This summer, Grant Park hosted Lollapalooza, marking the 20th anniversary since the festival decided to make Chicago its permanent flagship home. Taking place from Jul. 31 to Aug. 3, almost 400,000 fans packed the park until midnight for four days in a row, and the energy was electric. Multiple high-profile musical acts took the stage as some of the eight headliners, with genres ranging from everything from EDM and hip-hop to rock and roll and bedroom pop. While ‘Lolla’ is a massive deal to any artist, as many plan rollouts, tours, and merch drops to coincide with the festival, it’s equally worth checking out the past year from some of these major headliners, and seeing where they’ll be heading next in the coming months.

Olivia Rodrigo

Coming off the success of her latest album “Guts”, Olivia Rodrigo headlined on Friday, Aug. 1. Rodrigo has recently concluded her coinciding Guts World Tour, which began Feb. 2024, and concluded after 102 shows on the first of July this year. Many praised Rodrigo’s blending of her signature pop style with more rock elements, introducing a classic genre to a younger audience. Rodrigo’s numerous openers also received similar acclaim, including one Chappell Roan, whose 2024 Lolla performance set the record for the largest daytime set attendance in the festival’s history. Rodrigo also brought along some massive names as guest performers during her main set, including Noah Kahan, Robert Smith of British band The Cure, and Ed Sheeran. During her headlining set, Rodrigo performed from both of her albums, as well as performed select Weezer songs with the band themselves, whom she brought out as guests. With the conclusion of her world tour, many are suspecting that a new era, and associated album, can be on the horizon, with Rodrigo shifting to a new red motif on her website, and wearing a “3” shirt to her Oshega Festival performance.

Tyler, The Creator

More so than many fellow headliners, Tyler, The Creator, whose birth name is Tyler Okonma, has had a busy year. After being mostly silent for the better part of a year following the release of his album “The Estate Sale” in 2023, sticking to mainly fashion ventures with his GOLF Le FLEUR* brand, Okonma shocked the world with the surprise drop of his album “Chromakopia” on a random Monday in October 2024, after less than a week of promotion.  After the initial success of the album, Okonma embarked on the 96-show Chromakopia: The World Tour, spanning the United States, Europe, and Oceania. While on the tour, Tyler surprised his fans for the second time in less than a year, releasing his 28-minute long dance album “Don’t Tap The Glass” in July of this year. The album became a viral sensation, with tracks like “Sugar On My Tongue” and “Ring Ring Ring” blowing up and being praised as songs of the summer. Tyler has been hard at work for the past year, and after Lollapalooza, many suspect he’ll take a long step back from music, and delve further into fashion, with his collaborations with Louis Vuitton and Converse.

Sabrina Carpenter

For more than a year now, Carpenter has been one of the hottest up-and-coming names in the pop industry. Since the release of “Espresso” in April 2024, and her album “Short ‘n Sweet” dropping in August of the same year, Carpenter has been on a generational run, winning 2 Grammys and 6 nominations at the 67th Annual Grammy Awards, and embarking on the highly-successful Short n’ Sweet Tour to round off her year. With so much hype around the name, many were looking forward to the year she’d have in 2025, and fans were not left disappointed. Carpenter released the single “Manchild” in June of this year, marking her first No. 1 debut on the Billboard Hot 100 chart. With this momentum, Carpenter kicked off the rollout of her seventh studio album “Man’s Best Friend”, which ended up releasing after her headlining Lolla set, occurring on August 3rd. The album, while slightly controversial, enjoyed wide critical acclaim, and debuted on top of Billboard’s Top 200 chart, selling over 366,000 album-equivalent units in its first week. This marks the third highest selling week for an album in 2025, and the highest selling week for an album by a female artist this year.

A$AP Rocky

While having a rather quiet year musically, A$AP Rocky, born Rakim Mayers, has launched multiple successful ventures in different assortments of media. Mayers, one of the sharpest dressers in the rap game, has had his eyes on the fashion industry for a long time, and has very recently launched his own dedicated runway shows through his brand AWGE. His most recent show, Obligatory Fashion, took place in this year’s Paris Fashion Week Men’s. Mayers has always been a cultivator with a unique style, blurring the lines between streetwear and high fashion, and this show demonstrates this unparalleled matching perfectly; pairings included blazers, dress pants, and dresses meeting layered denim jeans, ski masks, and shirts with slogans such as “Stop Snitching,” “Don’t Be Dumb,” or “American Sabotage”. Mayers has also taken a step into the world of film, co-starring with veteran actor Denzel Washington in A24’s “Highest 2 Lowest”, a Spike Lee-directed film which received much critical acclaim. With so much going on in every other aspect of Mayers’ life, it truly seems like the music has taken a step into the background in terms of his priorities. Mayers hasn’t professionally released an album in almost seven years, with his last release, “Testing”, suffering mixed reviews from critics. While Mayers has released a few singles in the past few years, including the popular tracks “Highjack” and “Tailor Swif”, there’s no promise of an album anytime soon. His rumored project “Don’t Be Dumb” was meant to drop Aug. 30 of 2024, and now, more than a year later, the album doesn’t seem any closer. Ultimately, despite snippet releases and festival debuts, it may be a while before we hear any new albums from Mayers.