Lollapalooza 2024 Preview

Let the speculation begin. Most every year there is at least a few artists that bring out special guests ranging from big names to not so big names during Lollapalooza here in Chicago. With speculation from the very moment the lineup is revealed to what possible special guest artists will be brought out by the headliners, as well as the other performers during the four-day festival.

With Lollapalooza celebrating its 20th anniversary here in Chicago this year. There maybe a little more incentive for artists to bring out guest performer’s even more so than usual too. Which is something that though it’s somewhat common. It is not as common as when other festivals like Coachella have several big name surprise guests almost every year. So it will be interesting to see what artists of this year’s performer’s that ranges from blink-182 to The Killers, SZA, Future & Metro Boomin, as well as Killer Mike, Victoria Monét, Tyla, Kesha and Skrillex bring out.

Some artists that have been brought out in the past as surprise guests have ranged from as big as Rihanna, Twista, Chance the Rapper, Tom Morello, Nelly Furtado, Jhené Aiko and R. Kelly. To not as big names such as Royce Da 5’9”, A$AP Mob, Vic Mensa, Ty Dolla $ign, YG, Omen and Jamie N Commons.

Three names that really come to mind and I wouldn’t be surprised to see making special guest appearances during one or two sets the weekend of Aug. 1st through 4th when Lolla hits Chicago’s Grant Park is Chance the Rapper, Gunna and Don Toliver. Chance having collaborated with headliners SZA, Future and Skrillex, as well as being from Chicago. So a strong possibility of him appearing during all or at least one of their three sets that Thursday, Friday and/or Saturday. But also makes you question with Chance being from Chicago why he isn’t even on the lineup this year, let alone a headliner like he would have been if he was on the lineup. Gunna is another name that makes sense too cause he has collaborated with both Future and Metro Boomin, so even though he didn’t appear on either of their collaboration album’s released earlier in the year. He could still make an appearance during their headlining set on the Bud Light stage on Saturday, Aug, 3rd. Having also collaborated with headliner Megan Thee Stallion and upcoming rising star, Tyla. There’s a possibility he could also make a guest appearance during one or both of their sets on the T-Mobile stage for Lollapalooza’s opening day of Thursday, Aug, 1st. Don Toliver having collaborated with headliners SZA and Future and Metro Boomin. Making it a good possibility he could appear for at least one or both headlining sets that Friday and Saturday. Future & Metro Boomin’s headlining set that Friday the more likely of a set that is most likely to have several guest appearances throughout the set. Lollapalooza founder Perry Farrell, almost assuredly making a surprise at someone’s set during the festival’s four days too. Another person that also could come as a surprise guest to play guitar for one or two sets from someone else is legendary rocker and original Chicago-area native, Tom Morello. Who’s set it would be though a good question.

Even though it is Lollapalooza’s 20th anniversary here in Chicago, aside from the artists I mentioned I still don’t see a whole lot of artists making guest appearances during sets throughout the festival. Unless it is of the variety of guests being brought out by other artists that are already performing that weekend. The biggest possibilities of cross-performances happening being Megan Thee Stallion bringing out Victoria Monét to perform their collaboration, Spin, from Megan’s most recent album, MEGAN, that she released in June. Which would likely be their first live performance of the track together too. Reneé Rapp also another good possibility for her to come out during Megan’s headlining set and/or during Reneé’s set she will be playing on the T-Mobile stage that Friday to perform their collaboration, Not My Fault, that was from the Mean Girls soundtrack released earlier this year.

Despite what big name guest surprises are brought out or not. It should be another really great and jam-packed Lollapalooza that I’m sure me and many others will be looking forward to a lot no matter what. With the gates for the festival opening almost exactly two week’s from today.