2016–2018: Career beginnings and ''Life's a Trip'' Lil Wop helped Redd get started with a professional recording studio. They began working with Kodie Shane and recorded three projects:
Awakening My Inner Beast,
Beast Mode and
Rock the World Trippie. On May 26, 2017, Redd released his debut
mixtape,
A Love Letter to You, with the lead single "
Love Scars". The mixtape peaked at number 64 on
Billboard 200 over 4 months after its release, staying on the chart for 45 weeks. Redd was the sole feature on
XXXTentacion's album
17, the song "
Fuck Love" which peaked at number 28 on the
Billboard Hot 100. In 2023, the song was certified Diamond by the
RIAA for moving over 10 million units, becoming Redd's first song to achieve this. On October 6, 2017, Redd released his second mixtape,
A Love Letter to You 2. The album debuted at number 34 on the
Billboard 200. Later that month, Redd released a collaboration EP with Lil Wop,
Angels & Demons. On December 6, 2017, Redd released the single "
Dark Knight Dummo", featuring
Travis Scott. The song peaked at 72 on the
Billboard Hot 100, making it Redd's first entry on the chart as a lead artist. On December 25, 2017, Redd released the song "TR666" on his SoundCloud account, which features
Swae Lee and was produced by
Scott Storch. The track was previewed on November 30. Redd released "18" alongside
Baauer,
Kris Wu,
Joji and
Rich Brian. In an interview with
Billboard in March 2018, Redd said his debut studio album would feature collaborations with
Lil Wayne and
Erykah Badu. In July 2018, soon after the passing of his close friend XXXTentacion, Redd announced that the album would be titled ''
Life's a Trip and be 26 tracks long; he later trimmed it to 16 tracks. Redd released the singles "Me Likey" and "How You Feel" on June 22, 2018, and "Taking a Walk" on August 6, 2018. Life's a Trip
was released August 10, 2018, and debuted at number four on the Billboard
200 album chart, with the single "Taking a Walk" debuting at number 46 on the Billboard
Hot 100 chart. Later in 2018, Redd released A Love Letter to You 3, which reached number three on the Billboard'' 200.
2019–2020: !, A Love Letter to You 4, and Pegasus On May 29, 2019, Redd released "
Under Enemy Arms", the lead single to his second studio album
!. On July 24, 2019, Redd released the second single for the album, "
Mac 10", featuring
Lil Baby and Lil Duke. The album was released on August 9, 2019, and debuted at number three on the US
Billboard 200 with 51,000 album-equivalent units. He also released a collaboration with
Juice Wrld titled "
Tell Me U Luv Me", which reached the top 40 on the
Billboard Hot 100. On May 15, 2020, Redd released the single "Excitement" with
PartyNextDoor, as the lead single for his third studio album,
Pegasus. On June 18, which was his 21st birthday, he released another single titled "Dreamer", a single for
Neon Shark, the deluxe edition of
Pegasus, which would be his "rock album". On August 18, the entire album leaked after Redd had stated that he would delay the album even further if more of his music continued to leak online. On September 11, he released the single "I Got You", featuring
Busta Rhymes, as the second single from
Pegasus. On October 7, he released the third and final single, "Sleepy Hollow", from the album. The album was released on October 30, 2020, and debuted at number two on the
Billboard 200.
2021–2022: Trip at Knight and Neon Shark vs Pegasus Redd began the year by releasing the deluxe edition of
Pegasus, a rock reissue titled
Neon Shark vs Pegasus. He later announced his fourth studio album
Trip at Knight, which was expected to release later in the year. In the lead-up to the album's release, Redd released two high-profile collaborations. The first, "
Miss the Rage" with
Playboi Carti, debuted at number 11 on the
Billboard Hot 100, becoming the highest-charting single of Redd's career. The second lead single was "
Holy Smokes" featuring
Lil Uzi Vert, which peaked at number 50 on the Hot 100. On August 11, Redd announced the album's tracklist, as well as a tour set to begin on August 25.
Trip at Knight released on August 20, 2021, with the song "Betrayal" featuring
Drake added to the album's track listing a day late on August 21. On September 9, 2021, someone had opened fire on Redd's tour bus, striking the driver.
2023–present: Mansion Musik, A Love Letter to You 5, Genre: Sadboy, and NDA Redd released his fifth studio album,
Mansion Musik on January 20, 2023. The album peaked at number 3 on the
Billboard 200 and saw mixed reviews. Redd's fifth commercial mixtape
A Love Letter to You 5 released on August 11, 2023. In late 2023, Redd released his 7-track EP,
Saint Michael. Subsequently,
Saint Michael V2, an expanded edition of the project, would release in November 2023. In March 2024, Redd announced a collaborative extended play with American musician
MGK, titled
Genre: Sadboy. It was released on March 29, 2024, to negative reviews. In early October 2024,
KSI and Redd released the single "
Thick of It". It received very negative criticism. Redd's sixth album,
NDA, is in development; he released the singles "Woke Up" and "The Face" in July 2025. It is set to feature a guest appearance from
Kanye West. ==Artistry==