Trippie Redd merges cloud rap, emo rap, and trap with influences drawn from T-Pain, Gucci Mane, and Lil Wayne, while channeling punk and metal energy modeled on Slipknot and Marilyn Manson. Online tracks he dropped in 2015 quickly generated mainstream traction thanks to his flexible genre approach, and multiple projects soon entered the higher tiers of the Billboard rankings, among them the 2019 mixtape A Love Letter to You 4 and the 2023 studio album MANSION MUSIK. Before the year closed he issued the EP Saint Michael, then joined mgk in 2024 for the collaborative EP genre: sadboy.
Michael Lamar White IV was born in 1999 and grew up in Canton, Ohio, where he launched his rap career while still in his teens. The car-accident death of his aspiring-rapper brother when Trippie was ten spurred him to pursue the ambitions his sibling could no longer chase. Early mixtapes and videos circulated widely enough to secure a contract with the Universal-distributed label Strainge Entertainment, although he later aligned with the independent imprint 10K Projects. After issuing 2016’s Beast Mode and Awakening My InnerBeast, he unveiled his most substantial effort to date with 2017’s A Love Letter to You, which reached the Top 100 on the Billboard 200. A Love Letter to You 2 arrived the same year and landed inside the Top 40 of that chart; that month he also paired with Lil Wop on the EP Angels & Demons. By year’s end the Travis Scott-assisted “Dark Knight Dummo” had become his first Hot 100 entry.
Several 2018 singles paved the way for his debut studio album, Life’s a Trip. The project spotlighted his singular voice across both rapped and sung passages and marked the first of consecutive Top Ten Billboard 200 appearances. A Love Letter to You 3 followed months afterward, extending his catalog of anguished, introspective material delivered in sung and rapped forms. By then Trippie had left Ohio, spending a short time in Atlanta before settling in Los Angeles. His second studio album, !, arrived in 2019 and debuted at number one on the Billboard 200; its title referenced the late XXXTentacion’s album ? and sustained Trippie’s emo-rap themes.
The commercial mixtape A Love Letter to You 4 surfaced late in 2019, opening at the summit of the Billboard charts and surpassing 100 million streams in its opening week. An expanded edition issued the following year added tracks featuring Lil Tecca and Chance the Rapper, setting the stage for the third studio album Pegasus, released in October 2020. That set included appearances by Young Thug, Future, Busta Rhymes, and others, entering the Billboard charts at number two. Early 2021 brought the deluxe edition Neon Shark vs. Pegasus, after which Trippie previewed his fourth album with the Playboi Carti-assisted single “Miss the Rage.” Trip at Knight followed in August 2021, featuring Drake, Ski Mask the Slump God, SoFaygo, and posthumous contributions from Juice WRLD on “Matt Hardy 999” and XXXTentacion on “Danny Phantom.”
Trippie opened 2022 with “Big 14” alongside Offset and Moneybagg Yo, then issued the two-song release First Draft and the Don Toliver collaboration “Ain’t Safe.” Early 2023 saw the arrival of “Way Back,” a link-up with Skrillex and PinkPantheress. The 25-track album MANSION MUSIK appeared soon after, boasting guests such as Chief Keef, G Herbo, and Lil B, and peaked at number three on the Billboard 200. A Love Letter to You 5 arrived several months later. In November 2023 the EP Saint Michael capped the year, climbing as high as number 161 on the Billboard charts. March 2024 brought the ten-track collaborative EP genre: sadboy with mgk, a collection of depressive emo rap that reached number 30 on the Billboard 200.
