Janelle Monae, Twenty One Pilots, Childish Gambino lead top 10 Lollapalooza sets to catch  

Lollapalooza 2019 Janelle Monae photo by Daniel DeSlover

Tons have tried to imitate but not a single one has ever been able to duplicate Lollapalooza, the former traveling festival that’s since set up shop in Chicago for what feels like forever. The 2019 installment (coming to Grant Park August 1-4) actually marks the mega festival’s 14th year here, and like the extensive lineage that came before, this one definitely has its fair share of must-see sets. So whether it’s rock, hip-hop, pop, country, EDM or a mash-up of pretty much anything, there’s surely something for everyone, though just in case anyone’s having trouble making choices, here are ten essentials spread across several stages and all four dates.

1. Janelle Monae (August 2 at T-Mobile)
Landing somewhere between a present tense version of Prince and Janet Jackson with her own twist on pop, rock and soul, Janelle Monae is well on her way to headliner status. The insatiable grooves and topical songwriting from her latest long player, “Dirty Computer,” are worth the price of admission alone, while her enthralling chorography and visuals add extra sizzle to a lengthy list of artistic assets.

Lollapalooza 2019

Kacey Musgraves photo by Andy Argyrakis

2. Twenty One Pilots (August 3 at T-Mobile)
Rarely has the alternative scene spawned such an attention-commanding band as Twenty One Pilots, who’s wall of sound is much mightier than one would normally expect from a mere duo. Besides dripping with just as much charisma as sweat when they toss on their ski masks in the heart of summer, Tyler Joseph and Josh Dun’s incorporation of indie rock, hip-hop and electronics over instantly relatable themes makes for one of the weekend’s most exciting hybrids.

3. Childish Gambino (August 2 at T-Mobile)
The man born Donald Glover, who also happens to be an enormous actor under that very name, hinted his hip-hop days as Childish Gambino may be coming to an end (at least as far as concerts are concerned). In other words, don’t miss a millisecond of this dynamic entertainer and social justice advocate behind the global game-changer “This Is America” in what’s bound to be a landmark Lollapalooza moment.

4. Kacey Musgraves (August 4 at T-Mobile)
She technically started as a country-minded singer/songwriter, but Kacey Musgraves is a full-fledged crossover queen after stunning with her “Album Of The Year” Grammy Award for “Golden Hour.” It turns out the attention is more than justified given her super sweet voice and clever, frequently tongue-in-cheek storytelling, all of which has contributed to a massive fan base spanning many walks of life.

5. The Strokes (August 1 at T-Mobile)
Calling The Strokes’ bill-topping kick-off a reunion wouldn’t entirely be true since the garage rock revivalists never really went away. But having all the guys back together following solo projects and no other area tour date makes this Lollapalooza stop a significant undertaking that’s likely to take a cue from its perfectly titled prior EP, “Future Present Past.”

Lollapalooza 2019

The Strokes’ Albert Hammond Jr. photo by Andy Argyrakis

6. Slash (August 4 at Lake Shore)
Being a co-founding member of the classic Guns N’ Roses line-up is enough of a reason to make guitar god Slash a priority. The fact that he’s joined by Myles Kennedy & The Conspirators makes for a mighty bonus, who are bound to perform plenty from their collaborative album, “Living The Dream,” plus the possibility for past GNR and Alter Bridge essentials.

7. NF (August 2 at Lake Shore)
Often cited as the second coming of Eminem, rapper Nathan John Feuerstein is bringing a series of thought-provoking rhymes and razor-sharp hooks smack dab between the immensely anticipated slots of Janelle Monae and Childish Gambino. In other words, NF will automatically attract a massive amount of eyeballs anyway, but is still destined to deliver thanks to smash singles such as “Let You Down” up through the super fresh sounds and lyrical substance of “The Search.”

8. Gary Clark Jr. (August 3 at T-Mobile)
With blues as his foundation on top of several rock, hip-hop and electronic shades, Gary Clark Jr. is bridging genres and generations. His latest undertaking, “This Land,” tackles racism and other urgent issues head-on, but ultimately evokes a communal spirit as he prodigiously wails on the six-string.

Lollapalooza 2019

Loud Luxury photo by Andy Argyrakis

9. Lauren Daigle (August 1 at Tito’s Handmade Vodka)
She’s drawn frequent comparisons to Adele and could legitimately give her some serious vocal competition, but Lauren Daigle simultaneously pulls from her own source of soulful pop and spiritual inspiration. The troubadour isn’t shy about expressing her Christian faith, but it never comes across as preachy, ensuring an inclusive environment for anyone seeking out someone who’s quite possibly Lollapalooza’s largest voice.

10. Loud Luxury (August 3 at Perry’s)
Modern house music is in extremely capable hands courtesy of Loud Luxury, the Canadian DJ duo that’s been racking up the streams and tag teaming with Bryce Vine, Brando and Anders. Whether spinning other people’s tracks or originals, plan for a non-stop party of explosiveness that can make even a field filled with the sunniest sky feel like a packed club at the stroke of midnight.


Lollapalooza comes to Grant Park Aug. 1 through Aug. 4. For additional details, visit Lollapalooza.com.