He felt both creatively and emotionally constrained by his image as a "straight" teen heartthrob and the lack of input he was allowed when he was recording music.

I don't want this to sound like I regret anything, but it's really difficult.In 2013, he opted to fire his initial management team only a little over a year after his quick rise to recognition had begun.

[9] In a 2020 interview with The Guardian, Beatty recalled firing his manager on a plane flying back to Los Angeles after a gig and telling them, "I can't do this anymore.

[13] That same year, he also collaborated with rapper Tyler, the Creator on his EP Music Inspired by Illumination & Dr. Seuss' The Grinch and producer Benny Blanco on his album Friends Keep Secrets.

Additionally, he performed with Brockhampton on The Tonight Show Starring Jimmy Fallon, alongside Jazmine Sullivan and serpentwithfeet, singing backing vocals on an early version of the song "Tonya" which later appeared on their album Iridescence.

Starting in January 2019, Beatty embarked on a short tour in support of his album Boy in Jeans, first with shows in Los Angeles and Brooklyn and then continuing in March with a West Coast tour with shows in Seattle, Portland, San Francisco, San Diego, and Los Angeles.

[14][15] In a 2020 interview with Complex magazine, he said that he initially delayed touring after the release of Boy in Jeans to focus on recording his second album, Dreaming of David.

Soon afterwards, he announced a US tour called "David, I Love You" in support of the album, though this was later cancelled due to the social distancing measures taken in response to the COVID-19 pandemic.

[19] He was also featured alongside Dua Lipa and Jon B in the remix of "Sugar", released in March 2020, which included an additional solo verse for Beatty not in the original version.

[22][23] On March 15, after a series of Instagram posts and the launch of his new website, Beatty announced his third studio album, Calico, would be released April 28, 2023.

[28] Calico was well received with critics calling the album "a transformative step for the visionary singer-songwriter, an intimate and admirable embrace" and "arguably his best work to date.

[32][non-primary source needed] The tour ran from September 13 to 23, with the international leg being canceled in early October due to logistical issues.

"[11] In May 2020, Beatty expressed support for the Black Lives Matter movement in the wake of national outrage in response to the murder of George Floyd by Minnesota police officer Derek Chauvin.