Tyler, The Creator Brings Out Igor During Lollapalooza Headlining Set: 5 Best Moments

Before Tyler, the Creator even took the stage for his headlining set on day two of Lollapalooza — the same day the city reinstated its indoor mask policy, which the festival is adhering to for its few covered spaces — it was clear he was going to put on a show from the props alone: some boulders, a boat, a locked chest and a signpost reading “call me if you get lost,” nodding to his latest studio album.

And when he walked on stage, they multiplied, as the artist — dressed as a bellhop — came out pushing a luggage cart stacked with suitcases plucked right out of his “Lumberjack” music video. His entrance set the tone for what would follow: part sketch show, part concert, as Tyler powered through his hits in an organized fashion (mostly performing tracks from his various albums in segments) in between interludes of lounge music during which he’d saunter back to the cart and tend to his luggage.

For a set so steeped in the concept of escapism, it oddly and unintentionally suited a moment in which 100,000 fans were seeking just that by attending the first major festival to return since the start of the pandemic — and as the COVID-19 Delta variant is on the rise. While Tyler never made any remarks on the return of live music as night one headliner Miley Cyrus did, to do so would have also pulled attendees out of the scene he aimed to set.

Here are the five best parts of Tyler, The Creator’s Lolla headlining gig.

The Theatrics

From the moment Tyler came on stage to the final second of his set, he acted as if every spare moment was part of a music video, moving intentionally with each step and smile. In fact, under his bellhop outfit was the very same look he wore in the “Lumberjack” visual — from the nail polish color to the leopard print shirt to the powder blue furry hat (under which he later revealed his slightly longer bleached blonde hair). Over an hour later, not much past his scheduled 10 p.m. end time, though he was no longer wearing his bellhop suit, the rapper snapped right back into character, loading up the luggage cart and slowly pushing it off stage… Only to then turn around as the camera zoomed in on his face, filled with a longing expression, before flashing a dazzling smile and exiting for good.

His Use of Props

Toward the beginning of his set, Tyler grabbed a Louis bag from the cart and brought it into the onstage boat with him for a quick ride. As the prop made jerky movements, as if floating over an uncertain sea, he performed the first five tracks off his latest Billboard 200 No. 1 album, Call Me If You Get Lost. And though Tyler ditched the bellhop costume quickly, he was soon replaced by the anonymous character of a fisherman in a bright yellow raincoat who was responsible for holding up a backdrop as Tyler set sail — and, of course, mock-mopping up the water on the dock once Tyler returned to land.

He didn’t stay on the ground for long, though. Moments later, Tyler was high in the clouds — he quite literally was lifted above the stage in a particularly fluffy-looking prop — to perform the swanky and affectionate “Sweet.” He mostly performed songs in segments, grouping tracks together by album starting with his latest, then into 2017’s Flower Boy, followed by his 2011 debut album, Goblin, then into a trio of tracks off 2013’s Wolf and finally, into Igor before delivering the latter half “Sweet,” “I Thought You Wanted To Dance,” to bring the show full-circle.

The Igor Cameo

Not only did Tyler perform the first few tracks off Igor, but he did so as Igor himself. Tyler momentarily disappeared as the stage lights dimmed, leaving the crowd to question where he might emerge from next — but no one thought to question who he would emerge as. Dressed in a lemon-lime green suit and donning Igor’s signature platinum blonde cut, Tyler managed to crank the energy up a notch — the festival grounds did in fact quake during “Earfquake” — as he went into rage mode for “New Magic Wand.”

His Self-Confidence

While Tyler didn’t directly mention the pandemic, he did recall the top of 2020 as a time when he felt “super proud of myself for where I’ve got in the past 10 years. It was interesting for me to see how I got there, so I wrote a song about it.” He then went into “Massa,” on which he sings about leaving L.A. for the first time, being a caterpillar emerging from a cocoon, and how even as his tastes started changing, “first impression is everything, ain’t wanna let me go.” But as Tyler proved throughout his set, he’s on his own journey whether you’re coming along or not.

His Commitment 

Tyler has so clearly proved his commitment to characters and entertainment over the years — evidenced during his headlining set by subtly returning to his role as bellhop for his grand exit, creating a narrative arch. But what he also proved was his commitment to himself. After swapping out his Igor apparel for a pair of shorts and plain tee, Tyler told the crowd “I’ve been doing this since 2011. N—-s told me for real, ‘You’re s—’s too weird, you’re gonna last six months.’ Now I’m headlining motherf—–g Lollapalooza.” “And I’m petty — that s— pushed me,” he continued as fireworks for Marshmello’s headlining set on the opposite end of the park lit up the sky. “It took 10 years, but if any of y’all got s— you’re working on, it might work in five days, 10 years, 20, but keep that s— running, please. I mean that.”