Almost exactly five years after playing the Bud Light Stage at Lollapalooza and giving what’s probably among the better performances I ever seen at Lollapalooza, Childish Gambino is back and now for the first time not only a headliner for the upcoming 2019 edition of the world-renowned music festival, which takes place in Chicago’s famed Grant Park. But he’s also now one of the biggest artists in all of the world. One of upwards of 14 acts (which maybe a record number of returning acts), who are returning for the second or even third time in 8 years to the Lolla stage. Also joining Gambino for the third time at Grant Park in that time frame in a couple of weeks is Twenty One Pilots, Fitz and the Tantrums, Tame Impala, Flume and Gary Clark Jr. While acts such as The Chainsmokers, Flume, Hozier, Rüfüs Du Sol, Maggie Rogers, RL Grime, 6LACK, Arkells and Chicago’s very own Saba will all be returning to Lollapalooza for the second time in five years. With only a couple of weeks till the gates at Grant Park open and all the madness insues, the speculation really starts to begin on who can be brought out as special surprise guests like there has been throughout the years too.
Looking at this year’s lineup, this is one year where you may see several surprise guests, pop up during that first weekend in August and a few of those guests for one, two, three or even more different sets during that time. Three of the main names I wouldn’t be surprised not only popping up, but for several different sets throughout that weekend is, J. Cole, Rick Ross and Ty Dolla $ign. Homegrown Chicago hero, Chance the Rapper, who despite not being on the lineup, there’s always a chance of him popping up as a surprise guest in his hometown. Giving his history of being at three of the last five Lollapalooza’s, whether he was on the actual lineup or not, you know that’s always a possibility and with his recent announcement that his highly-anticipated debut album, The Big Day, is set to release in a little over a week on July 26th, it gives Chance even more incentive to crash the annual four-day world-renowned Summer festival at the famed Grant Park in his hometown. His connection to several other artists performing that he has previously collaborated with like Lil Wayne and fellow homegrown Chicago product Saba, being on the lineup also make it a very strong possibility. Especially given that his biggest record to date is still the Wayne featured smash hit, No Problem, what better way to crash Lolla then seeing Weezy bringing Chance out in front of his hometown crowd when he perforrms his set on the T-Mobile stage that Saturday evening. Which would absolutely make the crowd go bonkers. I could also possibly see Francis and the Lights returning the favor by bringing Chance out during their Sunday afternoon set in much the same way he brought them out during his very memorable headlining set at Lolla just a couple of years ago too.
Moving back to Cole, Ross and Ty., one or all three have collaborated with several of the rappers set to perform that weekend. So I wouldn’t be at all surprised to see somebody like Cole coming out as a surprise guest during his Dreamville Records artist J.I.D’s set on that Sunday afternoon for the final day of the festival or even during 21 Savage’s and 6LACK’s sets to perform his guest verses on the records of those respective artists singles he’s featured on. While I also wouldn’t be to surprised to see Ross and Ty both possibly brought out during Wayne’s set that Saturday night of the festival and Meek’s set that Sunday night on the final day of the festival. Given all of those artists history together with collaborating together it would make perfect sense, but at the same time I also wouldn’t be surprised if they didn’t either. I think it’s really dependent more so on Wayne and Mill, if they decide to bring several guest surprises or just one or surprisingly not any during their sets on whether it turns into a Lollapalooza weekend known for several high-profile guests brought out on stage that weekend.
You know it’s almost a given that Victoria Monét will be brought out by Ariana Grande during her headlining set to close out the festival that Sunday and that Chicago’s own Saba will likely have most, if not all his Pivot Gang crew with him during his performance on the first day of the festival that Thursday evening. Especially given that they just dropped their debut album, You Can’t Sit With Us, just this past April. A few more smaller names I also wouldn’t be to surprised to see pop up as guests during the festival is perhaps even Chicago’s very own Jean Deaux and Valee, who have both collaborated with Saba and Smino.
If Lollapalooza festival-goer are expecting any more surprise guests throughout that first four-day weekend of August, I unfortunately don’t see too much more really being a possibility though outside of that. Unless they are of the big cross-performance variety of other performers bringing out performers already scheduled to perform at Lolla. Which honesty probably more often times than not happens more than performers bringing out special surprise performers that aren’t on the lineup at all. The biggest possibilities of such performances happening being that Thursday, Aug. 1st and Saturday, Aug. 3rd of Lolla, when H.E.R. could possibly bring out YBN Cordae, Lil Baby could possibly bring out Gunna, 6LACK can be brought out by Normani and even Smino brought out by Saba. With 6LACK, Saba and Smino also a possibility of being brought out by J.I.D. for his solo set on that final day of the festival on Sunday, Aug. 4th and/or J.I.D. being brought out by 6LACK for his own solo set on that Saturday, Aug. 3rd. That Friday, Aug. 2nd of the festival could also possibly see anyone from Meek Mill, Lil Baby and/or Gunna as possible guest performers brought out by 21 Savage. While that final day of the festival on Sunday Aug. 4th, there’s even a possibility of Meek bringing out 21 during his own solo set, as well as his own recently signed to his Dream Chasers Records label back in March artist Calboy. The latter a homegrown Chicago product and one of just two Chicago acts on this year’s lineup.
Whether they happen, big name or even small name guest surprises, or maybe even none at all. I think this is honestly, though not as great as some of the very stellar lineups of year’s past, still a pretty decent lineup and not as bad as a lot of people are really making it. There should as there’s every year still be some really amazing performances scheduled to perform such as Janelle Monáe, Childish Gambino, H.E.R., J.I.D. and Gary Clark Jr., among others that will definitely make it worth being there.