During his Billboard cover shoot, Diplo sat down to look back at some memorable moments from throughout his career, including his very first time attending the Grammy Awards, working with his hero Madonna, performing with Justin Bieber, and his most recent Grammy win.

The episode of Throw It Back begins as Diplo is shown a red carpet picture of himself and Switch at the 2009 Grammy Awards, when he was nominated for record of the year for producing and co-writing M.I.A.’s “Paper Planes.”

“I had a flask,” he tells Billboard. “I didn't think I was ever gonna be invited back to the red carpet, so we were acting like complete assholes at the Grammys. But it's a good photo!”

Diplo is next shown the 2013 music video for “Biggie Bounce,” which he notes was filmed in Atlanta while he was there for a layover. Armed with $5,000, they went to a union hall and asked if they could film a video there. “I brought a little DJ setup and I played and all the elderly people were excited,” he remembers. “We danced on the tables…This is actually what my life was like, this kind of party.”

Another music video Diplo watches is Major Lazer’s 2015 “Lean On,” which they filmed in India. He recalls that they had two days off between shows, and MØ flew out to Bombay where they filmed in the suburbs and learned the choreography in 20 minutes.

In the Throw It Back episode, Diplo also chats about his friendship with Madonna, after being shown an image of them together in 2015.

“I love Madonna so much,” he shares. “I used to be a huge fan of Madonna…Basically she was my first idea of a pop star. So when I got to meet her and hang with her and work with her it was like a dream come true. And I've done I think four songs, six songs with her now. And we're friends, we speak a lot so, she's one of my heroes.”

Diplo also sheds some light on his 2016 Grammys performance with Justin Bieber. “I pretended to play the keyboards here for ‘Where Are Ü Now,’ which won two Grammys, Jack Ü song,” he explains. “I actually did play the drums live, but the keyboards was kinda…it wasn't really that real. And then the drummer was the drummer from Incubus. And then Justin Bieber forgot some of the lyrics.”

You can check out the full video above to watch Diplo react to more career moments, such as 2017’s “Get It Right,” 2018’s “Welcome to the Party” with Lil Pump, French Montana, and Zhavia Ward, “Thunderclouds” with Labrinth and Sia, and when he earned a Grammy in 2019 for Silk City and Dua Lipa’s “Electricity.”