Pick a Day

Chappell Roan is born Kayleigh Rose Amstutz in Willard, Missouri. Growing up, she yearns to escape the confines of her conservative Christian household and finds an outlet in music. In honor of her grandfather Dennis K. Chappell, who is one of her biggest supporters, she creates her stage name by combining his last name with his favorite country tune, "The Strawberry Roan" by Curley Fletcher. Her 2023 debut album, The Rise And Fall Of A Midwest Princess, is a bold exploration of her sexuality that cements her status as a bonafide pop star.

Chappell Roan releases her debut album, The Rise And Fall of A Midwest Princess, which chronicles the Missouri-born pop singer's journey of self-discovery as a queer artist on tunes like "Femininomenon," "Red Wine Supernova," and "Pink Pony Club." The latter, the story of a small-town girl who fulfills her dreams as a go-go dancer in LA, mirrors her own teenage fantasies of escaping her conservative hometown. The album is a sleeper hit, taking nearly a year to reach its peak position of #2 on the Billboard 200 albums chart.

Chappell Roan makes her Saturday Night Live debut, where she introduces her first country song, "The Giver," which subverts the genre's traditional imagery with a queer twist. Roan, who also performs her disco-pop hit "Pink Pony Club" on the SNL stage, grew up strictly listening to Christian and country music until Lady Gaga's "Alejandro" turned her on to pop. She clarifies her foray into country is just for fun and not a permanent genre shift.

Miley Cyrus revisits Hannah Montana for a Disney+ 20th anniversary special. Former cast members, along with stars like Selena Gomez and Chappell Roan, join Cyrus in sharing memories of the show, which ran from 2006 to 2011 and starred Cyrus as a schoolgirl who was secretly a rock star. Cyrus debuts a new song on the special called "Younger You," written in the form of a letter from her younger self.

Olivia Rodrigo hosts the Daisy Chain Fields festival at Great Park in Irvine, California. Inspired by Lilith Fair, the singer leads an all-female lineup that includes Chappell Roan, Mitski, Garbage, and Bikini Kill, along with special guests Alanis Morissette, Stevie Nicks, and Lilith Fair co-founder Sarah McLachlan. The event raises $20 million for charities supporting women's issues and labor rights.More