The Chicago High School for the Arts hosted a homecoming this week for R&B singer Ravyn Lenae, who was once a student with promising talent and big dreams at the West Town school.
A flood of memories washed over the 2017 graduate as she toured the halls Wednesday. She pointed out the classroom where she took driver’s ed, the large ensemble room where she rehearsed and even her old locker that she would leave unlocked because she could never remember the code.
“This is so special,” she gushed.
It was special for current students and alumni, too, as they filed into the Black Box Theatre to attend a Q&A with Lenae. Set to make her Lollapalooza debut Friday, the South Side native is enjoying a period of success marked by a top 10 hit with “Love Me Not” and a fall tour opening for Sabrina Carpenter and Renee Rapp.
Since signing her deal with Atlantic Records at 17, Lenae has recorded several EPs and two full-length albums. She has collaborated with Steve Lacy, Childish Gambino and Kaytranada. She credits ChiArts with preparing her not only vocally and creatively, but also training her to handle the business and day-to-day grind of being an artist.
“I feel like I have an upper hand with touring and just performing rigorously,” said Lenae, now 26. “I’ve never had a voice issue while touring, and I think that is due to really understanding how my voice works and having to use it in certain ways.”
The arts training, which included vocal lessons each Saturday, helped her develop work ethic, she said.
“The schedule alone is something that you have to commit to,” she said. “So having to make that decision over and over that this is something that you really want to dedicate your life to is something I learned by going here.”
Lenae commuted from her home in West Pullman to the public, tuition-free school, which she said opened up new opportunities.
“Chicago as a city can feel really segregated,” she said. “I got to see so many different parts of the city that I had never seen before. And with that, being able to meet so many different types of people from the city that I may have never crossed paths with.”
Outside of school, Lenae developed her talent in the choir at Pullman Christian Reformed Church, where her grandfather served as pastor. She also built a buzz recording at Classick Studios in Humboldt Park and uploading music to SoundCloud.
“I was a menace,” she recalled, laughing. “When I would drop, I would send it to every single person in my contact list.”
Lenae also won a contest to headline at House of Blues Chicago, where Atlantic Records staffers showed up.
The ChiArts students listened intently as Lenae recounted her journey, and they asked thoughtful questions about her artistic process, influences and perseverance in the industry. Some even stayed to record a TikTok dance with the singer.
“I’m a big fan of Ravyn because I like the message that she stands for, and I like how vulnerable she is in her music,” said Lavontae Alexander, an 18-year-old singer who graduated from ChiArts this year.
Alexander also said he was inspired to see another Chicagoan achieve their dreams.
“It helps me know that I can also go far in life and maybe be in the [Billboard] Top 10,” he said.
Though “Love Me Not” was released in 2024, it has recently gained traction after going viral on TikTok. And everyone from music writers to Spotify editors have placed it in the running for this year’s “song of the summer.”
“Once I finished the song and my team heard it, everybody felt the same amount of magic around it,” Lenae said. “I think we all knew that it had the potential to blow up. Better late than never. And I know things happen in divine timing.”
Lenae cast her family members in the video, which was filmed at her grandmother’s house in West Pullman. She said the visual, along with her recent album, “Bird’s Eye,” is about exploring what defines her as a person.
“A lot of that meant coming back home to Chicago, walking through the house I was raised in, going through each room and remembering who I was in each of them,” she said.
And returning to the city to play Lollapalooza is an indicator of how far she has come.
“Lollapalooza always meant you made it to me,” she said. “I dreamt about myself being in that position. So this is a full-circle moment for me, and I think it’s going to be a memorable one.”