He was inspired by the country music his father listened to, particularly Merle Haggard, as well as an Elvis impersonator he saw sing at a nearby restaurant.

He ended up landing the part, which required him to move from Texas to Nashville, Tennessee, during his senior year of high school.

"I decided that I wasn't quite ready for that platform yet, and that it would be a better step for me to move to Nashville and focus on my music first," he said.

Milligan and his band appeared on America's Got Talent on June 8, 2022, receiving four "yes" votes for his performance of an original song, "Sounds Like Something I'd Do".

Drake and his band made a special appearance on an AGT's Results Night, September 13, 2023, performing his new single, "I Got A Problem".