Trippie Redd Stays Humble Amid Chart-Topping Success and Heartache

Trippie Redd is bringing his Love Me More Tour to the Fillmore Miami Beach.
Trippie Redd is bringing his Love Me More Tour to the Fillmore Miami Beach. Aidan Cullen
click to enlarge Trippie Redd is bringing his Love Me More Tour to the Fillmore Miami Beach. - AIDAN CULLEN
Trippie Redd is bringing his Love Me More Tour to the Fillmore Miami Beach.
Aidan Cullen
Trippie Redd is more familiar with the emotional lows of heartache than he'd like. The Canton, Ohio, rapper has built a considerable following and endeared himself to listeners through his lovesick ballads, trademark emo wails, and all-around candidness. November 2019's A Love Letter to You 4 (ALLTY4) is the latest entry in his series of releases detailing his insights into love and heartbreak. Not one to let his emotional woes keep him down, Trippie is embarking on his Love Me More Tour, which will take him, along with supporting acts Kodie Shane and Blocboy JB, to the Fillmore Miami Beach on Leap Day. 

Trippie Redd stands out among his rap contemporaries, if not for his versatile style, then for the number of Billboard 200 hits he has accumulated during his relatively short career. All of his projects, from the 2017 mixtape A Love Letter to You to 2019’s ALLTY4, have landed on the Billboard 200. This past December 7, ALLTY4 topped the chart, awarding the 20-year-old rapper the first number one of his career.

Surprisingly humble, he claims he doesn’t like to boast about this achievement. “I try not to gloat over it too much, but it’s amazing,” Trippie tells New Times.

The mixtapes in Trippie’s adored A Love Letter to You series see the emo rapper experimenting with various genres and sonic styles under the thematic umbrella of love and relationships. “Ultimately, the goal of A Love Letter to You the mixtape brand is versatile music and love... It’s my emotions that I felt toward multiple females,” he shares.

Last year, Trippie was in a high-profile relationship with New Jersey rapper Coi Leray. They collaborated on songs such as “Everything BoZ” and "Big Dawgs.” He even brought her out onstage in Miami during his performance at the 2019 edition of Rolling Loud Music Festival. Their romance ended around the time of ALLTY4’s assembly, and many of the record's songs allude to their relationship. The first song, “Leray,” seems to include Trippie’s postbreakup musings. He mostly appears bitter, but at one vulnerable moment he admits, “I do miss who I thought you were/And sometimes I'm miserable without you.

“After ALLTY3, I was gonna chill out and not be in a relationship, but I ended up meeting this other girl and it became a different [relationship]. It ended up not working with her either, and that’s why I keep using that line, ‘I do miss who I thought you were,’ because I thought [she was] somebody different; even my family did,” Trippie divulges.

The other 20 songs on ALLTY4 smoothly transition through the five stages of grief one might feel after the dissolution of a relationship. Heartbreak and sadness abound on tracks such as “Who Needs Love” and “Love Sick.” Darker, more aggressive songs follow on the likes of “Death” and “The Grinch,” where Trippie employs bold beats and brash vocals to emphasize his anger. Toward the end, things simmer down as he explores his replenished confidence with pump-up anthems “RMP” and “M’s.”

“Songs like ‘The Grinch’ and ‘Death’ came about because... I’m angry, I’m mad. Like, damn, I had to let the screaming parts out, you know? Then I had to get my confidence back up, talk about some money, but... [ALLTY4] shows all of my emotions,” he says.

The record's emotional quality stems from more than just Trippie's romantic hardships. ALLTY4 also includes contributions from two artists whose deaths were widely mourned: XXXTentacion and Juice Wrld. “All for Me,” featuring Miami rapper Smokepurpp, concludes with an outro by the "Look at Me!" rapper, taken from an excerpt of his 2018 “My Heart and Yours” vlog. In it, XXXTentacion details how he feels hopeless about love after having been let down by partners in the past. He and Trippie were frequent collaborators and friends despite a short beef in 2018, making the Broward County artist's inclusion all the more special.

“We looked up to each other as mentors... We came up the same way: alone, by ourselves, young, but [also] different. He dealt with a lot more than I had to deal with, but I feel like the emotional attachment we both had to our music and just what we went through, that’s what made us who we are; that’s how we got as big as we got,” Trippie says of his friendship with XXXTentacion.

Juice Wrld — along with Gifford, Florida, rapper YNW Melly — appears on the popular track “6 Kiss.” Sadly, the Chicago rapper died December 8, 2019, from an accidental overdose after landing at Midway International Airport. Juice Wrld and Trippie Redd had collaborated on songs for each other’s projects frequently and were good friends, even appearing together on the popular podcast No Jumper.

ALLTY4 is an ode to many things — love, heartbreak, and, in some ways, Trippie’s late friends — and its long tracklist leaves plenty to unpack. Despite the high volume of work he has produced so far, don’t expect the Ohio rapper to slow down anytime soon. A deluxe version of ALLTY4 is set to drop this Friday, February 21, and his rock-oriented record, Neon Shark, is tentatively scheduled to be released this year.

The Love Me More Tour brings ALLTY4's 21 diverse tracks to the stage in an electrifying way; Trippie’s concerts are not known for being laid-back affairs. There's a reason his Fillmore show — like many of his other tour dates — is already sold out, but resale tickets are still up for grabs. If your Valentine's Day didn’t go as planned, this show might provide the perfect catharsis to close out February. Because, really, “Who Needs Love”?

Trippie Redd. With Kodie Shane and Blocboy JB. 8 p.m. Saturday, February 29, at the Fillmore Miami Beach, 1700 Washington Ave., Miami Beach; 305-673-7300; Resale tickets start at $137 via
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Aaliyah Pasols is a journalist who was born in Hoboken, New Jersey, but raised in South Florida. When she's not writing, she loves taking pictures, experimenting with graphic design, creating Spotify playlists, and dreaming about New York City.
Contact: Aaliyah Pasols