And we back, and we back, and we back…for yet another year of Lollapalooza. I haven’t missed a single day of the festival since it settled in Chicago back in 2005, so 2019 will mark my 15th year in a row of this madness in Grant Park. No, I’m not sure when I’ll finally decide to scale back and start skipping days or the festival entirely. Yes, I’ve slowly become older than most of the people who attend Lollapalooza these days. But the combination of age and experience leads to wisdom, which is something I’m happy to share with anyone planning to spend time at the festival this upcoming week/weekend.

The most basic advice I can give is to know your limits and practice rigorous self-care whether you’re in Grant Park for one day or all four. Drink lots of water (more than you want/need to), wear sunscreen and bug spray, and don’t be afraid to find a spot and sit down for a bit. The number of people I see collapse due to exhaustion, dehydration, or too much alcohol/drugs every year just makes me shake my head. Wear comfortable shoes (NOT flip flops). Avoid bringing a bag or purse if you can, because there are separate security lines at the entrance for bags vs. no bags and I’ll give you one guess as to which one moves at least 3x faster than the other. If you absolutely have to bring a bag, make sure you’re aware of the Allowed and Prohibited Items list before packing it. Also be very mindful of the bag’s size, shape, and number of pockets because there are restrictions on those things too. These might seem like a lot of things to remember, but the good news is that most of them are common sense anyway. Just be smart about it, and you should be fine.

But what about the music? Navigating sets from 180+ artists over four days isn’t easy by any stretch of the imagination, and the best advice I can give you for scheduling is to map out your day in advance and avoid going from one end of the park to the other too often. The walk end-to-end through Grant Park takes about 15 minutes wading through clusters of people, and you’ll exhaust yourself quickly by doing it more than 2-3 times per day. If you’re facing a difficult time slot conflict between two or more artists, you’d be best off just picking the one at the stage closest to where you are at that very moment. Simple enough! Not familiar with enough artists to fill your schedule for the day? Let me try to help with a list of five performances you shouldn’t miss on each day of the festival. Here we go:

Lennon Stella [2:45-3:30, Bud Light Stage]
Fans of the TV series Nashville already know who Lennon Stella is, but for those unfamiliar, the 19-year-old Canadian singer crafts smart and catchy pop songs that feel familiar but manage to distinguish themselves through strong and empowering lyrics. Yes, she’s toured with The Chainsmokers and 5SOS, but try not to hold that against her.

H.E.R. [4:45-5:45, T-Mobile Stage]
H.E.R. stands for “Having Everything Revealed,” and the incredibly honest and vulnerable R&B songs she composes certainly feel like they hold nothing back. Her self-titled debut earned massive critical acclaim and won the Grammy for Best R&B Album.

Saba [6:30-7:15, American Eagle Stage]
Chicago rapper Saba is coming off of a massive 2018 that included a world tour and the release of CARE FOR ME, an incredibly personal album about the murder of his cousin (and mentor) Walter Long Jr. Expect a deeply powerful performance focused on grief and loneliness, but with enough beauty and upbeat qualities to ensure it’s not a drag.

King Princess [7:45-8:45, Lake Shore Stage]
King Princess is a multi-hyphenate: singer, songwriter, multi-instrumentalist, and producer. She makes wildly fun yet intensely vulnerable pop music for the LGBTQ+ crowd, perhaps best evidenced by her hit single “Pussy Is God”.

The Strokes [8:45-10:00, T-Mobile Stage]
Sure, it seems like The Strokes only play occasional festival dates these days to make some nice cash before going back to their respective side projects, but their early records are modern classics and they still manage to put on a strong live show. Better catch them every chance you get, because who knows how much longer this will last?

The Nude Party [2:00-3:00, Lake Shore Stage]
Six-piece North Carolinian band The Nude Party very much fall into a category with The Black Lips (who produced their debut album) and Chicago’s own Twin Peaks, in that they’re a rock band with a penchant for strong guitar riffs, memorable hooks, and the desire to have a great time both on stage and off. They have the potential to put on one of the most interesting and exciting sets of the festival, so show up early to catch them!

IDLES [3:00-4:00, T-Mobile Stage]
Really though, if you want to elevate your blood pressure and maybe get aggressive in a mosh pit, no band is better equipped to satisfy your needs than Bristol punk band IDLES. Their second album Joy as an Act of Resistance was one of 2018’s best, a chronicle of sickness, loss, addiction, and recovery built on sloppy guitars and growled vocals.

Janelle Monae [6:45-7:45, T-Mobile Stage]
I’ve seen Janelle Monae perform a couple of times, and her show has been so special, memorable, and fun that I’d be an idiot not to recommend it. She’s got a lot of similarities to Prince, particularly in her sly way of blending funk, R&B, pop, and rock into something you can’t help but dance to.

Bishop Briggs [7:45-8:30, American Eagle Stage]
If you’ve heard Bishop Briggs sing, then you know her voice is extremely powerful and unparalleled. That she chooses to use it on such dark and intense yet soulful pop songs is a gift to the listener, and its turned her into something of an underground alternative star in a somewhat similar vein to Billie Eilish, Halsey, and Meg Myers.

Tame Impala [8:30-10:00, Bud Light Stage]
The Australian band that’s essentially just Kevin Parker and a bunch of hired hands have steadily built themselves into the dominant, more mainstream psychedelic bands of this particular era. Their live shows aren’t the most active or exciting things to watch, but they do sound great and use visuals that will certainly enhance the songs if you’re not completely sober.

Men I Trust [1:45-2:45, Lake Shore Stage]
If you’re looking for a very chill way to start your Saturday, Montreal band Men I Trust will satisfy nicely. Their specialty is blissed out dream pop that will get your head bobbing and toes tapping while you slowly come to realize that the lyrics are far darker and more disturbing than the melodies might otherwise imply.

Jade Bird [2:50-3:30, American Eagle Stage]
British singer-songwriter Jade Bird released her self-titled debut album earlier this year, and it’s packed with fantastic songs that blur the lines between country, folk, rock, and blues. Her voice has a slight twang to it that’s reminiscent of Dolly Parton or Shania Twain, but it’s clear Bird is intent on carving her own path and has already found a strong and adoring fan base.

Gary Clark Jr. [4:45-5:45, T-Mobile Stage]
All due respect to Slash, but Gary Clark Jr. is probably the most talented guitar player at Lollapalooza this year. His version of modern blues pulls from the greats like Stevie Ray Vaughan and Jimi Hendrix, then adds in a fair amount of experimentation and biting social commentary to send both a powerful and immensely compelling message.

Yaeji [6:30-7:15, American Eagle Stage]
New York-based producer Yaeji loves to play around with style and form in her music, developing melodies and rhythms common in house, downtempo, and electro while singing or rapping in both English and Korean. Her live show is basically just one huge and wildly fun dance party, though thankfully it’s a bit of a different vibe compared to what’s going on at the Perry’s stage.

Tenacious D [7:00-8:00, Bud Light Stage]
The comedic rock stylings of Jack Black and Kyle Gass (aka Tenacious D or The D if you’re in the know) manages to entertain on multiple levels. Whether they’re facing off in a guitar battle against Satan or simply going through some “difficult personal shit” with one another, you’ll both laugh and have your face melted off.

G Flip [2:50-3:30, American Eagle Stage]
Australian singer-songwriter, producer, and multi-instrumentalist G Flip bears a lot of resemblance on paper to someone like Tash Sultana, who has a very similar skill set and approach to music. But G Flip stands on her own, crafting addictive synth-pop tracks in her bedroom, many of which have been collected for her forthcoming debut album due out at the end of August. Don’t be surprised if she breaks out in a big way before the end of 2019.

The Revivalists [4:30-5:30, T-Mobile Stage]
Eight-piece New Orleans band The Revivalists chose the right name, because almost all of their music sounds like it was pulled from classic blues, funk, and soul recordings. You’ve probably heard some of their songs on the radio, but on stage they’re even more of a behemoth, showcasing dynamite guitar solos and a vibrant horn section.

ROSALIA [6:00-7:00, Tito’s Handmade Vodka Stage]
Rosalia’s global success is a testament to the boundless power of pop music. Her second album, 2018’s El Mal Querer, managed to earn all kinds of attention and critical acclaim thanks to its ability to blend postmodern flamenco sounds with today’s R&B flash. The mixture is so intoxicating, superstar musicians are lining up to work with her.

Mitski [7:45-8:30, American Eagle Stage]
Lollapalooza appears likely to be Mitski’s last Chicago date for the foreseeable future, as she’s planning to take an indefinite amount of time away from music so she can focus on life and being a person in the world. Similar ideas and themes can be found all over her records, including last year’s highly acclaimed Be the Cowboy, digging deep into anxiety and vulnerability while retaining a strong sense of self in both the abrasively loud guitar moments and the beautifully soft ones.

Ariana Grande [8:30-10:00, T-Mobile Stage]
It’s pretty safe to argue that Ariana Grande is the biggest pop star in the world today. The fact that she’s headlining a festival like Lollapalooza is a real treat, even though she just played two arena dates in Chicago back in June. Grande gave us two fantastic records over a six month period from 2018-19, both of which are packed with addictive and memorable singles. If the songs themselves don’t draw you in, hopefully her four octave vocal range will.