Olivia Rodrigo and Chappell Roan are two of the most exciting pop stars of their generation, but their connection is far from a superficial industry friendship. They share a deep bond that started before either was a household name, and every turn in their careers seems to pull them closer together. If you've caught glimpses of them supporting each other on social media, at concerts, or on red carpets, you've likely wondered exactly how this friendship began. Let's rewind and trace their journey from early LA days to festival main stages.
Early Days in Los Angeles
Chappell Roan moved to Los Angeles around 2018, determined to carve out a name for herself in the music world. She soon began working with music producer Dan Nigro, a key creative force behind some of modern pop's most celebrated records. Around 2020, Dan started working with Olivia Rodrigo as well, creating a professional overlap that would eventually bring both singers into the same orbit. During those early years, Olivia would visit Chappell at a donut shop where the then-aspiring singer worked. Olivia has recounted how she used to go eat donuts with Chappell and simply hang out, long before Chappell dropped her debut album or Olivia became a global superstar. That simple, unpretentious beginning laid a foundation of mutual trust that neither stardom nor success has eroded.
2022: The SOUR Tour and Early Support
In January 2022, Chappell announced she would be joining Olivia on a date of the SOUR Tour. She took to social media to express her excitement, writing, "OMG I'M OPENING FOR @oliviarodrigo MAY 27 SAN FRANCISCO. I love u SO MUCH Olivia & I can't wait !!!! LETS GOOO" Olivia responded with equal enthusiasm, exclaiming "YASSSSS LOVE U." The gesture was a clear sign that their friendship had become a working alliance.
February brought another milestone when Olivia attended Chappell's birthday party. A photo from that night captured Chappell posing with Dan Nigro, Olivia, and Conan Gray, hinting at a tight-knit creative circle in which everyone genuinely celebrated one another. By May, Chappell took the stage as Olivia's support act for that San Francisco show and later penned a heartfelt Instagram caption reflecting on the experience. "This was fcking crazy. Thank you @oliviarodrigo for asking me to open. It was truly an honor. Your fans were the sweetest angels to me," she wrote. That same summer, in August, Olivia returned the favor by attending Chappell's headlining show at New York City's Bowery Ballroom. She looked overjoyed, dancing and singing along. Olivia and Conan even enthusiastically joined in on Chappell's "Hot to Go!" choreography, and the moments were captured on social media, much to the delight of fans who loved seeing these artists let loose and support each other.
As 2022 wound down, Chappell used her December recap post to shout out the female friends who had helped her through the year. Included was a snapshot of her with Olivia backstage at that NYC show. "This year has been a femininomenon," she wrote, a clever nod to her own song title, before thanking her friends for everything.
2023: Navigating Fame Together
By 2023, Chappell's star was rapidly rising, and she turned to Olivia for guidance on how to handle the pressures that come with growing visibility. In an interview with NYLON, Chappell opened up about her first-ever NYC Pride and the candid advice she received from Olivia. "When you were getting big, did you talk to Billie [Eilish]? What did you do?" Chappell asked her. Olivia's reply was honest and humanizing: "I don't have the answers — I'm sorry. No one has the answers." Chappell also praised Olivia's grounded nature: "She's so good at being a normal person when everything is abnormal around her." That vulnerability and authenticity defined their bond as both navigated fluctuating levels of fame.
In September 2023, Olivia announced her GUTS Tour, and Chappell soon revealed she would once again be hitting the road with her friend. Speaking to Triple J in November, Chappell expressed her gratitude for being asked to open again. "I've only played my first headline show last May, and to go from, like, 200 people to 20,000 in less than two years is very intense and fast," she said, acknowledging how monumental the opportunity felt.
December 2023 brought more reflections on fame. Chappell told The Independent she had asked Olivia if she had contacted Billie Eilish for advice on dealing with online bullying and the strange realities of becoming well-known. Olivia's response was "kind of sad," Chappell noted: "No one has it figured out. No one has the answer. It's different for every person." Still, hearing that from someone she respected helped Chappell feel less isolated. Around the same time, Olivia revealed that Chappell was her most-streamed artist on Spotify Wrapped. "She just put out her first album, and Dan, my producer, produced it, and it's amazing. So I'm listening to a lot of her," Olivia shared, adding that Simon & Garfunkel came in second on her list.
2024: Deeper Collaborations and Iconic Moments
January 2024 was packed with revelations. In a long-form interview about her debut album, The Rise and Fall of a Midwest Princess, Chappell confirmed she had contributed background vocals to Olivia's songs "Lacy," "Obsessed," and "Bad Idea, Right?" This behind-the-scenes collaboration underscored how intertwined their musical worlds had become — both were working with Dan Nigro, and Chappell was literally adding her voice to Olivia's records. Later that month, Chappell made a TikTok sharing fun facts about herself and her friendship with Olivia before the GUTS Tour and her own Midwest Princess Tour kicked off. "I love you, girl. I'm so excited to tour with you," she said in the clip, radiating genuine affection.
In March, Chappell spoke to Time and gushed about how Olivia handles criticism with grace. Then, in April, Chappell celebrated her last night on the GUTS Tour by surprising Olivia during a fan interaction segment. The surprise delighted the audience, and Olivia later posted a sweet film photo with Chappell on her Instagram Stories, capturing a tender moment between them.
That spring also produced one of the funniest anecdotes in their friendship. Because Chappell is known for her theatrical stage presence and drag-adjacent performance style, she was asked what Olivia's drag persona would be called. Chappell's answer: Sophia Rodriguez. "Everyone calls her Rodriguez instead of Rodrigo all the time," she explained, adding that Olivia had once told her she was almost named Sophia. The revelation gave fans a playful glimpse into these two pop stars discussing deeply personal trivia.
When August rolled around, Chappell joined Olivia for a surprise performance of "HOT TO GO!" during Olivia's GUTS World Tour stop in Los Angeles. The two also participated in a silly TikTok trend, with Olivia saying "I hope she plays 'HOT TO GO!'" and Chappell responding, "This is an Olivia Rodrigo concert, bitch." The energy was electric, and professional photographers captured high-octane moments from the duet as the crowd roared.
In October, Olivia elaborated on that surprise performance to Variety. "I certainly didn't have to learn 'Hot to Go!' I think that was actually one of my top five Spotify songs like two years ago," she admitted. She also revealed that the screams from the crowd when she introduced Chappell were the loudest she'd ever experienced. "People were so excited — I swear to God, they just screamed bloody murder for like six minutes. It was awesome." Olivia used the interview to emphasize how interconnected their careers have become. "She does background vocals on both of my albums. So we're very intertwined in each other's worlds," she stated.
The very next day after the GUTS World Tour film dropped, Olivia appeared on The Tonight Show Starring Jimmy Fallon and shared a touching memory that put their yearslong friendship in perspective. "I used to go visit her when she worked at a donut shop, before she got signed, before she put out any of her music. I used to just go eat donuts with her and hang out," Olivia revealed, delighting Fallon and the audience alike.
2024 Wrap-Up and 2025 Milestones
December 2024 brought yet another Spotify Wrapped moment. For the second consecutive year, Chappell topped Olivia's Wrapped list, this time with "Good Luck, Babe!" as her most-played song. Olivia posted her results to her Instagram Stories with the caption "I know that's right," tagging Chappell and Dan Nigro. It was a small but public declaration of ongoing mutual admiration.
The two reunited in February 2025 at the Grammy Awards. Olivia introduced Chappell as her "extraordinary friend" before Chappell delivered a historic performance of "Pink Pony Club" and took home the award for Best New Artist. The moment felt like a culmination of years of quiet support, with both artists now standing at the peak of the industry.
2025 and 2026: Festival Fun and Box-Office Pop
In July 2025, Liv, Chappell, Conan Gray, Madison Hu, and Addison Rae were all spotted attending Lady Gaga's Mayhem Ball concert at the Kia Forum in Los Angeles. The group night out signaled that the friendship was still going strong, now with a wider circle of famous friends.
June 2026 saw Olivia announce her historic Daisy Chain Fields music festival, an all-female bill featuring some of the most beloved artists in pop. Chappell was on that lineup, and Olivia wrote, "The lineup is truly insane and full of my heroes and friends." When the festival took place in August 2026, Chappell's performance was highly anticipated. She had been largely offstage since joining Noah Kahan for a surprise duet of "California" earlier that month, making her Daisy Chain Fields set a true event. Chappell later shared a moving Instagram recap post addressed to Olivia. "@oliviarodrigo u r so inspiring in so many ways. We need artists like u who use their platform for good and are such a light in the world," she wrote. Olivia responded with a flood of tears emojis, declaring, "u inspire me so much and I am so lucky to know u!"
The following month, the pair graced the cover of Rolling Stone alongside Sarah McLachlan and Doechii, with additional shots featuring Olivia and Chappell together in the same glossy spread. Seeing them side by side, both beaming with pride and camaraderie, it's hard not to feel pure happiness. Their friendship, once forged over donuts before either had a hit song, has become a masterclass in showing up for the people who make your world brighter.
Source:Cosmopolitan News