His debut mixtape A Love Letter to You (2017) and its lead single "Love Scars" propelled him to popularity. Trippie Redd's singles "Dark Knight Dummo", featuring Travis Scott, and "Topanga", both reached the Billboard Hot 100. His debut studio album Life's a Trip (2018)[6] and second album ! (2019)[7] both reached the top five of the Billboard 200, while his fourth mixtape A Love Letter to You 4 (2019) topped the chart.[8]