Another video, "Flaming Hot Cheetos", was released a month before "Pretty Girl" on YouTube. It garnered 3 million views by July 2018. The success of "Pretty Girl" led to interest from major labels such as Capitol, RCA, and Columbia. Jon Cohen, the co-founder of The Fader, signed Clairo to the magazine's associated record label with a 12-song record contract and introduced her to Pat Corcoran, manager of Chance the Rapper. She became a client of talent agency Haight Brand near the end of 2017.
In April 2020, Clairo revealed that she had begun working on her second studio album via a tweet of a screenshot of a playlist titled "Album 2 (demos so far)". Also in October 2020, she formed a new band called Shelly with indie pop artist Claud and their two friends from Syracuse University, Josh Mehling and Noa Frances Getzug. The group released two songs, "Steeeam" and "Natural", on October 30, 2020.
On June 11, 2021, Clairo released "Blouse", the first single from her second studio album, Sling, which was announced on the same day. The record is for Clairo, but it is also a record of her attempts to reevaluate her goals in life, bearing the Laurel Canyon imprint and replaces Immunity's sparse electronic flourishes with lush, acoustic folk frequently adorned with swooning vocal harmonies, delicate strings, and the warm swell of brass. It was released on July 16, 2021, and was praised for Clairo's artistic progression and thematic songwriting that ponders future motherhood, domesticity and the responsibility of becoming a caregiver. It appeared on numerous "best albums of 2021" lists.
In February 2022, Clairo embarked on the US leg of the Sling tour. She canceled the last three dates of her North American tour, after a technical incident at her gig in Toronto left her with temporary hearing damage. After two songs, her opening show of the UK tour in Bristol had to be canceled due to a case of sinusitis that was affecting her voice, leading to her having a panic attack onstage and leaving afterward. The Glasgow show was canceled but the show the day after it in Manchester went ahead, and her final UK show of that tour was in London.
On August 4, the music video for "Juna" was released. It marked Clairo's first music video in six years, and it is wrestling-themed. The next day, she released a cover of Lana Del Rey's "Brooklyn Baby" exclusively on Spotify as part of the Spotify Singles series. On October 9, Clairo released a cover of singer-songwriter Margo Guryan's "Love Songs". The cover song is a part of the Guryan tribute compilation album Like Someone I Know, released on November 8, 2024. Simultaneously, Charm was nominated in the Best Alternative Music Album category of the 67th Annual Grammy Awards. This marked Clairo's first Grammy nomination.
On December 3, Clairo shared the music video for "Sexy to Someone". On February 6, 2025, a music video for "Terrapin" was released. It was directed by actress Ayo Edebiri, and features "Weird Al" Yankovic as "Clairo".
After the success of "Pretty Girl", a number of social media users (specifically on discussion website Reddit) began claiming that Clairo was an "industry plant" who gained success through her father's nepotism. She denied the claims, calling them sexist. Writers for The Guardian and The Ringer also stated that her father's connections facilitated their record contract signing.
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