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PopTara’s Guide to Lollapalooza – The Acts You MUST See

Tara Bolar | Posted on March 31, 2019

The Acts You MUST See:

On March 20, Lollapalooza announced the lineup for their four-day annual outdoor music festival in Chicago. While the lineup offers some big names that I am beyond excited for such as, Ariana Grande, Childish Gambino, Janelle Monáe, and Tame Impala, there are some lesser known names that make dropping $402 on tickets worth it.

As we all should know by now, I, PopTara, have the absolute expertise on good fresh music, so trust me when I say these are the performances you’re not going to want to miss out on.

Kacey Musgraves

Kacey Musgraves – This year’s album of the year Grammy Awards winner, Kacey Musgraves is a must see at Lolla. The pop country singer, who recently went on tour with Harry Styles, provides a strange but soothing mixture of disco and yeehaw into her current music. Musgraves refreshing underdog-spirit is sure to give the gays everything they want and more. Top Songs: High Horse / Velvet Elvis / Lonely Weekend

Harry Hudson

Harry Hudson – Harry Hudson, my sweet yeehaw prince, is by far the act I am the most excited to see. Hudson’s sound can best be described as western-pop with R&B influence. Every Hudson show I have attended has always been nothing but genuine, energetic, and simply fun. Hudson, who is a cancer survivor, a fighter, and an optimistic, always makes his audience feel at home and if ya’ll don’t go see his set at Lollapalooza, you are going to jail. Top Songs: Kelsey / Just Slide (ft. Jaden Smith) / Quarter Life Crisis

Maggie Rogers

Maggie Rogers – Maggie Rogers has quickly become a need-to-know alt-pop star with the release of her 2019 debut album, Heard It In A Past Life. With a sound of lightheaded euphoria and precise lyrics, Rogers is an artist to groove to and chill out with at Lollapalooza. Top Songs: Alaska / Burning / Retrograde

Conan Gray

Conan Gray – Hailing from a small town in Texas, Conan Gray rose to fame after trials of self-made Garageband pop. His soft heart-eyes sound and dreamy aesthetics gives listeners that feel-good teenage vibe. While also serving fresh pop anthems, Gray also brings in a LGBTQ perspective into the music scene. As someone who has been watching Gray’s musical growth from the beginning, I cannot wait to see him take over Lolla, and those who do not catch his set will truly be missing out. Top Songs: Crush Culture / Generation Why / The King

King Princess

King Princess – The young indie-pop singer, King Princess, offers sophistication and clarity within her work. Giving listeners queer love songs and soulful vocals, King Princess is a bit of a musical prodigy who is just getting started. Hazy guitars, infectious lyrics, and genuine emotion – this is an artist you’re not going to want to miss. Top Songs: Pussy Is God / Talia / 1950

Roy Blair

Roy Blair – Roy Blair has become a favorite among the ebois and has claimed his spot in the bedroom-pop scene. The California native offers relatable tracks with a bit of an edge that fit perfectly into the summer atmosphere, just in time for Lollapalooza szn. Top Songs: Dennis / Perfume / Alex


Mitski – The Japan native, Mitski, serves catchy indie rock and candid lyrics. The honesty heard within her music keeps the listeners pulled in, and makes for the perfect act to see for those trying to unwind at Lollapalooza. Top Songs: Nobody / A Horse Named Cold Air / Pink in the Night

Hayley Kiyoko

Hayley Kiyoko – Hayley Kiyoko, also referred to as the Lesbian Jesus by many, is a go-to act for those wanting a taste of good fresh pop. The former Disney actress gives us smooth vocals, attitude, and looks, and I cannot wait to pop off with her this summer. Top Songs: Girls Like Girls / Curious / Sleepover

Japanese Breakfast

Japanese Breakfast – Indie-pop seems to be a theme at Lollapalooza this year, and Japanese Breakfast is one of those indie-pop acts you don’t wanna miss. With an experimental mixture of melancholy and shimmer, Japanese Breakfast gives us songs about queer confessions, grief, and life. Top Songs: Boyish / Road Head / Everybody Wants to Love You


Yaeji – Looking to party at Lolla? Go see Yaeji! Through a sound of whispery dreamlike dancefloor bangers, Yaeji expresses self-reflection, cultural identity, and exploration. Perfect for the club, perfect for house parties, and perfect for Lollapalooza. Top Songs: raingurl / Feel It Out / passionfruit


Joji – Melancholic and soulful, Joji mixes folk, trap, and R&B to carve out his unique sound. Joji was originally known for internet memes, such as the Harlem Shake, but he now serves sultry late-night spiraling tracks. If you’re going to Lollapalooza this year but also going through a heartbreak, Joji is the perfect act for you. Top Songs: Will He / YEAH RIGHT / SLOW DANCING IN THE DARK

Boy Pablo

Boy Pablo – Boy Pablo gives a good feel of bedroom pop and idie-rock to listeners. New to the spotlight, the band creates their sound with charming lo-fi production, relatable lyrics, and plenty of guitar riffs. With their sunny tones, Boy Pablo is a great group to see for those who want the true summer music festival feel. Top Songs: Feeling Lonely / Sick Feeling / Everytime

Tierra Whack

Tierra Whack – Tierra Whack is an artist who has everyone talking at the moment. Her theatrical and unique approach to rap and hip-hop has gotten the praise and attention it deserves. Through imaginative lyrics and an authentic sound, Tierra Whack has created a funhouse with her music, and everyone HAS to see her performance at Lolla. Top Songs: Only Child / Unemployed / Wasteland

Bea Miller

Bea Miller -Bea Miller is a go to for pop enthusiasts attending Lolla this summer. Her soulful yet glossy vocals got her all the way to 9th place on season two of X Factor, and since then the young popstar has released two official albums. Bea Miller is a perfect example of fresh and fun classic pop, mixed with quality lyrics and production. Top Songs: it’s not u it’s me (ft. 6lack) / burning bridges / bored

Ryan Beatty

Ryan Beatty – The former Radio Disney star, Ryan Beatty, has currently made his breakthrough in the pop scene. His debut album, Boy in Jeans, is a beautifully put together piece that tells the story of honest love and heartbreak. Beatty, another LGBTQ voice this year at Lolla, provides lush vocals and meaningful lyrics in all of his works, and this is an act I personally cannot wait to see. Top Songs: Party’s Over / God in Jeans / Cupid / God in Jeans again because it really is one of those songs EVERYONE needs to listen to


Bulow – Though new to the pop scene, Bulow has already proven herself to be a true artist on the rise with a promising future. With a bit of an edge in her songwriting and clean vocals, Bulow is a great act to catch early on in the day. Top Songs: Honor Roll / Not A Love Song / You & Jennifer

Tayla Parx

Tayla Parx – The songwriter behind Ariana Grande’s hit singles, Thank U Next and 7 Rings, Tayla Parx, is ready to take over Lollapalooza. The pop/R&B singer often incorporates feminism, gender, and an unique perspective into her music. With a sugary aesthetic and a whole lot of talent, Tayla Parx is a perfect act for Lolla.

If you want to get more familiar with these super sick recommended Lollapalooza acts, here is a playlist with their top tracks:

My name is Tara and I put out articles for UIC Radio on whatever day I can. I’m a media communication and professional writing major at the University of Illinois at Chicago. I host a pop music show, PopTara, on UIC Radio every Wednesday from 8:30pm-10:30pm. If you want to keep up with my saucy life you can follow me here:

twitter – @phemebot

music instagram – @lyricsbytara

personal instagram@tarapheme

facebook – @PopTara

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