He gained mainstream recognition following the release of his 2015 single "Don't," which peaked at number 13 on the Billboard Hot 100 and received septuple platinum certification by the Recording Industry Association of America (RIAA).

Trapsoul received triple platinum certification by the RIAA and spawned the follow-up singles "Exchange"—which earned him a Grammy Award nomination—and "Sorry Not Sorry."

That same year, he guest featured alongside Rihanna on DJ Khaled's hit single "Wild Thoughts," which peaked at number two on the Billboard Hot 100.

[6] In 2013, Tiller had a child and took a break from music while working at Papa John's and UPS to provide for his daughter, Harley.

[7][8] In October 2014, Tiller uploaded his debut single "Don't" to his SoundCloud account, which started receiving some internet attention from music industry insiders.

[25] In May 2016, Tiller made his US television debut, performing "Exchange" on the Late Night with Seth Meyers show.

[27] In July 2016, DJ Khaled released his ninth studio album, Major Key, which includes the song "Ima Be Alright" featuring Tiller and rapper Future.

[29] In January 2017, he was included in Forbes magazine's "30 Under 30", a list showcasing entrepreneurs, entertainers, and celebrities who have made a name for themselves before reaching the age of 30.

He also released three new songs, titled "Honey", "Somethin Tells Me" and "Get Mine", with the latter featuring rapper Young Thug.

[36] In the same month, DJ Khaled released "Wild Thoughts" featuring Tiller and singer Rihanna, which is the fourth single from his tenth studio album, Grateful.

[46] On October 21, 2021 Jack Harlow released "Luv is Dro" as a single and music video, which featured Tiller and Static Major.

[47] On October 31, 2021, Tiller released a mixtape, Killer Instinct 2: The Nightmare Before, on a private link that he texted to his fans using the community number he had made earlier in 2020.

The mixtape featured a variety of freestyles over current beats at the time, including Normani's "Wild Side", Brent Faiyaz's "Gravity" and Busta Rhymes' "New York Shit".

Tiller said the project was inspired by Ariana Grande and Justin Bieber, the latter of whom features in a song titled "Lonely Christmas".

On October 18, 2022, Tiller released a music video for the single which featured an appearance from The Ying Yang Twins.

[52][53] Despite positive reviews from critics,[54] it performed moderately in comparison to its predecessors, debuting at number twelve on the Billboard 200, with first-week album-equivalent units of 39,000.

Just a little over two weeks later on February 12, 2025, Tiller teased an all RNB mixtape on his personal Instagram account titled, "Solace".

[59][60] In addition, Tiller listed Jazmine Sullivan, Usher, Rihanna, Beyoncé, Jay-Z, The Notorious B.I.G., and Mary J. Blige as impactful to his musical socialization.

[63][58] During the recording of True to Self, Tiller struggled with depression, which according to him can be heard in the music and was the reason of the album's disappointing commercial performance.

[66] According to Justin Charity of The Ringer, "Tiller's lack of a full-time public persona is one of the young R&B singer's most endearing qualities".