Drake jokes that he struggled to get signed because his 'outfit choices were horrible at the time': 'They said I looked corny'

• Drake performed the second of two shows at Harlem's historic Apollo Theater on Sunday.
• During the concert, he reflected on his first trip to New York, when many labels declined to sign him.
• "I was probably wearing some Club Monaco khakis with a button-up or something," he said. "It was terrible."

Drake opened up about his early career failures during an intimate concert in New York on Sunday.

The record-breaking rapper reflected on his rise to stardom while performing at Harlem's historic Apollo Theater. The special event, sponsored by SiriusXM, opened with a bedroom-inspired stage design that resembled his mom's basement.

A table and set of chairs were set up at the other end of the stage. This was meant to represent the ill-fated meetings with label executives during his first trip to New York, Drake said.

"I came here with my uncle, trying to get signed, you know? I think I sat in front of everybody for like, a week straight. And I got turned down by everybody for like, a week straight," he told the crowd.

"In all fairness, my outfit choices were horrible at the time," he continued. "They said I looked corny. I don't disagree. I was probably wearing some Club Monaco khakis with a button-up or something. It was terrible."

—Callie Ahlgrim (@callieahlgrim) January 23, 2023

Drake, born Aubrey Graham, began writing songs as a teenager while starring on the Canadian series "Degrassi."

He self-released his debut mixtape, "Room for Improvement," in 2006 and left TV to pursue music full-time in 2008. One year later, he was signed to Lil Wayne's label Young Money.

"The point is, I didn't get signed that trip to New York," Drake said onstage at the Apollo. "I went back home and I had to go back to my mom's basement 'cause it didn't play out like the way I thought it would. So I went back and I wrote some more songs to see if I could get signed, and eventually, somebody called."

Drake performed a variety of hits from throughout his career, including "Best I Ever Had," "Hold On We're Going Home," "One Dance," and "God's Plan."

Later in the evening, Drake thanked the audience for sticking by him for so many years and teased a tour with 21 Savage this summer.

"I've thought about maybe what it would be, like, 'Oh, it's been a good run. Maybe I should just leave while it's hot, leave while it's good,'" he said. "But the love that I still get to this day, after all these years, I'll let you know: I'll never leave you high and dry."

"As long as you listen, I'll be here for you," he added. "In your darkest moments and your happiest moments, I'll be there for you."