Lollapalooza 2019: Best To Worst And Everything In Between

It feels like every year when I sit down to write this post, it’s been about five minutes since I wrote the last one. Funny how when my friends and I walked into Grant Park for the first time on Thursday afternoon, we joked that it felt like we had never left.

Time doesn’t seem to really move when you’re at Lollapalooza: there’s designated spots for everything like you’re at home in a little town for four days in the middle of Chicago. You learn (or re-learn) where the bathrooms are, where to get the good food deals – and of course where the alcohol is located (there are more bars in Lollapalooza than water stations).

All throughout today (Monday evening) I was relating the time to what set I had been at the day prior at said time (right now: it’s 10:23pm. I was on my way home post Ariana Grande). It’s a weird world where it feels like people abandon any sense at all and embrace being belligerent, carefree and sometimes forgetful of the importance of wearing sunscreen and staying hydrated (I’m not THIS cynical all the time, I promise).

Regardless of the TON of things to be annoyed about at a festival – especially this one – one that has undergone such immense transformation in the past 10 or so years – I saw some of the best performances I’ve ever seen ever this weekend, which gives me hope that the future of the festival.

On the other hand…feeling the urge to yell at every teenager who bumps into you is also a constant reminder every year I return over the age of 20 that I am no longer the fest’s target demographic and things like overcrowded areas annoy and stress the heck out of me. This year I felt it more than ever and it was a nagging feeling in the back of my head as I continuously told myself this was the last year I would be attending for four days.

I still feel that way but I also love the festival and how many incredible memories it’s given me since I was 19 years old (crazy how long it’s been). I will continue to be a fan but more from afar as it’s natural to grow up and away from anything. I love that I’m speaking about a festival like it’s my first born child. I digress.

I’ve done Lolla recaps every year for the past few years and wanted to try something a bit different this time around. Like I mentioned above, there were some artists who gave the best performances I’ve ever seen, and that deserves some sort of extra mention, right? I also had a lot of opinions on artists that I was not so impressed with, more intense opinions compared to how I’ve felt about artists I’ve seen at the festival in the past. I’ve split up the artists I saw into four categories.

  • Top Tier: Some of the best I’ve ever seen. Must see artists of the weekend.
  • Good: I enjoyed their sets but wasn’t necessarily blown away, “OMG” level.
  • Average: Not bad, but nothing I was overly thrilled about. Some artists who I expected more from are under this one. Artists who I think who will continue to grow into bigger careers with more experience are in this category.
  • Skip: Artists I will never see again.

Top Tier

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Childish Gambino

  • This was my FOURTH time seeing Gambino – all of those times I had seen him previously at a festival – and although I was curious to see how his show would be now that his catalog features a lot more R&B than it did when I had seen him previously, I was just as into it. There’s something incredibly magnetic about the way Donald Glover contorts and twists his face into expressions of mania and shock value that I’ve never seen before – like he’s telling you to look at him with your eyes as wide as they can get so you don’t miss anything important. It was hard to look away from the stage during his entire performance because I was just waiting for the next moment to be something crazy: and it really was unlike anything else I had seen before.

H.E.R.

  • While this was a time in the day on Thursday that I was considering seeing a few different sets, I am SO SO SO happy that I chose to see H.E.R. over anyone else. I was absolutely captivated by her performance and stage presence from start to end. It didn’t even matter that I wasn’t entirely familiar with her catalog – I went into it knowing maybe five songs and it felt like I had been listening to her music for years. It takes a special musician to be able to make someone feel like that. I think it’s wild that there were people in Grant Park during this performance who weren’t there. It was that incredible. I would absolutely go see her again at her own show in a heartbeat. BY THE WAY – she’s only 22 and has two Grammys.

Hozier

  • I would be lying to my readers if I told you that I haven’t been preparing to see Hozier live for the past six years. It’s the TRUTH! The only time I’ve been able to experience Hozier live was way back in 2014 when he performed three songs at JBTV – the music studio where I interned as a freshman in college. Honestly, that experience didn’t even come close to seeing him perform an entire set with his band. Seeing Hozier was like an out of body experience and was as close to seeing or believing in a real life Jesus that I will ever have and I am being dramatic but I MEAN IT. The second he walked onstage it was like a presence I had never experienced: his vocals never wavered, not once. He sounds better than he does recorded, which is a sentence I’ve said about less than five people ever, I think. He absolutely exceeded my expectations in every way possible and it was even more amazing when Maggie Rogers joined him onstage to sing “Work Song.” I cannot wait to see him again at the Chicago Theater this fall.

 

Jade Bird

  • I skipped Jade Bird’s actual set at Lollapalooza on Saturday to see Bad Suns finally make a debut at Lolla – but I only did this because I discovered she would be performing in the Toyota Music Den later that evening. I showed up about 7 minutes before she was scheduled for her 30 minute set (her actual set on the American Eagle Stage was 40 minutes) and the small area under a secluded tent was already starting to fill up and overflow into the grass. Jade was everything I expected her to be: powerful vocalist and skilled guitarist but continuously shocked as the crowd sang her lyrics back to her. “You’re going to make me cry,” she said towards the end of the set when the applause was so overwhelming it was bleeding into her performance time.  She still played two more songs after that, though!

Janelle Monáe

  • While I went into this performance knowing Janelle was going to be phenomenal, she exceeded all of my expectations and I will now hold all main stage performers to the a standard at Janelle’s level. The way she performs is unlike something I have never seen before and that is a rarity at a festival: costume changes, props, backup dancers, she has it all. Sure, there’s plenty of time and space for performers who go onstage with (or without) an instrument and just sing their hearts out – but it’s something entirely different to see a woman – and a woman of color at that – captivate an audience in such a way. Janelle was the perfect balance of cynical, critical and hopeful – and ending her set with a plead to “impeach Donald Trump” definitely made it even better.

Maggie Rogers

  • While I think Maggie is incredible and my history of being a fan of hers for the past three years definitely influenced where her set ended up in my rankings, she definitely teeters on the edge of good and top tier. I say this out of love and love only: she’s skyrocketed to such fame and acclaim over the past 18 months or so that it will continue for her to take time growing her vocals and stage presence to a spot that I think the others have surpassed her at this point. She definitely drew one of the biggest and most enthusiastic crowds I was apart of at Lolla over the weekend and it was so lovely to see other fans in this space. I have seen her three times now and this was the first time I got to see her after her full length debut was released and hearing some of those songs was very cathartic for me. Because of these feelings, she absolutely belongs in the top for me. I can’t wait to see where she goes next!

Mitski

  • It took all weekend to get to Mitski’s set. Out of the three I was most excited to see all weekend across four days, her’s was the last – and it was worth the wait. I got to the American Eagle stage about 8 minutes before her 7:45PM slot and immediately saw her sound checking onstage and I felt like a giddy teenager! Not only did Mitski deliver my favorite album of 2018, but I’ve continued to listen to it since I last saw her live (October 2018) and the album has continue to become very special and important to me. Knowing she’s on her way to taking a very long, possibly indefinite (unlikely) break in her career, this felt like a very special performance and a goodbye of sorts. Her crowd seemed to fill up eventually but I wish I could have seen her at a bigger stage earlier in the day to see who would have shown up. Since Kacey Musgraves’ performance ended one hour prior to Ariana’s (both on the same stage), I think a ton of people just stayed on that end of the park. Mitski –  if you ever read this – “Geyser” into “Townie” into “Nobody” was absolute perfection.

Good

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Bad Suns 

  • I never really have anything negative to say about Bad Suns but it seemed like they may have thrived more on a bit of a smaller stage, especially for their debut at Lollapalooza. They always sound good, have good interactions with the audience, but it was coming off as a bit robotic and rehearsed at points. Nevertheless I enjoyed them per usual!

Kacey Musgraves 

  • I’m getting nitpicky at this point because when you continue to see and write about live music, you start to pickup on characteristics you like and dislike about a musician. For instance, Kacey would NOT stop playing with her hair onstage and was pretty expressionless. I’ve had discussions with a good friend of mine about this who is also a Kacey fan and is convinced she’s incredibly high when she performs, which is probably why she seems to be so calm onstage. Vocals great! Would definitely see her again. 

King Princess

  • Similar to what I said about Maggie, there are so many artists blowing up this year that are still getting used to what it means to be a performer, and that’s how I feel about King Princess. I would argue that she’s on the top end of this list solely because I find her energy fascinating and very mature for someone who is such a young age (20). I enjoyed her set and am STILL waiting for her debut to be released. Hopefully before 2019 ends.

Lennon Stella

  • Great vocals, you can see that she’s continuing to learn how to take control of the stage – another artist who was on a main stage early in the day and had a good crowd pull. May have been better on a smaller stage with more comfort to move around a stage size she’s used to performing on.

Lil Wayne

  • Holy smokes, was I surprised by Lil Wayne’s energy! Definitely better than a couple of the headliners I saw this weekend (you’ll see who soon enough) and drew a crowd bigger than some of the headliners as well. Really enjoyed what I saw of his set and was amazed to hear how many hits he really has accumulated over the years of his career.

Sam Fender

  • No complaints from me on Sam except I really think he could have done better on a smaller stage. He’s ALMOST there but not quite just yet. HE’s touring a lot this fall and I’m sure it’ll be extremely beneficial for his stage presence.

Sharon Van Etten 

  • I only saw about 25 minutes of Sharon but she sounded absolutely incredible from where I was sitting. I would definitely need to take a deeper dive into her discography to feel like I can actually speak on her performance but from what I heard, it seemed like one long song with not much solid transitions between each, which to me, felt like it was hard for the audience to keep their attention on her set, especially when it’s at 5:30pm on the last day of the festival. I would love to see her own show, though.

Tierra Whack

  • You know if I’m going to see a rapper I must really like them or I have nobody else to see (I really like Tierra Whack). I was curious to see how her set would play out because her debut album was only 15 minutes long – 15 tracks at 1 minute each – plus a few singles she’s released this year that are full length. She started with said full length tracks and by the time I was heading over to see Maggie Rogers, she started playing the shorter ones. It was a different crowd since it wasn’t your typical “let’s go see this A-List rapper” crowd and it wasn’t your typical rapper. She’s interesting enough to hold a crowd’s attention and I would be curious to know what else she sang by the time I left.

Average

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Ariana Grande

  • Please don’t come for me for this…it’s how I feel! Ariana’s vocals were on point – no doubt about it – but she seemed really robotic and lifeless behind that vocal ability. I don’t blame her – she’s been incredibly outspoken about how much touring has affected her, and on top of having to cope with the bombing that happened at her concert two years ago after the country had two mass shootings overnight before her performance…I wouldn’t expect anyone to perform at their best after that. I was happy how great her voice sounded though and in regards to that she IS the real deal. I hope to see her recover from her anxiety she has as a touring musician soon because nobody deserves that.

Bea Miller

  • I watched Bea Miller way back in the day on the X-Factor and now she’s all grown up! Just kidding, she’s only 19. This is a tricky one because I definitely remember her having a ridiculous voice when she was a lot younger and I think it doesn’t seem as impressive anymore because she is not using it as much as she was back then. The style of music she is singing now is far more dance pop and doesn’t require her to really belt out notes a lot. That doesn’t mean she’s a bad singer, just different than what I expected.

Boy Pablo

  • I think I’m just getting incredibly old because every time an artist I was excited to see this weekend pulls a bigger crowd than I expect I’m shocked every time! This was true for Boy Pablo, whose 1:45pm set time on Friday afternoon pulled an insane amount of people. I really enjoyed his performance and was happy to see how much of a fanbase he really has. It’s hard for me to be able to tell what artists on the rise are really receiving buzz or if I’m just super excited about them, especially because I don’t have many friends who are as INTO music as I am.

Chelsea Cutler

  • Similar with Boy Pablo, I wasn’t sure what sort of crowd Chelsea Cutler was going to get. She ended up getting the 17-19 year olds of the festival and if I’m being totally honest, the crowd was really annoying and ended up affecting my experience. Regardless, Chelsea was impressive and I wasn’t sure what to expect from her, especially because I feel like she blew up out of nowhere.

Conan Grey

  • Conan Grey is just a little cutie pie and I was so excited to see his his first performance at a festival EVER! His music, songwriting and overall vibe reminds me a lot of early Troye Sivan and I can see why he has fans that gravitate towards him. He’s incredibly relatable, goofy and how I imagine the kids these days are in terms of personality. I loved his performance and know he’s going to get even better with more experience. He’s another performer who probably could have thrived more on a smaller stage, but still did really well with a large audience.

Harry Hudson

  • I was super interested in seeing what sort of performance Harry Hudson put on since I really enjoy his music and his vocal ability. However I felt like his performance left a lot more to offer and was hoping to see a bit more from him. He is also another artist who is just beginning to pull more of a following so I suspect he won’t have any issues continuing to grow. And his special guest appearance by Jaden Smith definitely helped some stragglers come check out the set.

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Hayley Kiyoko

  • I enjoy a handful of Hayley’s songs and think she’s a great person but I was really not impressed with her performance. Her vocals were subpar and overall the performance was a little bit boring. I would guess that my indifference towards her catalog would influence my opinion, but also it just felt a little lackluster. I’m calling it now that she’s Taylor Swift’s next tour opener. You heard it here first. 

Louis The Child

  • I don’t feel very qualified to critique a DJ’s live performance in any way to be quite honest but I left Louis The Child’s set fairly impressed! Although I heard that their crowd got super rowdy, the area I was chilling in was super casual and they put on a fun dance party. I’ve learned over the years that this is the sort of dance music I enjoy so it was a fun 30 minutes or so to just relax and dance. They definitely pulled one of the biggest crowds I saw for a mid afternoon performance all weekend.

Masego

  • I only half watched this for about 15 minutes so I don’t feel super obligated to say anything positive or negative, but Masego had fantastic stage presence and really knew how to draw the crowd in. His self-defined “TrapHouseJazz” music is interesting and I suggest you take a listen if you haven’t!

The Strokes

  • Any performer who is over 15 minutes late to their own headlining set already rub me the wrong way, so The Strokes had their work cut out for them when they started their set. I saw about 30 minutes of their performance and was pleasantly surprised with the amount of songs I recognized as I am not a super intense fan of the band. I can definitely see why they have such an intense fan base and their music really isn’t for me and neither is their live performance. I didn’t dislike it but it’s something I probably wouldn’t seek out again.

Shaq

  • Again with the “I’m not qualified to judge dance music” but this was more entertaining than anything. We took a sneak peek at Perry’s Stage solely to say “I saw Shaq do a DJ set at Lolla one year” and it seemed decent enough. From what we could tell, he was definitely doing the work live, which is more than what some of the artists on this list have to offer…more on that below.UPDATE: I’ve been informed by the Reddit community that Shaq barely did anything live. Can someone confirm or deny? I couldn’t really see from where I was but it seemed like he was actually performing and not pressing a button. 

Skip

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The Chainsmokers

  • We all have that background knowledge that The Chainsmokers are sort of hated in the EDM community for their lack of talent and that the ongoing joke is that they just press a button to play music at their sets. I was way too far away from the stage for the 30 minutes I saw them perform, but I would venture to assume that the rumors are true. Not only did the one dude (I googled it – his name is Drew Taggart) attempt to sing multiple times, but he’s absolutely terrible at singing. It was incredible to see someone who does NOT know how to sing try to sing as hard as he did. Either he doesn’t care or he’s very unaware. I have to admit that dancing to “Closer” was pretty fun – especially when the duo decided to randomly invite Isaac Slade of The Fray onstage to do a mashup with The Fray’s only memorable song, “Over My Head.” It turns out that he’s a co-writer on “Closer.” Who would have thought! Don’t waste your money on these dudes.

Judah & The Lion

  • Judah & The Lion are not bad performers, they are simply just not my cup of tea. If you don’t like music that is 95% screaming and references to “5th grade dances” and “my mama,” chances are you won’t like this band either. I have never gone into a performance with such ignorance for their music and hated it as much as I hated this performance. I hate saying this because a lot of my friends who attended love them but it was just not for me. At all.

Role Model

  • The lineup on Saturday was pretty weak for me, so there were a couple hours where I was just jumping around sets to waste my time. I caught about 15 minutes of Role Model – the newest internet sensation – and was not into it at all. I don’t like being critical – but he’s just another 21-year-old with a cute face and a ton of Instagram followers. I hope he proves me wrong in the future.

Twenty One Pilots

  • This one is particularly hard for me to write because I was a decently dedicated Twenty One Pilots fan from about 2014-2016. They have put out some great music and their live shows are very different to anything else that I was seeing a few years ago. But I think that’s the point – it was a few years ago. Their live show now consists of expressionless faces from Josh and Tyler, songs about constantly being considered underdogs and not wanting to give into the fame (haven’t they, though?) and this overall sense of “We are different and we are cool because of it look I’m wearing my shirt over my face while I play the ukulele and look I’m wearing big sunglasses on stage at 9pm” that it just felt incredibly contrived and overdone. I saw about five or six songs and would have left earlier if my friend wasn’t staying with me and wouldn’t have been able to find her way back home alone. I hate being negative in my writing and I don’t like feeling like I’m spreading a negative energy, but I was really not feeling this performance at all. I digress.

Final order of the 30 acts I saw, these are my most to least favorite:

  1. Janelle Monáe
  2. Childish Gambino
  3. Hozier
  4. Mitski
  5. H.E.R
  6. Jade Bird
  7. Maggie Rogers
  8. Kacey Musgraves
  9. Bad Suns
  10. Tierra Whack
  11. King Princess
  12. Lennon Stella
  13. Lil Wayne
  14. Sharon Van Etten
  15. Ariana Grande
  16. The Strokes
  17. Sam Fender
  18. Louis The Child
  19. Conan Grey
  20. Boy Pablo
  21. Chelsea Cutler
  22. Hayley Kiyoko
  23. Harry Hudson
  24. Bea Miller
  25. Masego
  26. Shaq
  27. Role Model
  28. Judah & The Lion
  29. Twenty One Pilots
  30. The Chainsmokers

There’s 4,000 words for you! Thanks for reading if you made it to the end. I hope you enjoyed it and if you attended the festival this year, I hope it treated you well. I keep saying I won’t be back next year for 4 days but honestly, we’ll see what happens.

Click here to read all of my previous Lollapalooza coverage.

  • Kristin
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