Allen signed a publishing deal with Wide Open Music, a songwriting imprint formed by singer-songwriter
Ash Bowers, in 2016. Similarly,
Rolling Stone Country writer Brittney McKenna compared Allen's
contemporary R&B influences to those artists and
Maren Morris. Allen said that the song's title and central theme were inspired by his grandmother and his son, who was 4 at the time of the song's release. "Best Shot" was a Number One hit on the
Billboard Country Airplay chart in November 2018, making him the first Black artist to send his debut single to the top of that chart. The album's second single, "
Make Me Want To" released to country radio on February 1, 2019, and it also became a Number One hit on the
Billboard Country Airplay chart. Allen also recorded a cover of
Lady Gaga and
Bradley Cooper's "
Shallow" with
Abby Anderson in May 2019. The recording was made into a video as well. In 2020, Allen released "This Is Us", a duet with
Noah Cyrus. It was included on his new EP,
Bettie James, which was released on July 10, 2020. The project's second single was "Freedom Was a Highway," a duet with
Brad Paisley, which was released on February 1, 2021. It became Allen's third Number One hit and Paisley's twentieth on the
Billboard Country Airplay in February 2022. Allen became the first Black solo performer to win New Male Artist of the Year at the
2021 ACM Awards (at which he also performed a duet with
Brad Paisley). In September 2021, Allen was announced as one of the celebrities competing on
season 30 of
Dancing with the Stars. He and his partner Emma Slater were the ninth couple to be eliminated, ultimately placing 7th. On November 10, 2021, he won New Artist of the Year at the
CMA Awards. 15 days later, he performed at the
Macy's Thanksgiving Day Parade. In February 2022, Allen announced that he would be a guest mentor on
American Idol (season 20). He also featured on
Noah Schnacky's "Don't You Wanna Know" for his 2022 album
Thoughtfully Reckless and a duet with
Nick Carter in "Easy". Allen release the lead-off single, "Down Home," to his third studio album
Tulip Drive on March 8, 2022. The album was released on June 24, 2022. In 2023, Allen was a coach and judge on
My Kind of Country. ==Personal life==