebrating life. Setting the scene with lyrics like, "My niggas leaning, Diddy-bopping / Let's get it popping / I said lets get it popping / Just look at how she drop it, Little Mama a certified pro / She need her own show / Slide on down that pole and grind slow" and reeling listeners in with the hook, Wiz Khalifa makes a great first impression on the public on what would be his only single released during his time with Warner Bros.

  • "Boarding Pass"

    Wiz Khalifa

    His career hit a new peak after his 2009 mixtape, Flight School, touched down. Having cultivated his grassroots fanbase into a devoted following of rabid fans, Flight School serves as the genesis of Wiz's superb songwriting and represents an upward transition in his artistry. The mixtape's opener, "Boarding Pass," is a great example of the magic Wiz was cooking up. Attacking the track with vigor, Wiz has the confidence of a made man when he spits, "Where you goin when the driver know your last name / And first class ain't much different from the last plane / Say we the same but I'm nothin like you guys / Nigga, I'm a frequent flyer Taylor Gang or Drink n Drive...Die," marveling at his come-up. Flight School is packed with bangers, but "Boarding Pass" is the definitive selection and one of the Pittsburgh natives premier outings on wax.

  • "The Thrill"

    Wiz Khalifa

    After his departure from Warner Bros. Records, Wiz decided to bolster his buzz even more and attack the mixtape scene, releasing Burn After Rolling in November of 2007. The mixtape features a mix of the street-wise Wiz Khalifa favored by longtime fans and the guy that churns out smash pop records these days and is considered one of his best projects by longtime Taylor Gang disciples. One of the tape's superior moments is "The Thrill" a track on which Wiz tackles the Empire of the Sun song, "Walking On a Dream." Lyrics like, "Most girls wanna hide the fact that the thrill, they chase it / But you, just wanna get drunk tonight and fuck someone famous / So I just name a time and a place and your game for it / Value player, hotel room, meet you there" leave little secret to Wiz's intentions as he gets his philandering on with no shame, making "The Thrill" a definite keepsake for any Taylor Gang loyalist.

  • "This Plane"

    Wiz Khalifa

    Following years of false starts and push backs to his planned Warner Bros. album, First Flight, Wiz decided to part ways with the label in July of 2009 and continue the independent grind he'd been on with Rostrum. Wasting no time putting gears in motion, Wiz ended 2009 with a bang, dominating November with an album and mixtape. The album, Deal or No Deal, would be his second official LP and would find his stock rise on a mainstream level, peaking in the Top 10 of the Billboard Top Rap Albums chart and selling over 5,000 units in its first week with minimal promotion. The LP's lone single, "This Plane," would play a big part in those numbers and would widen Wiz's fanbase even further. "I'm screaming fuck them niggas who hated, I'm money affiliated / Speculating me landing, must have got me mistaken with lame niggas / Know you gone get high as fuck as long as the planes with you / Left that major situation alone and became richer," he raps. Wiz chucks the deuce to his haters while putting his days of label purgatory behind him.

  • "Homicide"

    Wiz Khalifa Featuring Chevy Woods

    Kush & Orange Juice may be Wiz Khalifa's most ballyhooed mixtape, but Cabin Fever remains the most anticipated project that he's ever released. Prior to dropping the mixtape, he previewed a song called "Homicide" on his web series, which sent fans into a frenzy and when the full version drop, it more than lived up to the hype. With Chevy Woods riding shotgun, Wiz goes in over the sinister DJ Spinz and RMB Justize-produced track and turns in one of his more addictive offering in his mixtape catalog. "I got my wings when I was young so I tend to fly / I put my chain on, they saying it's homicide / And I'm killin' 'em, it's homicide / I'm killin' 'em, it's homicide / I got my change up, they looking like they surprised / Niggas hatin' on me hard cause my paper right," he rhymes. Wiz doles out murderous bars with the calm of a smooth assassin. Leaving the naysayers without a case to make in regards to his rep as one of the best young stars in the game, "Homicide" more than gets the job done.

  • "Cabin Fever"

    Wiz Khalifa

    To get fans hyped up for his long-awaited Cabin Fever tape, Wiz dropped the title track to the project more than a year prior to its release and needless to say, the song did exactly what he intended. Produced by Lex Luger, "Cabin Fever" is a return to the more lyric-oriented style Wiz employed during his rise up the rap ranks and sees him upping the ante with a bevy of quotables that rate high on the Richter Scale. "Red hat, black chuck's, black 501's on / That's your baby momma, but her numbers in my iPhone / Yea I got a girl but I swear I need a newer bitch /Let her out the house and I'll be leaving here with your bitch," he delivers. The artist's swagger is on another level as he proceeds to go from broke over the pounding 808's. Cocky couplets like, "You show up to concerts looking like a fan / I pull up in car service looking like the man / Hella reefer smoke a lot of pictures being taken / My bitch from Atlanta my weed is Jamaican," will have you reaching for your rewind button with frequency, making "Cabin Fever" one of the defining songs on Wiz's loaded mixtape resume.

  • "Mezmorized"

    Wiz Khalifa

    The rhymer unleashed what would be one of the defining songs of his career in spring of 2010 in "Mezmorized," a potent cut included on his buzzworthy mixtape, Kush & Orange Juice. The track was Wiz at the height of his powers, spitting piffery over a hazy soundbed powered by synths and light snares provided by Cardo. After setting the scene with a little slick talk, he delves into the proceedings, spitting, "Uh, I don't love 'em, I don't chase 'em I duck 'em / Smoke something, go to a new state soon as I fuck 'em / Niggas be pressed for pussy, it ain't nothing / Instead of worrying about who that bitch fucking, why don't you get you some money." And the fact that he decided to open up what would be his magnum opus with this heater a testament to its undeniable appeal.

  • "In the Cut"

    Wiz Khalifa

    The main theme of Kush & Orange Juice may be getting lifted, but of all the songs included on the tape, "In the Cut" is arguably the best one dedicated to actually partaking in the act. Produced by Cardo, the track finds Wiz "in the cut, rolling doobies up," over a quirky beat that goes from frenetic to syrupy without notice. "Kush and orange juice be the components / Come to my crib see money so big you can't fold it, that's how I live / She poured her a lil gin, then rolled her another doob / Before she was finished, man, freaky Sheena got super loose," he serves. Wiz Khalifa inspires a new generation to roll up at the drop of dime.

  • "Never Been"

    Wiz Khalifa

    Trunks rattled and joints were rolled upon the arrival of Wiz Khalifa's track, "Never Been." Produced by Sledgren, the Kush & Orange Juice cut was an instant hit with listeners, and for good reason. Wiz saunters over the beat with finesse, spitting, "Empty bottles of Clicquot and ashes on the flo' / Towel under the do', we wasn't supposed to even smoke / I ain't tripping, never slip or slacking on my pimping Drop the nerds you with, come smoke a joint with he who's winning," and gives fans a glimpse into his playalistic lifestyle. "Never Been" rates high among young Khalifa's resume of bangers and is a sure-shot classic for those into dope flows and killer hooks.

  • "Black and Yellow"

    Wiz Khalifa

    Known for his relentless indie grind and having split ways with Warner Bros. Records in lieu of a proper release date for his album, Wiz shocked the rap game when he signed a new deal with Atlantic Records. Following the mass success of Kush & Orange Juice and decision to go back with a major, many were curious to see what the rapper's first move would be and found out when his Atlantic debut song, "Black and Yellow," touched down. Released in September of 2010, "Black and Yellow" would exceed expectations, becoming the official song for Wiz's hometown NFL team, the Pittsburgh Steelers and peaking atop the Billboard Hot 100, giving Wiz the first No. 1 single of his career. The track has since earned the status of being a modern-day classic and is one of the signature song's in Wiz's extensive catalog of fan favorites.

  • "Taylor Gang"

    Wiz Khalifa

    Fans of Wiz Khalifa got their own personal anthem when the rapper cooked up the song, "Taylor Gang," which was featured on his Cabin Fever mixtape. Produced by Lex Luger, the beat is powered by 808 drums, spooky synths and claps, over which Wiz does his bidding while bigging up his core fans. "You know I’m reppin’ Taylor / All my weed from Cali, so you know I’m smokin flavor / Ain't fuckin with blunts, you know we only smokin’ paper / And I throw it up so that you know just what my name is / Muthafuck a hater," he rhymes. The face of Pittsburgh gets melodic on the hook and details his rolling rituals and the love held for his clique. Lines like, "They let me in the club, fuck a dress code / Me and all my niggas rollin up the best smoke / OG kush from the westcoast / Oh you down to fuck? Well shorty, let's go," find an uber-confident Khalifa strutting all over the beat.

  • "Roll Up"

    Wiz Khalifa

    The Rolling Papers album was one of the most anticipated arrivals of Wiz's career -- he had pressure on him to deliver. And the rapper did just that with the album's second single, "Roll Up," which arrived at the top of 2011 and would quickly rise up the charts, peaking at No. 13 on the Billboard Hot 100. The song, which was produced by mega producer Stargate, was a sacharrine, puppy love anthem that ingratiated Wiz with soccer moms and the girl-next-door alike. Lyrics like, "It's your anniversary isn't it and your man ain't acting right / So you packin’ your Damier luggage up callin’ my cell phone, try and catch a flight / You know one thing straight, I’ll be there girl whenever you call me / When you at home that's your man, soon as you land you say that's all me," were full of Wiz's schoolboy charm and when matched with the sing-songy hook made "Roll Up" destined to be the record to solidify him as a crossover star.

  • "No Sleep"

    Wiz Khalifa

    "Last night I let the party get the best of me / Waking up in the morning: two hoes laying next to me / Plus I heard an officer arrested me / Good weed and cold drinks, that's the motherfucking recipe," Wiz Khalifa raps on the Rolling Papers single, "No Sleep." Produced by Big Jerm & Eric Dan, the production is upbeat, sunny and tailor-made for the Taylor Gang general to wax poetic about the joys of partying on the weekend. "No driving, no sleeping / Live it up like it's the weekend / When the DJ play the right song / Gonna drink, gonna party all night long," he delivers. Wiz Khalifa concocted yet another winner of a song, which went on to become his third biggest single to date.

  • "O.N.I.F.C"

    Wiz Khalifa

    After becoming the hottest rookie in hip-hop and releasing a successful major label debut, Wiz Khalifa's first move was to keep his foot on the gas and drop yet another mixtape. Taylor Allderdice arrived in 2012, a project featuring 17 tracks of original material. The effort was considered by many to be an upgrade from his previous offering, Rolling Papers. "O.N.I.F.C.," the tape's premier track, finds Wiz living and styling over an intoxicating beat, courtesy of Cardo and Sledgren. Swaying onto the track, Wiz goes in for the kill, spitting, "God damn, I'm rich as fuck, drunk as hell / Throwing money, pick it up, life is good, live it up / How much for that bottle, put it on my tab / Hop out like a model all them foreign tags / Get so drunk and high, I'll have to call a cab / You won't end up giving it back if you had this for one night." Devoid of a traditional hook, "O.N.I.F.C." is a weed-induced night on the town with Wiz in audio form and makes the grade as far as the rapper's finer material.

  • "The Race"

    Wiz Khalifa

    Introspection is all over Wiz's track "The Race," a riveting selection from Rolling Papers that finds the usually carefree rapper injecting a bit more substance into his material. "The world turning, the weed burning / Them haters talking, I keep earning / Know some who say life's a bitch, well I’ma keep flirting / And fuck that bitch for the money and Louis V purchases," he raps. Wiz reflects on his place in the game and the solitude that success can bring.

  • "Mary 3x"

    Wiz Khalifa

    Achieving mainstream success didn't deter Wiz Khalifa from servicing his devoted fans in between album releases, returning to the mixtape circuit in 2012 with his Taylor Allderdice project. Featuring some of the better music of Wiz's career, Taylor Allderdice was rated higher than his debut album by many fans and one of the reasons was the high-powered selection, "Mary 3x." Co-produced by Cardo and Sledgren, the beat is a hypnotic soundscape over which Khalifa maneuvers effortlessly. "And you could sit right on your ass, doubting / While I'm somewhere rolling up grass, going up where the clouds is / Some niggas say they get so high that I ain't fucking wit' em' / I say if them niggas got that high, man, I ain't fucking wit' 'em," he rhymes, before professing his love for the Mary Jane on the hook. In a catalog with innumerable references to the sticky, "Mary 3x" is superior to many and remains a toker's favorite.

  • "Work Hard, Play Hard"

    Wiz Khalifa

    The rapper may be perceived as a carefree stoner, but contrary to popular belief, he's all about his business first and foremost. "Work Hard, Play Hard," the lead single from his O.N.I.F.C., Wiz's fourth studio album, proves just that. The indie rock star-turned-major label cash cow makes it known that the spoils have not tempered his work ethic a bit. "Diamonds all on my ring nigga / Gold watches, gold chain nigga / Hundred thou' on champagne nigga / Yeah my money insane nigga," he delivers. Wiz is in full stunt mode and reveling in his riches acquired. The motivational hook became an anthem and modicum for hard work and determination and earned Wiz another platinum single, further marking his ascension into the upper echelon of pop stars.

  • "We Dem Boyz"

    Wiz Khalifa

    Ominous drums announced Wiz's return in 2014, in the form of "We Dem Boyz," the lead single to his fifth studio album, Blacc Hollywood. Produced by Detail, the beat is powered by crushing percussion, crashing cymbals and subtle piano keys, over which Wiz holds court while dropping bombastic boasts. "Pussy must be serious / Scared of heights come face your fears / Do it just like Nicki gon' and bend it over / Say she never smoked I turned her to a stoner," he raps. Wiz is devoid of fucks to give on "We Dem Boyz" and prefers to grandstand with a lot of weed, women, and alcohol on this outing instead, making for a hell of a record to turn up to.

  • "See You Again"

    Wiz Khalifa

    "It's been a long day without you, my friend / And I'll tell you all about it when I see you again / We've come a long way from where we began / Oh, I'll tell you all about it when I see you again," Charlie Puth croons on "See You Again," his somber collaboration with Wiz Khalifa. This song would make an impact far beyond anything either artists could dream of. Recorded in the memory of deceased actor, Paul Walker (of The Fast and the Furious fame), the record was dedicated to bittersweet memories and coming to terms with saying goodbye to a loved one. Wiz's raps are as poetic and genuine as they come. "Damn, who knew / All the planes we flew, good things we been through / That I'd be standing right here talking to you / 'Bout another path I know we loved to hit the road and laugh / But something told me that it wouldn't last," he spits on the song's opening verse while channeling the feelings of love and friendship lost into song. "See You Again" would become the biggest hit of Wiz Khalifa's career, spending 12 weeks atop the Billboard charts and earning three Grammy nominations, in addition to international acclaim.

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