Artists who won Video of the Year and Video Vanguard awards at the MTV VMAs

Vanguard Award: Gabriel was 37 when he won the Vanguard in 1987. He won it the same year he won Video of the Year, a double feat only one other artist has ever achieved. (Read more.)

Video of the year: Gabriel won for the incredibly imaginative “Sledgehammer,” which still holds the record for most wins for a single video (nine). Six years later, he was nominated again for “Digging in the Dirt.”

Vanguard Award: In 1995, REM became the third American band to receive this honor, following Bon Jovi (1991) and Guns N' Roses (1992).

Video of the year: The band won on their first nomination in 1991 for the stunning clip of their big hit “Losing My Religion.” They received two consecutive nominations in 1993 and 1994 for “Man on the Moon” and “Everybody Hurts.”

Vanguard Award: Spears was 29 when she received the award in 2011. Her award was presented by Lady Gaga, who will join this list once she and MTV can agree on the correct year for her Vanguard presentation. (Gaga received MTV's “Tricon” award in 2020, the only time the show has given out the prize to date.) She won video of the year in 2010 for “Bad Romance.”

Video of the year: Spears won in 2008 for “Piece of Me.” Four years earlier, she was nominated for “Toxic” and again in 2009 for “Womanizer.”

Vanguard Award: Timberlake became the second (and youngest) artist to win both awards on the same night, accomplishing the feat in 2013 when he was 32 years old.

Video of the year: He won for “Mirrors.” It was his fifth (and most recent) nomination in the category, following his *NSYNC-era hits “Bye Bye Bye” (2000) and “Gone” (2002) and his solo hits “Cry Me a River” (2003) and “What Goes Around… Comes Around” (2007).

Vanguard Award: The award was presented to the then 32-year-old Beyoncé in 2014. She was the second black woman to receive this honor after Janet Jackson in 1990. Beyoncé was presented with the award by her husband Jay-Z and her then two-year-old daughter Blue Ivy Carter.

Video of the year: Beyoncé has won twice, in 2009 for “Single Ladies (Put a Ring on It)” – “one of the best videos of all time,” as one authority put it – and again in 2016 for “Formation.” She has also been nominated for “Irreplaceable” (2007); “Telephone” (2010), a collaboration with Lady Gaga; “Drunk in Love” (2014), a collaboration with Jay-Z; “7/11” (2015); and “Apeshit” (2018), another collaboration with Jay-Z (as The Carters).

Vanguard Award: The award was presented to Rihanna, then 28, in 2016. Her frequent collaborator Drake presented the prize.

Video of the year: Rih has also won twice, for “Umbrella” (featuring Jay-Z) in 2007 and “We Found Love,” a collaboration with Calvin Harris, in 2012. She was also nominated for “Take Care” (2012), a collaboration with Drake, and “Wild Thoughts” (2017), a collaboration with DJ Khaled and Bryson Tiller.