Rihanna followed in the footsteps of legends before her including Michael Jackson, Madonna, Beyoncé, Kanye West, and Janet Jackson as the latest recipient of the Michael Jackson Video Vanguard Award.

Eleven years after making her debut with “Pon de Replay,” the girl from Barbados reflected on her illustrious career, including 14 No. 1 singles and eight albums, with four performances throughout the course of Sunday’s show.

After her fourth medley of the night, Drake emerged on stage at Madison Square Garden to bestow praise upon his “Work” collaborator and girlfriend.

As RiRi stood behind him, a tuxedo-clad Drizzy reflected on their first encounter on set of the “Pon De Replay” video in Toronto. “The first time I met Robyn Fenty was 2005,” he said.

He continued, “Some artists need to play a character to achieve success. Some need to downplay their own natural instincts to blend in. She succeeds by doing something that no one in this music industry does, which is being herself.”

He also addressed the romance rumors. “She’s someone I’ve been in love with since I was 22 years old,” gushed Drizzy, while calling her one of his “best friends in the world.”

“All my adult life I’ve looked up to her even though she’s younger than me,” he said. “She’s a living, breathing legend in our industry.”

 

Rihanna followed in the footsteps of legends before her including Michael Jackson, Madonna, Beyoncé, Kanye West, and Janet Jackson as the latest recipient of the Michael Jackson Video Vanguard Award.

Eleven years after making her debut with “Pon de Replay,” the girl from Barbados reflected on her illustrious career, including 14 No. 1 singles and eight albums, with four performances throughout the course of Sunday’s show.

After her fourth medley of the night, Drake emerged on stage at Madison Square Garden to bestow praise upon his “Work” collaborator and girlfriend.

As RiRi stood behind him, a tuxedo-clad Drizzy reflected on their first encounter on set of the “Pon De Replay” video in Toronto. “The first time I met Robyn Fenty was 2005,” he said.

He continued, “Some artists need to play a character to achieve success. Some need to downplay their own natural instincts to blend in. She succeeds by doing something that no one in this music industry does, which is being herself.”

He also addressed the romance rumors. “She’s someone I’ve been in love with since I was 22 years old,” gushed Drizzy, while calling her one of his “best friends in the world.”

“All my adult life I’ve looked up to her even though she’s younger than me,” he said. “She’s a living, breathing legend in our industry.”

The couple showed some rare PDA as Drake kissed her on the neck and they embraced for a moment.

A humbled RiRi acknowledged her friends, fans, and native country of Barbados in her acceptance speech. “They’re gonna be so proud. This is the first Vanguard to land anywhere close to my country,” she said as friends including Naomi Campbell looked on.

“It started as my dream, but now my success is not my own. It’s my family’s. It’s my fans. It’s my country’s. It’s the Caribbean as a whole. It’s women. It’s black women,” she added.

“There’s so much growth that has happened over the last 11-and-a-half years, and I can’t believe I’m receiving a Michael Jackson Video Vanguard Award at 28 years old,” said Ri before holding hands with Drake and walking offstage.