6. "Shanti/Ashtangi” and “Ray of Light” (1998) View this video on YouTube Madonna -- sporting dark straight hair, a bindi, henna tattoos, and an Indian sari -- started out by performing her song "Shanti/Ashtangi," before moving onto her smash hit, "Ray of Light," accompanied by Lenny Kravitz, who played guitar. Unfortunately, her serious/faux “spiritual Earth Mother” performance of “Shanti/Ashtangi,” is a bit of a snoozer. 5. "Bye Bye Baby" (1993) View this video on YouTube Madonna -- dressed like a modern day Marlene Dietrich -- brought her Girlie Show Tour to MTV when she opened the greatest VMAs of all time with a cabaret-style performance of “Bye Bye Baby.” 4. "Express Yourself" (1989) View this video on YouTube Proving that sometimes less is more, Madonna opened up the show with an energetic rendition of her female empowerment anthem "Express Yourself" -- it also happened to be the first ever live performance of the song. 3. "Like a Virgin"/ "Hollywood" medley (2003) View this video on YouTube The most memorable opening performance in VMAs history; Britney Spears and Christina Aguilera donned wedding dresses and paid tribute to Madonna’s iconic "Like a Virgin" performance from the 1984 VMAs.Of course all anybody remembers is THE KISS. 2. "Like a Virgin" (1984) View this video on YouTube An iconic and career-defining performance that not only catapulted Madonna into superstardom, but also gave the VMAs its reputation as the show with the most shocking moments. 1. "Vogue" (1990) View this video on YouTube Madonna’s spectacular Marie Antoinette-inspired performance of “Vogue” is amazing because it didn’t rely on flashy gimmicks, special effects, or large scale sets to wow -- but rather it showcased one of her biggest strengths: her ability to dance to complex choreography. We can even forgive her for lip-synching through it.