BY TER STAFF

In 2014 our Editor-in-Chief and lead photographer Dan Garcia teamed up with Pigeons & Planes to cover Lollapalooza, live at Chicago’s Grant Park. Returning to the festival the next year, Garcia got to witness some of the best moments from the premiere festival in the past couple years. Returning to Grant Park this year, Lollapalooza is expanding the festival to include a fourth date for its 25th Anniversary, and many expect festival organizers to release its best lineup yet by the end of the month. So to celebrate Lolla’s 25th Anniversary and built up anticipation until it’s forthcoming lineup is announced, we are sharing some of our favorite moments and photos from Lollapalooza since our publication’s inception.

Childish Gambino Performs In The Pit During the Pouring Rain (2014)

In 2014, Childish Gambino was performing a ton of tour dates and festival gigs in support of his newest LP, Because The Internet. However it is hard to imagine that any of those performances stood out more than his memorable performance at Lollapalooza in 2014. Performing in the middle of a huge storm, just a few hundred feet west of Lake Michigan, Childish Gambino decided to enjoy the weather with his fans, less than a song into his setlist. Almost two years removed from the performance, we can still remember this performance like it was yesterday.

Raury Travels to Chicago for His First Time Ever (2015)

Last year, emerging singer/rapper Raury traveled from his home in Atlanta to the Windy City, for his first time ever. Never having traveled to Chicago for anything, none-the-less a huge performance at Lollapalooza, it was certainly a big day for the ‘God’s Whisper’ singer. He must have had a good time too, as Raury returned to Chicago less than a month later for the filming of his music video ‘Friends’.

Eminem Recruits Rihanna and Returns to Lollapalooza After a Memorable 2011 Performance (2014)

Ask fans who were lucky enough to go to Lollapalooza in 2011 and they will tell you that Slim Shady stole the show. So when fans had another chance to catch Eminem on the Lollapalooza stage, they quickly jumped on it. Fans lined up outside before the festival gates opened and rushed to the Samsung Galaxy Stage to get a good spot for Eminem’s headlining set. And like 2011, Eminem again delivered in 2014 and this time with some help from Rihanna!

Vic Mensa Nearly Dies Sneaking Into Lollapalooza, 4 Years Later He Performs There (2014)

A spot on Lollapalooza’s lineup couldn’t have meant more to anyone than it did to Vic Mensa in 2014. Just four years earlier, Vic Mensa nearly died after he fell off a bridge and was electrocuted while attempting to sneak into the Chicago festival. Who would have guessed that years later he would get the call from festival organizers, asking if the Chicago rapper would like to perform? Vic gave an energetic performance for his hometown crowd and even brought out his longtime friend and fellow Chicago native, Chance The Rapper, to perform a couple of their collaborations.

The Weeknd Brings The Madness to Lolla (2015)

The Weeknd landed a few headlining festival sets last year, including a couple especially big ones with Coachella and Lollapalooza. And while each of these performances were equally great, a lot changed for the Beauty Behind The Madness singer in the few months separating the festivals. In that short time, Abel catapulted to being one of the biggest names in music, in large part thanks to his mega single, ‘Can’t Feel My Face’. While both the California and Chicago crowds got to see a great set from The Weeknd, Chicago got to see a newly crowd R&B superstar.

Andre 3000 Unveils a Classic Lolla-Look During Outkast’s Reunion Tour (2014)

As anyone who loves music will remember, Outkast went on a huge festival reunion tour in 2014. Kicking off their festival tour at Coachella, Outkast eventually made their way to Chicago for a headlining set at Lollapalooza. And while his all black jumpsuits were consistent throughout his appearances (only changing the text of each suit), Andre 3000 brought these talked about jumpsuits to Chicago, and doing so he instantly had a classic Lolla-look. That night’s performance, the jumpsuit asked fans “across cultures darker people suffer most. why?”, of course that question was not answered, but Outkast put on a great show and everyone in Chicago got their fix of nostalgia.

Lorde Delivers for Her First Ever Lollapalooza Performance (2014)

After coming to Chicago on her headlining tour with ‘Riptide’ singer Vance Joy, Lorde hinted to fans that she would be coming back to the Second City real soon. And she kept her promise as Lorde returned to Chicago in 2014 for a memorable Lollapalooza appearance. In an iconic pair of black overalls (iconic to those who were there at least), Lorde performed the majority of tracks from her debut album Pure Heroin, as well as an awesome cover of Son Lux’s track ‘Easy’.

Paul McCartney Performs a Massive 31 Song Setlist (2015)

You pretty much have to be a Beatle to get the approval from festival organizers to have a 2 hour and 15 minute set, and given all the talent at Lollapalooza, it makes sense. But this rule held true as Paul McCartney had the green light to deliver one of his awesome lengthy (and rightfully so) performances. In total, Sir Paul performed a massive 31 song setlist, with a 7-track encore that ended the night with a performance of the classic Beatles’ record, ‘The End’.

Jhene Aiko Makes Us Fall In Love (2014)

Jhene Aiko’s infectious smile alone will make you a fan, and it’s just a bonus that her music is as good as her 2014 Lolla-look was cute. Performing on Sunday morning of Lolla in 2014, hours before her friend and collaborator Donald Glover gave his memorable performance in the pouring rain, the sun was still shining for Aiko. Her Chicago fans were in attendance, and she surely picked up some new ones as well. Let’s just hope that Aiko soon returns to the premiere Chicago festival.

Chance The Rapper Headlines for His City (2014)

2014 was not the first time Chicago’s Chance The Rapper hit the stage at Lollapalooza, but it was definitely his most memorable Lollapalooza performance, and perhaps his biggest show to date. Chance had a huge year in 2014, after some huge co-signs and the growing success of his Acid Rap project, Lollapalooza capped it all of. “Lil Chano from 79th” returned the favor and brought out Vic Mensa for an awesome performance of ‘Cocoa Butter Kisses’ and he even brought out R. Kelly for ‘Ignition’! With The Social Experiment to back him up, and beautiful view of his hometown fans and Chicago’s skyline in front of him, Chance put on one for the ages.