Why one of hip-hop’s longest-standing annual traditions is ending

After 20 years, Skillz is bringing his iconic year-end “Rap Up” series to a close.

NEW ORLEANS - JULY 08: Rapper Skillz perform  at House of Blues on July 8, 2009 in New Orleans, Loui...
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ByJayson Buford
Originally Published: 

Skillz’s “Rap-Up” is the closest thing to an annual tradition hip-hop has. For the past 20 years, every January, Skillz has given a lyrical recap of everything that mattered in the previous 12 months. He's announced that this year’s edition, about everything that transpired in 2021, will be the last edition of the series. “The Rap-Up” is time-sensitive. There’s a 2000’s bubblegum-pop in it, and at its earliest, a recounting of the news when it wasn’t happening so quickly. The 2000s were when MTV videos had all the eyes of the planet watching them, and we learned about artists through Vh1’s Behind the Music, not through their YouTube documentaries. “The Rap-Up” series, along with BET’s Rap City, exists as nostalgia and something foreign. They’re different programs, with Rap City being a showcase for rappers to interview and spit freestyles and “The Rap-Up” being more singular and only belonging to Skillz. But they both represent a time in hip-hop where pop culture was at its stickiest and the stakes weren’t too high, but it still mattered and inspired.

In the inaugural 2002 edition, Skillz hilariously adopted Common’s “Come Close” and riffed on Eminem becoming Elvis, made fun of Justin Timberlake’s attempts to make "Black music," and joked that the then- and now couple Jennifer Lopez and Ben Affleck would break up by the time the song ended. In other years, he chronicled everything from Mel Gibson’s anti-Semitic rants to LeBron James’ decision to leave the Cleveland Cavaliers to play with the Miami Heat, from the historic election of President Barack Obama to Kobe Bryant’s hilariously awkward “white-hot” photoshoot with the LA Times. If you remember it happening in pop culture in the past 20 years (and, honestly, even if you don’t remember), Skillz has had a “Rap-Up” reference to it that had us share the memory.

Skillz entered the music industry as a more conventional rapper, working alongside fellow Virginians like Missy Elliott, Timbaland, and The Neptunes while earning his stripes (and paychecks) behind the scenes as a writer for other rappers. (He chronicles the latter on “Ghostwriter,” his 2000 song where he comes at the shady business practices of the industry while boasting about how he’s written for listeners’ unnamed favs.) His 1995 LP From Where??? is a workmanlike underground record, with sounds from seminal producers like J. Dilla and DJ Clark Kent, and many of his other albums do comparatively traditional hip-hop very well, with thoughtful, clever lyrics. He initially created the “Rap-Up” series as a novelty, an add-on treat for his mixtapes. But they quickly took on a life of their own — and that’s something that took getting used to for him.

"As a competitive rapper, I was thinking ‘why is this the one catching on? I have way more harder stuff than this,’” Skillz, 47, tells Mic. “People kept asking me for another track, and I was thinking, ‘Oh, they want another one of those.’ Then, one day my man from Virginia called me and said, ‘mad people downloading the song,’ that he needs more bandwidth because ‘I get way more traffic from my site than expected.’"

Twenty years is a long time, and revisiting the “Rap Up” installments allow us to see how we — as a hip-hop community, and the country as a whole — have grown. There may be nostalgia when you hear Skillz joke about Best of Both Worlds, Jay-Z’s misguided collaborative album with R. Kelly, but working with a sexual predator wouldn't fly now. The political stratosphere went from being able to be riffed on comedically to the news itself becoming like SNL or Veep, with satire blurring into real-life. As the real world became more difficult to live in, wrapping up the year felt like more of a somber occasion than the lighthearted, silly vibe that defined the series. Headlines got more dystopian, laughs were harder to find, and imagination began to run dry.

"I wanted to end at 20 years. You can’t end it at 19 years. But also, it wasn’t any way to make this fun anymore,” Skillz said. “Last year, I had to talk about Kobe, COVID, and George Floyd. I’m a Black man in America. I won’t say I’m used to bad news, but I have had to deal with things because the system is what it was. Times are different but things are still the same."

It's best to approach the “Rap Up” series as a collective response to how Americans process the culture around them. And as much of pop culture, Black Twitter is a comparable compass. On Black Twitter, everything is processed at the breakneck speed of trending topics and with undying sardonic humor. Skillz’s “Rap-Up” series takes a similar approach: it slyly condenses 12 months of headlines into six minutes of jokes and hot takes, with the pace of a timeline scrolling down your screen. In ‘05, he rapped about the Stop Snitchin campaign in a dubious tone: "I told y’all I saw a 7-year-old with a Stop Snitchin shirt on/I’m like who snitched on you, your kindergarten teacher?" It was classic Skillz, recapping what was going on in Black culture with an earnest sense of humor. The series played like a one-man conversation at the barbershop, like someone telling the gossip that happened in culture while you get your cut from your OG.

In the Trump era, Skillz was more somber and his tone more intense. As police violence videos became front and center in the American discourse, Trump’s rhetoric became inescapable, and Skillz spoke up. He ended “2016 Rap Up” with a long sermon-like rap over what transpired in the presidential election, wondering where we went wrong since the Obama era (there’s some false hope in that, but Skillz isn’t a politics professor). The “2020 Rap-Up”— cleverly subtitled “Throw It In The Trash” — took on a similarly somber tone, with the COVID-19 pandemic, Kobe Bryant’s death, and other tragedies taking their toll on Skillz just as much as they did on us. This year was similarly rough, as the pandemic continued and hip-hop suffered from the murders of Drakeo the Ruler and Young Dolph and the causal bigotry of Lil Boosie and DaBaby.

Still, Skillz has ultimately had fun doing this. His 20-year run of Rap Ups have culminated in further respect from music industry peers and from fans who have embraced the songs as a way to come closer together. That confusion from the early years of the series has grown into gratitude.

"To have something that people want from you in hip-hop at my age was something significant for me,” Skillz said. “Questlove was a big supporter of them early. He and Young Guru [Jay-Z’s engineer] would tell me, ‘this is huge for the culture, you have to continue them.’ It’s a tradition. A guy once told me, ‘I pick my son up from Pennsylvania, and our tradition is that we listen to the Rap-Up in the car. We’ve been doing that since he was 7 years old.’ It has become a part of people’s lives."