Illustration by Jillian Tamaki

Madonna, who rose from her Michigan roots to become the Queen of Pop, turns 50 this Saturday. Madge’s star has shone so bright over her 25+ years career that it’s difficult to select just a handful of career highlights, let alone highlights that haven’t been played to death on VH1. Here, in honour of Madge’s 50th, is a rundown of 10 of Madonna’s most interesting, under-appreciated or downright bizarre moments:

1. Though she’d already hit the Billboard charts with catchy pop singles Borderline and Lucky Star, it was this smoldering performance at the 1984 MTV video awards that first hinted at Madonna’s raw star power and plans for world domination.
2. Yes, she’s taken a critical drubbing for most of her film output (and has at least 15 Razzie Awards to prove it), but Madonna turned in a spunky, highly watchable performance -- as a thinly disguised version of herself -- in the early-80’s gem Desperately Seeking Susan.
3. She’s been linked to a number of famous men in her lifetime (Sean Penn! Warren Beatty! Dennis Rodman!), but it’s Madonna’s friendships with women (Rosie! Gwyneth! Britney!) that have generated the most buzz and gossip-column fervour. In particular, her ambiguous relationship with Sandra Bernhard raised eyebrows and helped to put a public face on bisexuality.
4. Like any pop icon worth her salt, Madonna has never shied away from controversy. In her noble efforts to break boundaries, she occasionally goes too far (Sex, anyone?), as in this notorious, bleep-laden appearance on David Letterman.
5. She rose to fame at the advent of the MTV age, and throughout her career, Madge has been unrivalled in her ability to exploit the video medium to its very fullest. Though she might be best known for censor-baiting clips à la Like a Prayer, she also deserves props for this trio of late-’80s videos, directed by then up-and-coming film director David Fincher: melancholy mini-movie Oh Father, Bad Girl (in which Christopher Walken watches over her masochistic character), and the uber-hot Metropolis send-up Express Yourself.
6. Justify My Love. Easily the best video of Madonna’s career, this arty montage of grainy black-and-white sexual fantasies set to slow-burn music was actually one of the first-ever clips to be banned by MTV. Not coincidentally, when the uncensored, extended version of Justify My Love was sold at record stores as a video, it went on to become one of the highest-selling video singles of all time.
7. Never one to smile and keep her mouth shut, Madonna had the nerve to voice what many had been thinking but were too polite to say when she made a gagging motion and dissed bland star Kevin Costner in the documentary Madonna: Truth or Dare.
8. Despite the grumblings of casting directors, other actresses and a whole bunch of angry Argentina residents, Madonna won the lead role of Eva Peron in the film version of Evita, and her big Don’t Cry for Me Argentina moment ranks among her best, most understated moments on film. Proving her detractors wrong, Madonna walked off with a Golden Globe Award for her work in the movie.
9. Madonna’s career has been filled with so much blonde ambition, one could be forgiven for overlooking her more altruistic side. But she should be praised for her ongoing work for a variety of charities, and in particular for her ongoing work as an outspoken AIDS activist.
10. Just when it seemed impossible for Madonna to invent herself one more time, she released Hung Up, a video where she can be seen krumping and shaking her yoga- toned booty, proving once and for all that, even at almost-50, she’s still hipper and, well, hotter than most pop stars half her age.

Happy 50th, Madge!

-- Lee Ferguson