To celebrate XXL's 150th issue, here's a look back at the 150 most important people, places and things in hip-hop over the last 16 years. The list covers artists, events, labels, execs, fashion, beef, lifestyle and more. You can pick up the magazine on newsstands or download the digital version for the full scoop on who and what made the list and why.

Compiled by Dan Buyanovsky, Eric Diep, Kathy Iandoli, Sowmya Krishnamurthy, Amy Linden, Dan Rys, B.J. Steiner, Tzvi Twersky and Jeff Weiss

Artists

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> Jay Z (pg. 56) -

“M.J. at Summer Jam, Obama on the text/Y’all should be afraid of what I’m gon’ do next,” Jay Z boastfully warned on 2009’s “On To The Next One.” And he was right. Who else on Earth — let alone within hip-hop — had the pull to bring out Michael Jackson at rap’s biggest event, as he did in 2001, and grow to be buddies with the current president of the United States a decade later. ''He’s always had that 'it' factor,'' says industry vet Kevin Liles, who has known the Brooklyn native since the early 1990s. “Jay pushes boundaries—not just to be different but to inspire the culture and dream bigger.”

It took years of empire-building for Hov to position himself as the most lionized entity in hip-hop—and maybe all of music—but there’s no doubt that that’s what he’s become since dropping his debut album in 1996. He’s combined the verbal precision of The Notorious B.I.G., the business acumen of Jimmy Iovine, the spokesmanship of Russell Simmons and the dreams and ambitions of every kid across America to position himself as rap’s most beloved and emulated figure.

And after countless hits and verses, 13 No. 1 albums, founding Roc-A-Fella and Roc Nation, multiple endorsements and deals, Hov is proving he’s still got it. “Jay’s lasting legacy is his ability to evolve,” Liles says. “To always bet on himself and continue to propel his reach while maintaining relevancy.”

New rules.

> Snoop Dogg (pg. 56)
> The RZA (pg. 57)
> Pharrell (pg. 57)
> Dr. Dre (pg. 58)
> Eminem (pg. 59)
> Rick Ross (pg. 60)
> 50 Cent (pg. 62)

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> Nelly (pg. 62)

There was a time when Nelly was the hottest rapper out. The St. Louis-native signed to Universal Records then dropped his debut album, Country Grammar, in 2000 and went nine-times platinum. The LP featured four smash hit singles including “Country Grammar (Hot Shit),” “Batter Up,” “E.I.” and “Ride Wit Me.” Two years later the lady-friendly rhymeslinger dropped Nellyville, which sold six million copie.  Another two years later, Nelly Nell accomplished an even bigger feat with the release of his third album, Sweat/Suit. The effort, which came out as two separate discs, sold four million copies collectively. Sure, the second leg of his career faltered a bit, but Nelly made his impact bringing fun hip-hop to heads across the land.

> Funkmaster Flex (pg. 62)
> Kanye West (pg. 64)
> Big Pun (pg. 64)
> Lil Wayne (pg. 66)
> Nas (pg. 66)
> The Diplomats (pg. 66)
> Lil Kim (pg. 66)
> Missy Elliott (pg. 67)
> Mary J. Blige (pg. 68)
> Tupac (pg. 69)

The late great 2Pac was known for being a combination of pensive and reckless. Both of those attributes individually inspired generations of rappers after him. “He influenced a lot of artists posthumously,” radio/TV host Sway Calloway explains. “After his death and even before his death, the way he rapped—his diction and the emphasis he placed on words—the different ways that he delivered his lyrics, that you heard a lot in Master P and a lot of No Limit artists. Just guys who came from a street background—’Pac was a muse for them.” 2Pac allowed hip-hop to speak up by any means necessary. He defended himself, even if he was wrong. That boldness is still felt today through other artists after him, along with his own extensive posthumous catalog. Since his death in 1996 ’Pac’s estate has released seven albums that include unreleased 2Pac material that have gone 16-times platinum collectively. There have also been two live albums, five compilations and two remix LPs plus one soundtrack. In death he has been able to influence new generations of MCs with this music and his untimely passing that has become a cautionary tale about beef taken to the extreme. “The things he would say could lead to a riot if he wanted them to,” Sway continues. “I think 2Pac taught a lot of artists how to take their anger and their emotions and articulate them.”

> R. Kelly (pg. 69)
> DJ Drama & Gangsta Grillz (pg. 70)
> Biggie (pg. 72)
> Timbaland (pg. 72)
> Drake (pg. 72)
> Swizz Beatz (pg. 72)
> ?uestlove (pg. 74)
> Mos Def (pg. 74)
> Foxy Brown (pg. 76)
> OutKast (pg. 76)
> T.I. (pg. 76)
> Nicki Minaj (pg. 78)
> Sean "Diddy" Combs (pg. 81)
> Young Jeezy (pg. 81)
> Common (pg. 81)

Labels
> Interscope Records (pg. 56)
> Def Jam Recordings (pg. 57)
> Sony/Columbia/BMG (pg. 59)
> End Of Rawkus Records (pg. 60)

When Rawkus Records shut its doors in 2007, it signified more than just another indie label going belly up. It was the end of an era and a movement that Rawkus helped to nurture and promote since it began in 1996. The NYC-based Rawkus was a hip HQ for (mostly) East Coast rappers that included Hi-Tek, Pharoahe Monch, Talib Kweli and Mos Def, both solo and as the group Black Star. Artists frequently collaborated with each other, and while the overall vibe was noncommercial, smart and progressive, Rawkus was never soft.

> Ruff Ryders (pg. 61)
> Atlantic Records (pg. 62)
> Universal Music Group (pg. 64)
> Cash Money Records (pg. 64)
> No Limit (pg. 69)
> Epic (pg. 70)
> Warner Music Group (pg. 80)
> Koch Records (pg. 80)
> EMI/Priority/Capitol (pg. 81)
> Murder Inc. (pg. 81)

Music

Nas Hip Hop Is Dead
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> "Hip Hop Is Dead" (pg. 56)

Hip-hop was in a precarious spot in 2006—D4L’s snap-happy “Laffy Taffy” hit No. 1 on the Billboard Hot 100, for goodness sake. Hip-hop wasn’t quite “dead,” but it was as a response to this fleeting moment that Nas announced, in May 2006, the title of his eighth studio album would be Hip Hop Is Dead, which ended up hitting stores that December. The bold proclamation gave rise to endless debate—old heads versus the new school, Southern stars versus the New York establishment, one online commenter versus another.

> Jay Z's Retirement (pg. 58)
> Eminem & Elton John Perform Together (pg. 60)
> Eminem & Jay Z Perform At Yankee Stadium (pg. 61)
> Hyphy Music (pg. 67)
> DMX Gets Two No. 1 Albums (pg. 67)
> good kid, m.A.A.d. city (pg. 68)
> Backpack Rap (pg. 69)
> Jay Headlines England's Glastonbury Festival 2008 (pg. 69)
> Chopped & Screwed (pg. 70)
> The Legend Of Dr. Dre's Detox (pg. 72)
> Mixtapes (pg. 76)

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While hip-hop mixtapes date back to the 1970s, they hit an all-time high in popularity in the early 2000s, helping artists such as 50 Cent and his G-Unit crew, T.I., The Diplomats and many other rappers both signed and unsigned get their music to the streets via DJ-helmed compilations and later their own self-made discs. The music on the tape could’ve been rare, never-heard verses, album outtakes, new original songs or even remakes of other artists’ songs. Often the tapes would act as a platform for rappers to get new music heard or maybe even diss a competitor. The tapes frequently included crazy skits or artists speaking recklessly. “Mixtapes were like radio for the streets,” says the West Coast’s DJ Skee. “It was a way to break artists and records early.”

In the mid-2000s with the rise of the Internet and MP3s, there was a birth of online download communities such as datpiff.com, djbooth.net and livemixtapes.com that began offering mixtapes on their sites. Traditionally up until that point the tapes were sold by vendors in the hoods and out of car trunks across America. Skee explains, “With the Internet and blogs, they’ve replaced [street mixtapes] in terms of music discovery because you don’t have to wait for somebody else to put together a compilation.” He continues, “When an artist puts something out now, you can go out there and find it.”

By late 2000s mixtapes became less of a promo tool and more like an album. By the time Drake came along in 2009 with his breakout mixtape So Far Gone—a mixtape in name only—he changed the game again, likening the mixtape to a digitally released demo of sorts. More recently, mixtapes have served as jumping-off points for new artists like A$AP Rocky and Chance The Rapper, who found avid supporters via viral projects. Long live the mixtape.

> Trap Music (pg. 76)
> The Miseducation Of Lauryn Hill (pg. 78)
> Crunk Music (pg. 80)
> Three 6 Mafia Wins The Academy Award For Best Original Song In 2006 (pg. 81)

Execs
> Julie Greenwald (pg. 57)
> Kevin Liles (pg. 62)
> Chris Lighty (pg. 64)
> L.A. Reid (pg. 67)

L.A. Reid has become one of the most successful music executives in hip-hop. Noted for signing and developing such acts as OutKast and TLC early in his career, L.A. was also the CEO of the Island Def Jam Music Group from 2004 to 2011, helping make the label a roaring success by building a broader roster with shrewd signings while developing stars like Kanye, Rihanna and Justin Bieber. Now Reid's the chairman of Epic Records and signed new sensation Future.

> Hype Williams (pg. 68)
> Lyor Cohen (pg. 70)
> Russell Simmons (pg. 78)
> Jimmy Iovine (pg. 80)

Locales
> California (pg. 56)
> New York (pg. 58)
> Atlanta (pg. 60)
> New Orleans (pg. 61)
> Miami (pg. 74)
> Houston (pg. 80)
> Hollywood (pg. 80)


Tech

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> Auto-Tune (pg. 56)

T-Pain made a career out of it. Kanye West made an album using it. Lil Wayne had the biggest hit of his career with it. Jay Z deaded it (or tried to). Auto-Tune has been a divisive and prevalent mechanism within hip-hop song-making for the last half-decade plus, but it doesn’t seem to be going anywhere. It has both created and been unable to sustain one-hit wonders and also given those rappers otherwise unable to carry a tune the confidence to think they can do so. Though it’s not as popular as it was in 2008, today, Future and Chief Keef are making sure the trend, albeit with slightly different technology, is alive and breathing.

> Beats By Dre (pg. 56)
> The Internet (pg. 57)
> MP3s (pg. 60)
> Ringtones (pg. 60)
> Fruity Loops (pg. 61)
> Social Networking (pg. 67)
> YouTube (pg. 68)
> Pro Tools (pg. 74)
> Smartphones (pg. 74)

Fashion
> Timberlands (pg. 56)
> Designer Labels (pg. 58)
> Fitted Hats (pg. 58)
> Jewelry (pg. 59)
> FUBU (pg. 59)
> Jordan Brand (pg. 61)
> Nike (pg. 64)
> Grillz (pg. 69)
> Rappers' Clothing Lines (pg. 69)

Rappers have been name-dropping brand-name clothing since the invention of the genre, the late 1990s kicked off a growing trend of rappers starting their own clothing lines, with Diddy’s Sean John and Jay Z’s Rocawear leading the way before 50 Cent’s G-Unit line broke through in 2003, with just about every major rapper following suit. The trend faded a bit after that, but hip-hop’s continued emphasis on style and fashion has led to a rebirth of late, with Lil Wayne’s Trukfit line hitting stores in 2012 and Kanye’s APC collection debuting this past summer.

> Reebok (pg. 74)

Lifestyle
> Slang (pg. 58)
> Marijuana (pg. 59)
> Obama (pg. 59)
> Tattoos (pg. 60)
> Sports (pg. 66)
> Cadillac Escalade (pg. 70)
> Strip Clubs (pg. 70)
> Liquor (pg. 72)
> Stop Snitching (pg. 74)
> Video Girls (pg. 78)
> Cliques/Crews (pg. 80)


Beefs, Deaths & Legal Entanglements
While > Beef (pg. 66) in general made the list, there were some specific beefs that fought their way onto the list.

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> Hip-Hop Peace Summit (pg. 57)

In the immediate aftermath of the deaths of 2Pac and Biggie, rap music found itself reeling from the tragic consequences of unchecked beef. On April 11, 1997, hip-hop's elite decided to act, and Minister Louis Farrakhan called a meeting in Chicago to broker peace. Stars such as Goodie Mob, Snoop Dogg, Too $hort and Chuck D were in attendance while Common and Ice Cube hugged on stage, ending their feud. Meanwhile, a symbolic truce was called between warring factions of East and West, officially marking the end of their bloody feud.

> Death Of ODB (pg. 59)
> T.I.'s Legal Drama (pg. 59)
> Canibus/LL Cool J Battle (pg. 61)
> Taylor Swift Vs. Kanye West (pg. 62)
> Nas Vs. Jay Z (pg. 62)
> The Breakup Of Dame Dash & Jay Z (pg. 66)
> 50 Cent Vs. Kanye West (pg. 66)

Beef ain’t new to hip-hop. But the 2007 battle between Kanye West and 50 Cent was something else. With 50 and ’Ye each dropping their third albums on the same day (Curtis and Graduation respectively), 50 declared that if Kanye’s first week sales bested his own, 50 would retire. The threat made for great press, but when the numbers came in, Kanye won, with Graduation selling over 950,000 copies to Curtis’ 690,000-plus. Of course 50 didn’t quit, but he never regained his footing as the balance of power shifted away from club bangers.

> The Source Vs. Eminem (pg. 67)
> Hot 97 Shooting (pg. 67)
> The Death Of Jam Master Jay (pg. 67)
> Nas & Jay Z Squash Beef (pg. 68)
> The Club New York Shooting (pg. 68)
> Hip-Hop Tax Troubles (pg. 69)
> The Breakup Of The Hot Boys (pg. 70)
> The Death Of Mac Dre (pg. 70)

Mac Dre was something close to a folk hero to the hyphy heads in the Nation Of Thizzlam. In the late 1990s, Mac was the Bay’s answer to Pimp C, a swaggering, boastful everyman who helped to pioneer the area’s signature sound until his tragic, unsolved murder on November 1, 2004. Dre might have been slain as the hyphy movement started to buzz nationally, but it’s a testament to his influence that almost a decade after his death, homage is still paid to this fallen star.

> 50 Cent Vs. Murder Inc. (pg. 72)
> Kanye Vs. George Bush (pg. 76)
> DJ Drama Raided By The Feds (pg. 78)
> Rick Ross Outed As C.O. (pg. 78)
> 50 Cent Vs. Rick Ross (pg. 80)

Media
> Hot 97 (pg. 57)
> 8 Mile (pg. 57)
> Rapper Reality Shows (pg. 58)
> 106 & Park (pg. 60)
> MTV (pg. 78)
> BET (pg. 81)

Business
> Lawyers (pg. 58)
> Recession Of 2009 (pg. 61)
> Bootlegs & Leaks (pg. 61)
> SoundScan (pg. 62)
> 360 Deals (pg. 64)

Once music piracy ran rampant, a label deal based on the strength of music sales became archaic. 360 deals arrived, where entertainment entities would front costs for creating an artist’s project in exchange for ample creative control and a percentage of an artist’s career, namely touring. The first documented 360 deal happened in 2002 with U.K. pop star Robbie Williams, but the trend became popular in hip-hop in 2006, mostly with the rising sales of ringtones. Jay Z changed the face of 360 deals in 2008 when he inked one with Live Nation for $100 million-plus. But that’s just Jay.

> Jay Z Buys The Nets And Brings Them To Brooklyn (pg. 64)
> 50 Cent Sells Vitamin Water (pg. 68)
> Jay Z & Beyonce (pg. 72)
> Hip Hop Since 1978 (pg. 74)

The name Hip-Hop Since 1978 may not ring bells to the average music fan, but when an employee from hip-hop’s most all-mighty management company calls, the ring is immediately answered. Founded by former Roc-A-Fella executives Gee Roberson and Kyambo Joshua in 1998, the New York agency originally called Roc Da World currently shepherds the careers of Lil Wayne, Kanye West, Nicki Minaj, Young Jeezy, T.I. and Drake. Later re-christened after Joshua’s “Hip Hop” nickname and year of birth, the 2011 addition of Young Money “Chief Visionary Officer,” Cortez Bryant, turned the company into rap’s William Morris. All of the partners double as music executives, A&Rs, and film and television producers. How can one firm have all that power?

> Rappers Sell 1 Million Records In Their First Week (pg. 76)
> Sponsorships (pg. 76)
> Jay Z Becomes Def Jam Recordings President (pg. 78)