Tyler, the Creator has never been one to hold back, and that didn’t change during the first instalment of ‘Ask It Anyway’, a new artist-focused conversation series launched by Instagram.
Hosted by designer and ‘The Cutting Room Floor’ podcaster Recho Omondi, the chat saw Tyler dive into the highs and lows of his creative journey with his trademark wit and honesty. He kicked things off in classic Tyler fashion, brushing off any nerves: “[Omondi] was like, ‘Do you have the jitters right now, are you nervous?’ And I was like, ‘Why the fuck would I be? Nobody here has a gun.’”
Beyond the laughs, the Grammy-winning artist reflected on the turning points that shaped his career, particularly the backlash to his 2015 album Cherry Bomb. Tyler admitted he was overreaching on that record.
“My goal was to prove to myself that I am the most diverse producer at the time,” he explained. “People were just shitting on it… it made me say, oh shit – these songs aren’t good. Because of [the backlash], I was like, I need to reteach myself how to write songs. What is a chorus, hook, structure? That happening to me was one of the greatest things that could happen, because it made me dive into my skill and craft more.”
That internal reboot led to Flower Boy in 2017—a critically acclaimed pivot point in Tyler’s discography. “[That] was the first album I put on the cover to let people know: all songs written, produced and arranged by me,” he said. “You have to tell people who you are. And I remember, the conversation started changing a bit… Now people are subconsciously listening to the production in a different way now, because I let them know that.”
Throughout the session, Tyler encouraged emerging artists to embrace evolution and stay fearless in their approach. Whether reflecting on his DIY beginnings or dropping advice like “create like a child and edit like a scientist,” he made one thing clear: staying curious is key.
