| 2007 | Finished seventh on season five of USA Network's Nashville Star, her first major national television exposure as a teenage singer-songwriter from Golden, Texas. |
| 2012 | Co-wrote Miranda Lambert's 'Mama's Broken Heart,' ranked number 26 on Rolling Stone's 50 Best Singles of 2011, before signing with Mercury Nashville and issuing the debut single 'Merry Go Round.' |
| 2013 | Dropped debut album 'Same Trailer Different Park,' channeling influences from Loretta Lynn and John Prine alongside Cake and The Beach Boys into a country voice unlike anything else on Nashville radio, earning the Grammy for Best Country Album. |
| 2015 | Put out 'Pageant Material,' building on her debut with the single 'Biscuits' while opening for Willie Nelson and Lady Antebellum across North America and Europe. |
| 2018 | Released 'Golden Hour,' named Best Album of 2018 by Time, Billboard, and Rolling Stone, taking home the Grammy Award for Album of the Year and Best Country Album at the 61st Annual Grammy Awards. |
| 2021 | Unveiled 'star-crossed,' a breakup album that debuted at number one on Billboard's Top Album Sales chart; the Recording Academy ruled it ineligible for country classification and placed it in the pop vocal album category. |
| 2023 | Featured on Zach Bryan's 'I Remember Everything,' the first country duet to top the Billboard Hot 100 in 40 years; the track won Best Country Duo/Group Performance at the 66th Annual Grammy Awards in February 2024, her seventh career Grammy. |
| 2024 | Issued her sixth studio album 'Deeper Well' on March 15 via MCA Nashville, debuting at number two on the Billboard 200, then headlined the Deeper Well World Tour from April through December across North America, Europe, and Australia. |
| 2025 | 'The Architect,' a Deeper Well single written in response to the 2023 Nashville school shooting, won Best Country Song at the 67th Annual Grammy Awards on February 2, 2025, bringing her career total to eight Grammy wins. |
| 2026 | Scored a triple Billboard chart debut with 'Middle of Nowhere,' her seventh studio album released May 1 on Lost Highway Records, topping Top Album Sales, Vinyl Albums, and Indie Store Album Sales while landing at number three on the Billboard 200 with 100,000 album-equivalent units, her best first-week sales. |