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20 Acts To See at Lollapalooza 2019

Another Lollapalooza is (almost) here and I can’t believe I’m saying that I’m attending all four days AGAIN! I definitely thought it would be the end of going all weekend last year but I mean it this time when I say it’s probably the last of the four days for me. Although Lolla and music festivals in general are definitely a splurge, I can rationalize spending $395 on four days of music over $160 on one day. It’s so wild to me that going for two days (purchasing two one day passes) costs $320 and paying $75 more gets you in for TWO MORE DAYS! So I will either continue to go for four or only go to one…maybe I can convince Lollapalooza to start selling 2-day passes?

I’m excited to share this post for the fourth year in a row! Fun fact, the first post I ever created for this blog was for Lollapalooza 2015. Time goes by so fast and it’s truly terrifying.

The day-by-day lineup took FOREVER to come out this year, assuming because Lolla was trying their very hardest to get the 4-day passes to sell out – as I type this, they are still on sale. As long as the fest sells out completely I’m sure they will continue to make it four days…but I wouldn’t be mad if they switched it back to three. I can find plenty of music I like each day, but it just gets exhausting the older you get.

This year’s lineup was split up pretty weirdly for me, as Friday & Sunday are days I’m far more excited for whereas Thursday and Saturday are a bit slower for me but for different reasons. Saturday’s headliners are just not for me and it’s a little annoying that the two headliners I’m least interested in seeing this year happened to get the same evening to perform – but that’s life. It’s going to be really shitty to pick Childish Gambino over Tame Impala – I’m not a die-hard Tame fan but their music has been growing on me a lot and I’ve loved the singles they have released this year. I know lots of other people feel the same way about the conflict. In an ideal world, I would be seeing Childish, Tame and Ariana Grande, but I don’t go to Lollapalooza for the headliners so it is what it is!

Per usual, I’ve compiled a list of twenty undercard acts (five per day) that I think are worth checking out. There are definitely people I left out on my list, and I purposely don’t highlight headliners or sub headliners since I assume that enough people already know about them / like them, and most of the Lolla fun is being able to discover new artists that you will be able to see perform. Each day features acts in alphabetical order and I will be sure to add their set times when those are released. Don’t forget to follow my Lolla 2019 playlist here. Enjoy!

10 Acts to See at Lollapalooza 2015
20 Acts to See at Lollapalooza 2016
20 Acts to See at Lollapalooza 2017
20 Acts to See at Lollapalooza 2018


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Alexander 23

Genre: Indie Pop
For Fans Of: Lany, Lauv

For someone who only has ONE song released on Soundcloud and Spotify, Alexander Glantz is doing incredibly well for himself. Signed to Interscope Records in 2018, Alexander’s debut single “Dirty AF1s” was released on March 14 of this year. The song, which appeared on Spotify’s “New Music Friday” playlist, is already approaching 800,000 streams and will probably reach it once this article is published. The song instantly caught my attention and ended up being one of my favorite songs released during the month of March. I had shared the song on my Twitter feed after I heard it and someone out of the blue had replied to me that he’s ironically from the Chicago suburbs (as am I) and it turns out that we grew up in neighboring towns. That stranger on Twitter looks to be a family member of Alexander’s, so that’s sweet.

Alexander 23 is currently touring with Alec Benjamin, another artist I have written about and is also playing at Lollapalooza this year. I will be curious to see if he has any more music released before August – assuming that he will since it’s hard to fill a set with just one song. If I’m able to hit the fest early enough on the first day I will definitely be checking out his set and look forward to see what’s coming next for him.

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Cautious Clay

Genre: Indie Pop/R&B
For Fans Of: Gallant, Khalid

If you’ve read my blog for a decent amount of time,  you know that I’ve been covering Cautious Clay for awhile at this point and that I was able to over his first ever show in Chicago last fall. While I thought he was very talented and enjoyed his performance that featured a handful of different instruments (guitar, flute and saxophone), I thought he needed more time to work on stage presence and overall confidence as a performer – which is something that obviously comes with time and more experience. I think that by the time Lollapalooza rolls around, Clay (real name Joshua Karpeh) is going to come full circle with a great show returning to Chicago after almost a year of more growth and more music released.

Cautious Clay was initially a music producer and found success in that realm before he was inspired to start creating and releasing his own music. He found major success with his song “Cold War” – a song about the frustrations of dating in this day and age and how he wishes we could just all be a little more honest with each other. I can’t say I disagree in the slightest!

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Harry Hudson

Genre: Folk Rock
For Fans Of: Hozier, Jon Bellion

Harry Hudson is someone I have been meaning to listen to fully for literally almost a year –  but you know how that goes. After recognizing his name on this year’s Lineup, it was the final reminder I needed that I really needed to check out his music in-depth.

Google tells me that Hudson, now 23, was diagnosed with Stage 3 Hodgkin’s lymphoma at age 20, and was the subject matter for a lot of his earlier music. His debut album was released in March of 2018 under Roc Nation and he has toured with Kygo.

Hudson actually played a set at Lollapalooza’s Bud Light Dive Bar sessions last year and I saw about 10 minutes of it not knowing who he was. It’s interesting because he wasn’t actually on the lineup but got to perform a mini set and was the opening act for Lany’s after show during last year’s Lolla. Hudson is a good friend of both Jaden and Willow Smith and has collaborated with Jaden in the past on the song “Just Slide.” Together, Hudson and Jaden have launched a “art collective and lifestyle” brand together called MSFTS.

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Genre: Indie Pop
For Fans Of: Lany meets Twenty One Pilots

I only recently stumbled upon half alive and of course it was just a couple weeks before they were performing a headlining show in Chicago with Joan, another similar sounding band who I’m surprised is not on the Lollapalooza lineup this year.

half alive is a band based out of Long Beach, California. Lead singer Josh Taylor had decided to start a new project after performing in a band called The Moderates and with help of new bandmates Brett Kramer and J Tyler Johnson, the band released their first single titled “Still Feel.” in 2018.  The song and its accompanying music video garnered widespread praise and eventually led the group to sign with RCA later that year (who (Bleachers, Cage The Elephant, MUNA). Their quick success lead to a sold out North American tour and performances at this year’s Firefly, Outsidelands and Lollapalooza festivals, as well as another tour this fall in North America and Europe.

The band has interesting themes throughout their music surrounding religion and anxiety. I look forward to hopefully checking out their set this year and can’t imagine it’ll be much longer until they’re larger than life.

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Lennon Stella

Genre: Pop
For Fans Of: Taylor Swift, Léon

Another person I’ve recently been LOVING! Lennon Stella first made her mark on the music scene uploading adorable videos singing with her younger sister onto YouTube when they were both very young (she’s only 19 still) and then later receiving roles on the tv show “Nashville” alongside Connie Britton and Hayden Panettiere.

Lennon signed with Columbia Records in January of 2018 and was later featured on a track with Jonas Blue and Liam Payne, formerly of One Direction during the same year. Her debut EP, Love, me was released in November 2018 and features songs like “Bad,” “Breakaway” and “La Di Da,” three songs that nearly combine to 60 million streams on Spotify.

Though Stella’s songs are inherently catchy pop songs to begin with, they are made even more consumable due to her truly lovely vocal abilities. Stella has a very raspy, full unique voice that brings life to songs that otherwise may seem average for a pop star who doesn’t have such strong vocal capabilities. This is probably due to being born to musicians and being exposed to music and singing at such a young age. One of the artists I’m most interested in seeing this year.

Headliners I plan to see on Thursday: Honestly, probably planning to check out a bit of all three. It’ll definitely be The Chainsmokers (slight cringe) against The Strokes against one smaller act on The Pepsi stage. Bouncing around between headliner sets sounds like the best way for me to end Thursday evening.

Subs I plan to see: If you don’t already know, the sub is the artist who plays on the main stages before the headliner. They tend to perform anytime between 6-7:45pm. My guess is this slot will be taken by Hozier, so that’s who I will FINALLY be seeing!


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Genre: Indie Rock
For Fans Of: Foreign Air, Walk The Moon

Dreamers is a band that I’ve been a fan of for a couple years now and I seem to miss every chance I have to see their show when they hit Chicago – so hopefully I don’t miss them this time around! Dreamers launched in 2014 and were signed to Fairfax Recordings in 2015 for their debut EP, released later that same year.

The band has released a handful of EPs and albums since and have had success touring with artists like Atlas Genius, Catfish and The Bottlemen and All Time Low. Just a year or so after their official launch in 2014, Dreamers won a spot opening a handful of shows with Stone Temple Pilots – beating 500 other bands who submitted to open. Not too bad!

Dreamers made their debut at Lollapalooza in 2016 and I’m sad to say I wasn’t familiar with their music back then. Since I’ve become a fan of their sound, especially their 2019 singles – “Die Happy” and “Insomniac.” The singles are promoting their next album which drops TOMORROW – April 26! Perfect timing on my end, if I say so myself.

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Conan Gray

Genre: Pop
For Fans Of: Troye Sivan, Lorde

The second I heard Conan Gray’s music for the first time, I was HOOKED. Not only is he another young talent to watch, but he has a genuinely interesting voice and clever lyrics about what it’s like to be a teenager living in 2019 and has a point of view similar to one of his idols’, Lorde, – & just as captivating.

A self-identified “professional over-thinker,” Gray started writing songs as a 12-year-old growing up in the small town of Georgetown, Texas and was influenced by artists like The Dixie Chicks, Adele and Lorde.

“Hearing the Lorde album was a cataclysmic experience for me,” says Conan. “It was the first time I’d heard pop music that was about normal suburban life.” 

During Gray’s senior year of high school, he was kicked out of his parents’ house. Luckily this was around the same time Gray captivated the attention of managers Colette Patnaude and Eddie Wintle after finding Gray’s YouTube channel. Gray ended up enrolling in UCLA and moving to Los Angeles – which led to him signing a deal with Republic Records and working with Dan Nigro (Carly Rae Jepsen, Sky Ferreira, Kylie Minogue) on his self-written debut EP, released last year.

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Omar Apollo

Genre: Indie Pop/R&B
For Fans Of: Cuco, Rex Orange County

Another gem I recently discovered! Omar Apollo grew up in Indiana just about an hour outside of Chicago after his parents moved his family to America from to Mexico and opened up their own taco restaurant. His story is so cool now that he’s able to support his family with his music.

Apollo cites his parents as his main motivation for learning how to play guitar, sing and produce music. His debut EP dropped in 2018 and he gained a heavy stream of fans due to his bilingual song titles and funky bass lines. I like Apollo particularly because I think he and his family represents the idea of what it means to come to America to pursue a better life and how to find success, which is a narrative that basically half of our country is against right now. But despite the odds and the negativity, he’s out here doing amazing for himself.

His latest EP dropped on April 10 and he’s currently on tour with artists like Dreamer Boy and Role Model.

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Genre: Pop
For Fans Of: Taylor Swift, The Aces

Another artist I’ve been following for awhile who is finally making her debut at Lollapalooza! I was shocked to see that she wasn’t on the lineup last year, so this is definitely a long time coming. Sigrid Solbakk Raabe is a 22-year-old Norwegian pop singer who’s been making waves over the last two years or so for her electric bubble gum pop. Sigrid has been finding success across the pond after winning the BBC Music Sound of 2018 award, which is voted by music critics and industry figures in the UK to find the most promising new music talent. Artists who have won this award in the past include Adele, HAIM and Sam Smith.

Sigrid’s debut album Sucker Punch was released in March of 2019 and although I prefer a lot of her singles and songs on previously released EPs, I am certain that she’s going to put on a great performance based on the amount of international buzz she’s been receiving for the past 20 months or so.  She just wrapped up a tour supporting George Ezra in Europe and will be touring with Maroon 5 this June.

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Tierra Whack

Genre: Hip Hop
For Fans Of: Noname, Rico Nasty

If I am voluntarily writing about hip hop music YOU KNOW IT IS GOOD. I knew who Tierra Whack was over the past year or so but didn’t really get into her music until her song “Only Child” was released earlier this year – I may have listened to it a bit TOO m much based on how much I love it but I think  that’s a good sign.

Tierra Whack (yes, her real name) is another young artist to watch at just 23-years-old. Whack’s debut album, Whack World, came out in 2018 and received critical acclaim, despite it only being a total of 15 minutes long: each song was just 1 minute long. What’s really cool about Whack is she grew up writing poetry and is even an accomplished spoken word performer, two aspects about her talent that really do make sense as to who she is as an artist.

Whack performed at this year’s Coachella (video here) and toured with 6LACK – another artist on this year’s Lolla lineup – last year. Curious to see where her next album (unannounced) takes her.

Headliners I plan to see on Friday: Again, really sad I have to choose Gambino over Tame, but it’s an easy decision for me. I’ve seen Childish Gambino three times and will be very excited to see his R&B stuff live in addition to whatever rap he decides to play. Either way I’m here for it.

Subs: Janelle Monaé! Maggie Rogers! Sad I will LIKELY be missing Death Cab For Cutie AGAIN for Monaé- a band I’ve been dying to see since I was 14 – but it’s no competition.


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Bad Suns

Genre: Indie Pop/Rock
For Fans Of: Coin, Bleachers

Are you sick of me talking about Bad Suns yet? You shouldn’t be, considering how long of a gap existed between Bad Suns’ second and third albums. The band’s first two albums were released under Vagrant Records in 2014 and 2016, respectively, but Mystic Truth wasn’t released until earlier this year – due to the fact that Bad Suns was home to a new record label at Epitaph.

Bad Suns has had extensive touring experience through their own headlining tours and supporting artists like The 1975 – I saw the two perform way back in 2014 (wow) in Madison, Wisconsin when I was a freshman in college. Although I prefer Bad Suns’ first two albums over their newest release, they are solid performers and their debut at Lollapalooza has been LONG TIME COMING. I seriously can’t believe it’s taken them this long to get a slot, considering that they played at Coachella way back in 2015 and have had NUMEROUS shows in Chicago – even one this weekend at the House of Blues (which is sold out). I’m expecting this show to be a homecoming as sorts for the group, since I know they have a solid fanbase who have been waiting for them to hit this festival specifically.

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Bea Miller

Genre: Pop
For Fans Of: Ariana Grande, Julia Michaels

If you are a fan of talent shows like American Idol and The Voice like me, you’re probably just as satisfied when you see past contestants find success after and without the help of the show. That’s how I feel about Bea Miller, a 20-year-old pop musician signed to Hollywood Records (Demi Lovato, Sabrina Carpenter) who came in 9th place on the second season of “The X Factor US” in 2012 (as I looked up this information, I really spiraled down a rabbit hole). She was only 13!

Miller’s debut EP was released in 2014 and she toured with Demi Lovato the same year. Her debut album Not An Apology was released in 2015 and it peaked at #7 on the Billboard 200 Charts. She later toured with Fifth Harmony and Selena Gomez, releasing her second album in February 2018, called Aurora. The album covers issues ranging from “existential boredom,” slut shaming and gun control. Pretty heavy topics from a 19-year-old!

Miller’s latest track with fellow Lolla performer 6LACK “It’s Not U It’s Me” has been on REPEAT for me over the past month. Hopefully I get to hear it live this summer!

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Jade Bird

Genre: Folk/Pop
For Fans Of: First Aid Kit, Joseph

I know I’m a broken record saying this, but this is another artist that I’ve been following for awhile now! I first heard Jade Bird’s single “Lottery” towards the end of 2017 and truly became obsessed with it – so much so that it ended up being my third most played song of 2018 (s/o to Spotify for that data).

I had a gut feeling that she’d be playing Lolla this year after announcing that she would be supporting Hozier on tour this spring – who I also assumed would be on the lineup. While I don’t tend to enjoy lots of country folk music, I do have some artists that end up being the exception – and Jade is one of them. Her lyrics are ferocious and fun, her voice is phenomenal, and overall just exudes a great vibe that is confident but not over the top.  I JUST realized as I write this that she’s another one of the artists on the lineup who is extremely young – she’s only 21. Does that make anyone else feel worthless?

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Men I Trust

Genre: Indie Rock
For Fans Of: Snail Mail, Phoebe Bridgers

I first discovered Men I Trust after learning that they would be the opening act for Wild Nothing, a band that I was thinking about going to see at Thalia Hall last fall in Chicago. Although I ended up not going, I learned about another band that I ended up loving which is always fun. Men I Trust is a band based out of Montreal founded in 2014 by two high school friends, Jessy Caron and Dragos Chiriac. The two were reunited at Université Laval, a research college in Quebec. With the help of fellow classmate Emma Proulx, they self-released an EP in 2014 and performed at a handful of festivals in Montreal.

Men I Trust’s first album was released in 2015. Their sound has been described as “foot-tappy rhythms with calm melodies and chilled-out vocals reminiscent of Sia’s in the early aughts” and “bouncy, easygoing, stress-free appeal” by NPR music in a highlight piece about artists to watch at SXSW 2018.

Men I Trust just debuted at Coachella, is about to tour in Europe and will be playing Summerfest later this year before they hit the stage in Grant Park.

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Sam Fender

Genre: Indie Rock
For Fans Of: Nothing But Thieves, Hozier, Catfish & The Bottlemen

You know when you hear someone’s music for the first time and you are just instantly captivated in everything they are doing? That’s how I feel about Sam Fender, a 24-year-old musician from England who was named one of BBC’s Sound of 2018 artists alongside fellow Lolla performers like Sigrid, Lewis Capaldi and Khalid.

Although he doesn’t have much experience as a musician so far, Sam Fender’s clear point-of-view as a musician with politically captivating lyrics and gritty vocal abilities got him to the top of the Spotify viral charts for two weeks in 2017 (#2 spot) for his track “Play God,” a song that is very clearly about our current president. He even has a song with “Kardashians” in the title. Can you guess the subject matter?

We idolize idiots /  Masturbate to their sex tapes / We love them we hate them / We wan to see them fall from grace / We laugh at them disheveled  On the front page of The Mail
Then grab ourselves a pitchfork / and go in for the kill / Together light vigils
Eulogize them on the Internet /  when they top themselves

Fender’s debut album is out just a few days after his performance at Lollapalooza – August 9. A shame we won’t get it in time, for Fender is another artist I am most looking forward to seeing this year at Lollapalooza and one I GUARANTEE will be huge in 2020. You can QUOTE ME.

Headliners I plan to see on Saturday: None of them. I’ll be heading home by 8pm. I’m really hoping Mitski gives us an after show and if it’s on Saturday, it’s even better.

Subs: Depending on how the day is going I will check out Gary Clark Jr. for a bit.


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Genre: Indie/Dream Pop
For Fans Of: Ten Fé, Bombay Bicycle Club

In a world of overproduced songs (a quality that tends to really irritate me), Bayonne is a self-proclaimed “minimalist composer.” Based out of Austin, Texas, Bayonne was originally releasing solo music under his name Roger Sellers, and decided to change his moniker to Bayonne in 2016. He re-released an album from 2014 under his new stage name and another earlier this year titled Drastic Measures. This is the album that caught my attention.

Sellers became a major fan of Phil Collins when he was just six-years-old – his parents got him his first drum set at that age, which led to him learning to play classical piano and even studying music theory in college.

I think it is really difficult to create indie or dream pop music that 1) isn’t gimmicky and 2) doesn’t sound like everything else. Bayonne is able to avoid both. He is also a master of  looping his music live – which confuses people when he tells them he is NOT a DJ.

“I want the music to carry people in some way, and I want them to feel what I’m feeling. I want my music to be an emotive expression.” 

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Genre: Indie Pop
For Fans Of: Billie Eilish, Lorde

Another name that those of you who have followed my writing for awhile should recognize! My relationship with Bülow dates way back to December 2017 when she personally reached out to me as an artist on the rise hoping to get her music featured on Ones To Watch. It eventually led to a question and answer article (here) and her career has SKYROCKETED since we ever first exchanged emails.

(Megan) Bülow was discovered in the summer of 2016 at a music camp and immediately began working with Canadian writers and producers. Her debut EP was released in November 2017 on Wax Records – a label under Republic Records – a label home to superstars like Ariana Grande and most recently, Taylor Swift.

Bülow has been compared to the likes of Billie Eilish and Lorde for her unique sound and take on pop music with darker themes of drugs, partying and falling in and out of love. There are so many young female artists taking the stage at Lollapalooza this year and I am AMPED!

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G Flip

Genre: Indie Pop
For Fans Of: Maggie Rogers, Mallrat

How cool is the name Georgia Flipo? That’s G Flip’s real name – a multi-talented musician from Melbourne, Australia. Once a drummer & backup singer for the Melbourne based band Empra, G Flip released her first solo music in 2018 – moving so fast to even perform her first solo set at South By Southwest in the same year. Her first single, “About You,” landed on YouTube’s New Music playlist immediately after release and was named “Best New Track” by Pitchfork – which is no easy feat. They also said she sounded like “all three HAIM singers singing at the same time.” Not bad.

I basically owe Spotify my life because of how much new music I find due to their playlists, and G Flip is no exception. I was obsessed with her song “Killing My Time” last year and it ironically popped up in my library again just a couple weeks before I saw she would be performing at Lollapalooza this year. G Flip has released a couple more new songs in 2019 and just recently, a track called “I Am Not Afraid.” No word on an extended release yet, but I wouldn’t be surprised if it comes out this year!

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Genre: Indie Rock
For Fans Of: Florence & The Machine

For someone who was given the title for Album Of The Year In 2018 from a number of respectable music outlets (including my own, HA), you’d think that Mitski would be ranked higher on this year’s Lollapalooza lineup…but I digress. Mitski is booked 12th out of 42 artists on Sunday and 44th on the lineup overall – I will be super curious to see how long her set time is going to be. After an amazing year for Mitski including a TON of touring nationally and internationally, she has a handful of festival performances this summer including stops at Boston Calling, Governor’s Ball, Fuji Rock Festival and more. I was expecting her to be a shoe-in at this year’s Pitchfork Festival, so it’s going to be interesting to see the type of demographic she pulls at Lollapalooza and I hope the crowd is as enthusiastic to see her as I am.

Mitski’s amazingly raw live performance is complete with choreographed dance moves, knee pads (yes, really) and full out shred sessions on her electric guitar – inevitably going to make this set one not to miss at Lollapalooza this year. Fingers crossed we get an after show from her, too! Click here to read my review on her stop in Chicago last October.

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Sharon Van Etten

Genre: Indie Rock
For Fans Of:

I’ve known the name Sharon Van Etten for years but as I always say, there’s so many artists you try to remember to listen to but fail to do so when you get distracted by someone or something else (or is that just me?)

Sharon Van Etten’s 2019 release, Remind Me Tomorrow, is another album on this list that received widespread acclaim – it was also her first release after five years. In between albums, she not only graduated from college with a degree in psychology, but she also had a role in the Netflix television show “The OA” and gave birth to her first child in 2017.

Remind Me Tomorrow was also Van Etten’s first album produced by John Congleton, an award-winning producer who has worked with artists like Lana Del Rey and St. Vincent – so it probably makes sense why I prefer this album over some of the earlier work I’ve heard of hers.

Van Etten just wrapped up a headlining tour earlier this year and had two stops in Chicago at Thalia Hall – I was sad to miss the show. Fortunately she’ll be back at Lollapalooza and I’m curious to see what sort of audience she pulls.

Headliners I plan to see on Sunday: Ariana Grande. Of course.

Subs: Kacey Musgraves

Thanks so much for reading! This post is always a big load to take on every year and it’s taken me days to work on and finish. I hope this leads you to new music to love!

  • Kristin

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