Bryson Tiller

Tiller in 2016.

In October 2014, Tiller uploaded his debut single "Don't" to his SoundCloud account, which started receiving some internet attention from music industry insiders.[9] It was officially released on iTunes for digital download in May 2015, becoming the lead single of his debut studio album.[10] "Don't" peaked at number 13 on the Billboard Hot 100 chart.[11] It has been remixed by artists like K Camp, Mila J, Sevyn Streeter, DRAM and WSTRN.[12][13] Early co-signs from record producer Timbaland and rapper Drake led to major-label attention for Tiller, with him eventually choosing to sign a creative partnership with RCA Records, which was announced on August 25, 2015.[14] Tiller was offered a chance to sign with Drake's OVO Sound record label, but declined the offer.[15] In September 2015, Rolling Stone included Tiller in their list of "10 New Artists You Need to Know".[16]

On October 2, 2015, Tiller released his debut studio album, Trapsoul, which debuted at number 11 on the US Billboard 200 and later reached number eight.[17][18][19] The album's second single, "Exchange", peaked at number 26 on the Billboard Hot 100 and earned him a Grammy nomination for Best R&B Song.[11][20] "Sorry Not Sorry", which was released as the third single from Trapsoul, peaked at number 67 on the Billboard Hot 100.[11] The album was included on a number of 2015 year-end lists, such as Complex's The Best Albums of 2015, The Root's 10 Favorite Albums of 2015, and PopSugar's The 24 Best Albums of 2015.[21][22][23] In 2015, he also co-wrote the track "Proof" for singer Chris Brown's seventh studio album Royalty.[24]

Tiller performing during the Stavernfestivalen in July 2016.

In January 2016, Tiller started the Trapsoul Tour for the promotion of the album, with opening act THEY..[24] On March 12, 2016, Louisville Mayor Greg Fischer gave Tiller the key to the city and named March 12 as "Bryson Tiller Day".[25] In May 2016, Tiller made his US television debut, performing "Exchange" on the Late Night with Seth Meyers show.[26] On June 26, 2016, he performed at the BET Awards, where he also received the awards for Best New Artist and Best Male R&B/Pop Artist.[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.[28] In September 2016, Tiller also appeared on the track "First Take" by rapper Travis Scott, from Scott's second studio album, Birds in the Trap Sing McKnight.[29]

In January 2017, he was included on 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.[30] In the same month Tiller announced that his second album will be titled True to Self.[31] On April 12, 2017, Tiller tweeted that work on his second album, True to Self, had been wrapped up.[32] On May 11, 2017, Tiller revealed the album artwork and that True to Self would be released on June 23, 2017. He also released three new songs, titled "Honey", "Somethin Tells Me" and "Get Mine", with the latter featuring rapper Young Thug.[33] On May 26, he released True to Self, a month earlier than the intended release.[34] The album debuted at number one on the Billboard 200, earning 107,000 album-equivalent units, of which 47,000 were pure album sales.[35] It became Tiller's first number one album in the country.[35]

In June 2017, Tiller partnered with Nike, Inc. to provide a new Wyandotte Park for children and teens.[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.[37] The single has peaked at number two on the Billboard Hot 100,[38] as well as reaching number one on the UK Singles Chart. In August 2017, Tiller released a collaborative single with singer Jazmine Sullivan titled "Insecure", which is the title track for the HBO series Insecure.[39] In January 2018, he performed "Wild Thoughts" with Rihanna and DJ Khaled at the 60th Annual Grammy Awards.[40]

Throughout 2019 and 2020, Tiller featured on a number of songs by other artists. In 2019, Tiller said he was waiting for sample clearances in order to release his album, titled Serenity.[1][41] In April 2020, he released the song "Slept on You" via SoundCloud.[1] On September 3, 2020, Tiller released "Inhale" and stated on his social media pages that he would release a new album in fall 2020. The second single "Always Forever", was released on September 23, with a deluxe edition of Trapsoul released on September 25,[42] in celebration of his third album, Anniversary,[43] which was released on October 2, 2020. It marks the five year anniversary of his debut album and includes a guest feature from Drake.[44]

Omarion (left) and The-Dream (right) were two of Tiller's biggest inspirations while growing up.

Tiller has cited singer Omarion as his mega influence, "[My uncle] put me on Omarion's first album, and that was the first album that made me want to start singing. I started listening to him daily and singing what I heard."[45] Singer The-Dream has inspired him becoming a lyricist, "I started listening to The-Dream a lot. That's when I really got into writing songs. I like the way he put lyrics and makes his songs. So I was like, all right, and I just started writing. That's when I started wanting to be a songwriter. I never really wanted to be an artist. I just really wanted to write songs. But of course I can't get placement unless I demo the songs."[46]

His other influences include R. Kelly, Lil Wayne, Chris Brown and Drake.[47][48] 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.[49]

Tiller has described his music as "trap and hip hop-influenced R&B, the perfect marriage between hip hop and R&B."[47] Tiller also raps saying "there are some things I can say rapping that I can't say singing".[50] Critics have compared Tiller's musical style to Drake, Jeremih, PartyNextDoor and Tory Lanez.[51][46] 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.[52] On his blend of R&B and rap, Tiller explained: "R&B is my first love and it always will be. I fell in love with hip-hop and rap music through Lil Wayne. Don't get me wrong, I love Wayne, but you know, I heard only the radio singles [..] So I said, 'Damn. Let me mix it up a little bit'".[53]