In 2015 they released the single FourFiveSeconds - a collaboration with Kayne West.
And, Rihanna, 31, reunited with Sir Paul McCartney, 77, on Friday as they bumped into each other while in first class on the same flight from JFK airport in New York to London's Heathrow.
The duo were in high spirits as they landed in the capital, after the Rude Boy hitmaker had taken to her Instagram stories to document their encounter, which she caption #RihUnion.
RihUnion: Rihanna, 31, reunited Sir Paul McCartney, 77, on Friday as they bumped into each other while in first class on the same flight from JFK airport in New York to London's Heathrow
Rihanna was wrapped up warm as she departed the flight, clad in a grey tracksuit with a white cardigan and a khaki coloured teddy coat.
The Fenty entrepreneur strolled through the airport in white trainers and finished off her sporty look with a New York Yankees baseball cap atop her head.
The singer accessorised with a smattering of metallic necklaces and large hoop earrings, while shielding her eyes with a glamorous pair of black shades.
Rihanna appeared to be make-up free, and tied her raven locks back into a ponytail, adding a splash of colour with a pillar box red manicure.
Stylish: Rihanna was wrapped up warm as she departed the flight, clad in a grey tracksuit with a white cardigan and a khaki coloured teddy coat
First class company: The Rude Boy hitmaker had taken to her Instagram stories to document their encounter, which she caption #RihUnion
Jokers: 'Who is this filming me?' joked Paul, with Rihanna laughing as she teased him, saying: 'Who is the peasant filming this legend?'
Former colleagues: In 2015, Rihanna and Paul McCartney released the single FourFiveSeconds - a collaboration with Kayne West
Meanwhile, Paul opted for an all-black ensemble, with a long sleeved T-shirt and plain trousers.
But the music icon layered up with a smart textured coat featuring a subtle burgundy check as they touched down in London.
Filming Paul standing in the aisle, Rihanna told him: 'I'm about to put you on blast Mr McCartney.'
Different looks: The Fenty entrepreneur strolled through the airport in white trainers, while Paul looked smart in his all-black attire
Looking good: Rihanna finished off her sporty look with a New York Yankees baseball cap atop her head and accessorised with a smattering of metallic necklaces and large hoop earrings
Baby it's cold outside: The music icon layered up with a smart textured coat featuring a subtle burgundy check as they touched down in London
Gorgeous: She tied her raven locks back into a ponytail, and added a splash of colour with a pillar box red manicure
'What's going on here?' asked the former Beatles star as Rihanna quizzed: 'How are you on my plane?'
'Who is this filming me?' joked Paul, with Rihanna laughing as she teased him, saying: 'Who is the peasant filming this legend?'
'Yeh that's what I mean,' quipped Paul as Rihanna continued giggling.
Looking good: After his fun on the plane, Paul wrapped up before venturing out into the cold