The Cool Kids’ second studio album, Special Edition Grandmaster Deluxe, doesn’t start with a bang, but a cough. The first voice listeners hear on “The Moonlanding” is Chicago comedian Hannibal Buress, who wryly comments, “Not the lukewarm kids, not the hot kids, not the tepid kids, not the warm kids, The Cool Kids, back at it again.” It works because the Chicago duo are in on the joke. For the past five years, the group was ice cold, despite a strong contingent of fans longing for their return. With Special Edition Grandmaster Deluxe, Chuck Inglish and Sir Michael Rocks are re-entering the musical landscape as grizzled veterans.

Chuck’s braggadocious statement on the first verse of the album, “We call it Shark Week cause you niggas is some biters,” is partially true. While The Cool Kids didn’t invent nostalgia, in 2007 they were among the first crop of internet rappers to expertly market the ’80s using slick rhymes, a Myspace account, and outfits ripped from the pages of Word Up! magazine. On one of their first viral hits “88,” they expertly sold this image, rapping:

I’m on my ’88 shit

Cuban link chains and Cazal frame lenses

Guess Jeans, stone-washed

Along with rappers like Wale, Kid Cudi, Charles Hamilton, XV, Donnis, and Blu, The Cool Kids embraced the chaotic upheaval of the Internet. With the help of emerging social platforms like Myspace and hip-hop blogs, musicians could bypass the gatekeepers of yore—A&Rs, journalists, tastemakers, and DJs—and upload their music directly to the masses outside of the major label system. The first generation of rap artists championed by the Internet of the late aughts is still dealing with the effects of being the first to test the outer limits of the Internet as a marketing tool.

Before hip-hop and R&B were officially the most popular music genre, it was going through the same growing pains as the rest of the music industry in a post-Napster landscape. Ten years ago, enterprising men and women knew that there was untapped potential in the MP3 economy. The embrace of new technology runs through rap’s roots, and so sites like NahRight, 2DopeBoyz, and OnSmash came to fill this technological and cultural void. Rap fans—who had grown accustomed to the mixtape culture of cities like New York, Atlanta, and Houston—gravitated to this new ecosystem that laid the groundwork for hip-hop’s surge in popularity once streaming made those stats legit.

Back then, this relationship presented a dilemma. How would rappers entering the churn of the emerging blog cycle transition their Internet hype into real-world success? To reminisce about the peak of the blog era is to fondly remember a time of Saigon Entourage cameos and million dollar Interscope deals for the Sonic the Hedgehog-obsessed Charles Hamilton. The blog posts during this time were short, direct, and built upon the small, but bubbling culture coalescing around the rappers and writers making a new space.

In the mid-to-late 2000s, the release schedule for rap music more than any other genre was a deluge of unfettered singles, mixtapes, and remixes. Listening, managing, and promoting each rap release and creating a central hub for this burgeoning digital scene became a full-time job in and of itself. In some ways, these blogs introduced hip-hop fans to the first kernel of what streaming would eventually become.

In 2017, the curation of hip-hop has transitioned away from blogs to streaming platforms like Spotify and SoundCloud. A music programming veteran for places MTV and BET in the past, Tuma Basa now runs RapCaviar—Spotify’s flagship playlist. As the global programming head of hip-hop at Spotify, Tuma’s mixture of analytics-driven curation combined with gut instinct is an extension of what Eskay of NahRight or Meka of 2Dopeboyz were accomplishing 10 years ago. The major difference is the absence of words and the 7.7 million followers devouring Rap Caviar as a playlist.

In 2007, then-presidential hopeful Barack Obama had The Cool Kids play a fundraiser and told them, "You're up-and-coming like me, that's good!"

Would today’s rappers like Lil Uzi Vert—who rode the wave of Spotify playlists all the way to a No. 1 rap record—succeed in the same manner a decade ago? Vert’s nostalgia mines the 2000s—Marilyn Manson, Paramore melodies, Scott Pilgrim cover art—in a similar way to how The Cool Kids worshipped the ’80s. “XO TOUR Llif3” sounds as niche now as a song about BMX bikes did a decade ago. But the streams it generates count toward his album sales, unlike the page views and streams “Black Mags” may have generated on NahRight.

Tracks like “Black Mags” were viral in a time when the term still felt genuine and partially true. Whether it was the iconic black-and-white video or the duo’s Rhapsody commercial, “Black Mags” seemed organically grown. Fans wanted an album from the group when in reality judging their success by an album was beside the point. Chuck and Mikey were always better at making songs that grew into moments, instead of large career-defining bodies of work.

The duo did release a debut studio album though, 2011’s When Fish Ride Bicycles. But it dropped two years after Chuck Inglish claimed it was nearly done. It got decent reviews but was mostly filled with songs they had previously released on mixtapes. By that time, their buzz had considerably declined and they were no longer at the epicenter of internet rap culture. Hip-hop’s attention shifted away from the blogs and onto Twitter, and a new batch of rappers like A$AP Rocky and Kendrick Lamar were viewed as the future. Meanwhile, The Cool Kids ended up splitting. But, as Chuck Inglish recently explained on the No Jumper podcast, it wasn’t over personal differences:

The business situation was fucked from the jump, we just ran out of energy to deal with the shit….It wasn’t about the label. It was about what the paperwork said as far as us not giving them another option because we didn’t believe it. We checked our paperwork and it was fucked. We believed in someone we trusted, then the motherfucker pulled some shit on us. So it was like, let’s stand our ground… I’m not about to give your bitch ass an album, I’m trying to fight you.

The record business has always been shady, but would The Cool Kids have been regulated to the same fate today? In a Vulture feature about the rise of RapCaviar, Lyor Cohen—the global head of music for YouTube—discussed the changing nature of music consumption in 2017. “Hip-hop artists have liberated themselves from the shackles of the album,” said Cohen. “The album is far less important than just putting out music.” The idea that the album is no longer the ultimate sign of success is something Inglish and Rocks could have benefited from. But they never did, because the music industry had yet to figure out how to adapt to their pioneering albeit scattershot road to success.

The Cool Kids’ second album is a solid effort. The beats are still filled with fat bass and hard kicks, while the lyrics are warmly nostalgic. Where Special Edition Grandmaster Deluxe succeeds the most is positioning Chuck and Mikey as more refined versions of what they gave fans a decade ago.

Unfortunately, it’s 2017 and blogs no longer make or break artists. The Cool Kids may be the victims of a changing musical landscape—stymied by the trappings of a bygone era that never allowed them to fully reap the fruits of their labor—but they’re also the blog rappers that walked so that Spotify and SoundCloud rappers could fly.