A$AP Rocky may be dropping braggadocious bars on his latest album about scooping up Rihanna, but even he remembers when he wasn’t quite cool enough to hang with the pop star.
The 37-year-old rapper appeared on “The Tonight Show Starring Jimmy Fallon” to promote his new album “Don’t Be Dumb,” when the conversation turned to how he first met the 37-year-old singer and beauty mogul.
Fallon brought up the couple’s growing family, including sons RZA, 3, and Riot, 2, and their newest baby, Rocki, who Rocky said is making him feel like “a new man,” which prompted the host to ask how the famous duo first crossed paths.
Rocky recalled meeting the “Pon de Replay” singer outside a New York hotspot long before he became a household name, but when she was already on the rise.
“I wasn’t famous at the time. She was obviously Rihanna. And I couldn’t get in,” he admitted.
“The bouncers didn’t want to let me in,” he continued. “I was with my friend, the late, great Virgil Abloh and Matthew Williams, and we kinda was getting into it with the bouncers and she came out and we locked eyes right away. I was just like, in a daze.”
When Fallon asked whether Rihanna stepped in to help him get inside, Rocky said no with a laugh.
“I was a little embarrassed that she caught me bickering with the guard and stuff like that,” he added.

He has certainly come a long way from the Harlem native arguing with club bouncers—so far, in fact, that he’s now in a position to give back to the same streets that raised him. During the interview, Fallon also revealed a good deed Rocky recently did under the radar: paying rent for all of the tenants in his grandmother’s building.
“I grew up in, you know, the homeless shelter system,” he explained. “And for me, you know, when I look online and stuff, and I see, like, TikToks of people doing things like donating to, you know, homeless people, it’s usually with a camera there. And for me, that’s a little pretentious, or, like, you know, it’s a little embarrassing for the recipient. So, I wanted to do something that felt like, you know, giving back, but without, like, trying to be too much flashy about it.”
Rocky said he was motivated by an act of kindness he experienced in his youth. He remembered being at the Voices of America shelter in the 2000s, around the time the first “Harry Potter” film came out. He couldn’t afford to go, but a volunteer offered to take a group of 10 kids to see it. Afterward, Rocky recalled asking her if she was rich.
Her answer stayed with him. She wasn’t wealthy at all, he said, just a struggling substitute teacher doing it out of pure generosity.
“I was just like, people do that?” he said.
The interview comes as Rocky and Rihanna have been spotted galavanting around New York City amid his album drop on Jan. 16, a listening party in the Big Apple, and an appearance on “Saturday Night Live,” making headlines for popping up at local eateries, of course, in style. In one buzzy moment in particular, Rihanna had a brief run-in with a bodyguard who failed to hold the door open for her as she exited the Four Seasons Hotel.
She took it in stride, though, laughing as she quipped, “Such a gentleman you are,” before stepping in her waiting car.

