Credit: Lil Durk

Lil Durk has recorded a lot of music in his career across his eight studio albums, 12 mixtapes and countless guest appearances, but there’s one song that, in his opinion, clearly stands out above the rest. Just as the pandemic was putting the world on pause, the Chicago rapper managed to secure a collaboration with Drake thanks to a random direct message on Instagram.

The pair teamed up on ‘Laugh Now Cry Later’ in 2020, which Lil Durk has cited as his favourite song he’s ever made. During an interview, he stated the track took his career to another level, and, fascinatingly enough, took just five minutes for him to record. “It’s gotta be the Drake song, ’cause that was the one that took it to another level,” he said. “When he DM’d me like, ‘Send me your number. I got one for you.’ He FaceTimed me, he played the song. He was like, ‘I ain’t gon’ lie, I need it tonight.’

“It was the beginning of the pandemic so the studio was closing early. He was like, ‘I need it back right now.’ I did this quick ass shit. I left the studio, he called me back like, ‘Man, this shit hard. What the fuck, you did this shit in five minutes? Put eight more bars on it, I’ma drop it ASAP.’ I was telling him, ‘Shit, the studio closed ’cause of the pandemic.’ That was the best eight bars I ever did in my life.”

Not only is ‘Laugh Now Cry Later’ a personal favourite for Lil Durk, but it’s also one of his most successful songs. The single peaked at number two on the Billboard 200 and was nominated for Best Rap Song and Best Melodic Rap Performance at the Grammys.

Lil Durk has credited his Drake collaboration as the reason for his show booking price shooting up from $40,000 to $100,000. “My show price was $40,000, and we were debating for a long time, ‘Should we go to $60,000?’ We were in the studio having this conversation,” he told Million Dollaz Worth of Game. “This motherfucker Drake comes through and DMs me asking for my number. He sent the song through. I called everybody and told them they’re about to be rich.”

He continued, “Drake got that touch, for real. I called everybody. I told my momma, ‘It’s over with. I’m finna do this muthafucka, we finna fuck him up… and we finna go.’ The song was during the pandemic. My show price was $40,000… we went straight to $100,000. Shout out Drake, though, he definitely helped a motherfucker out.”

During the same conversation, Lil Durk claimed he was bigger than Drake in the “trenches” but still gave respect to the Toronto superstar. “Shit, to us, in this motherfucker, we bigger than [Drake], you know what I’m saying?” he said. “We touch people; Drake at a rate where he can stay in the fucking house if he want to. But nah, shout out to him. He touch the youth. That’s one thing about him. He touched us and got us hotter than what the fuck we was.

“But a lot of people can’t say that, a lot of these motherfuckers don’t even know him; a lot of people he talk to don’t know me. I’m in this motherfucker, in the middle of the trenches with a million dollars doing a fucking interview, that’s why.”

Lil Durk went on to collaborate with Drake once again in 2021 on ‘In the Bible’, which appeared on Drizzy’s Certified Lover Boy album.