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Vanguard Award: Madonna was, appropriately, the first woman to be awarded the Vanguard. She was 28 when she received the award in 1986.

Video of the Year: The Queen of Pop finally won in 1998 for “Ray of Light.” It was her third nod in the category. She had notched back-to-back nominations in 1989 and 1990 for her classic videos to “Like a Prayer” and “Vogue.” She was nominated for a fourth time for “Hung Up” in 2006.

Vanguard Award: Gabriel was 37 when he was awarded the Vanguard in 1987. He got it the same year he won video of the year, a double feat that has been achieved by only one other artist. (Read on.)

Video of the Year: Gabriel won for the wildly imaginative “Sledgehammer,” which still holds the record for the most wins by a single video (nine).  He was nominated again six years later for “Digging in the Dirt.”

Vanguard Award: In 1995, R.E.M. became the third American band to receive the honor. They followed Bon Jovi (1991) and Guns N’ Roses (1992).

Video of the Year: The band won in 1991, on their first nomination, for the stunning clip for their great hit “Losing My Religion.” They went on to receive back-to-back nods in 1993-94 for “Man on the Moon” and “Everybody Hurts.”

Vanguard Award: Spears was 29 when she received the honor in 2011. Her award was presented by Lady Gaga, who will join this list just as soon as she and MTV are able to settle on the right year for her to get the Vanguard. (Gaga was the recipient of MTV’s “Tricon” award in 2020, the show’s lone time to date handing out the award.) She won video of the year in 2010 for “Bad Romance.”

Video of the Year: Spears won in 2008 for “Piece of Me.” She had been nominated four years earlier for “Toxic” and would be nominated again in 2009 for “Womanizer.”

Vanguard Award: Timberlake was the second (and most recent) artist to receive both of these awards the same night. He achieved the feat in 2013, when he was 32.

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 smashes “Cry Me a River” (2003) and “What Goes Around… Comes Around” (2007).

Vanguard Award: Beyoncé, then 32, received the honor in 2014. She was the second Black woman to receive the honor, following Janet Jackson in 1990. Bey’s award was presented by her husband Jay-Z and their 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 greatest videos of all time,” in the memorable words of one authority – and again in 2016 for “Formation.” In addition, she was nominated for “Irreplaceable” (2007), “Telephone” (2010), a collab with Lady Gaga; “Drunk in Love” (2014), a collab with Jay-Z; “7/11 (2015) and “Apeshit” (2018), another collab with Jay-Z (as The Carters).

Vanguard Award: Rihanna, then 28, received the honor in 2016. Her frequent collaborator Drake presented the award.

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

Vanguard Award: P!nk was 37 when she received the award in 2017.

Video of the Year: She had won in 2001 for the all-star remake of LaBelle’s “Lady Marmalade” which also starred Christina Aguilera, Lil’ Kim and Mýa and which featured Missy Elliott. Surprisingly, that’s her only video of the year nod.

Vanguard Award: Elliott was 48 when she received the honor in 2019. She was the first female rapper to receive the honor, which was presented by another female rapper, Cardi B.

Video of the Year: She has won twice, once as a featured artist and once as the lead. She won in 2001 as a featured artist on the all-star remake of LaBelle’s “Lady Marmalade” by Christina Aguilera, Lil’ Kim, Mya and P!nk. She won again two years later for her own “Work It.” She was the second artist to win twice in the category, following Eminem. She was also nominated for “Get Ur Freak On” (2001).

Vanguard Award: Perry, 39, is slated to receive the award on this year’s show on Sept. 11.

Video of the Year: She won video of the year in 2011 for “Firework.” She was nominated again the following year for “Wide Awake.”