Movies Gallery Drake and Rihanna Through the Years By Madeline Boardman Madeline Boardman Madeline Boardman is a former digital features director at Entertainment Weekly. She left EW in 2017. EW's editorial guidelines Published on August 29, 2016 04:14PM EDT Trending Videos Close this video player 01 of 11 Drake and Rihanna Through the Years Kevin Winter/Getty Images; Kevin Mazur/WireImage Drake and Rihanna had a major moment at Sunday's 2016 Video Music Awards, when Drake took the stage to present Rihanna with the show's Video Vanguard Award. "She's someone I've been in love with since I was 22 years old," Drizzy said of his "Work" collaborator. "She's one of my best friends in the world." See photos of the two through the years, ahead. 02 of 11 Rihanna and Drake at Drake's Afterparty at Greenhouse in New York City on September 28, 2010 Johnny Nunez/WireImage 03 of 11 Rihanna and Drake in Rihanna's 2010 'What's My Name' Music Video 04 of 11 Drake and Rihanna Performing at the 53rd Annual Grammy Awards in Los Angeles on February 13, 2011 Kevin Winter/Getty Images 05 of 11 Rihanna and Drake Performing at the NBA All-Star Game Halftime at the Staples Center on February 20, 2011 Noah Graham/NBAE via Getty Images 06 of 11 Drake and Rihanna at an Oklahoma City Thunder and the Los Angeles Clippers game at the Staples Center in Los Angeles on April 9, 2014 Noel Vasquez/GC Images 07 of 11 Drake and Rihanna in Rihanna's 2016 'Work' Music Video 08 of 11 February 24, 2016 Samir Hussein/Redferns 09 of 11 Rihanna and Drake in Toronto Instagram.com/champagnepapi 10 of 11 Drake Presenting Rihanna With the Video Vanguard Award at the 2016 MTV Music Video Awards at Madison Square Garden in New York City on August 28, 2016 Jason Kempin/Getty Images 11 of 11 Rihanna and Drake at the 2016 MTV Video Music Awards on August 28, 2016 Kevin Mazur/WireImage