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5. Woody Allen’s Surprise Appearance

As the nation reeled from the September 11, 2001 attacks, it took a while to be truly comfortable with laughing and having fun again. Awards shows, always banal, seemed particularly trivial in the aftermath of those tragedies. But when one of New York’s dearest decided to set aside his distaste for awards season and the Oscars and stun everyone by appearing almost disheveled (i.e. in true form) at the Academy Awards, to pay tribute to the city he so loves, it was an iconic and genuinely moving moment as any there have been in the history of the Oscars. Woody Allen, always controversial, set his own views and politics aside, as most did, to unite behind something more important than the Oscars themselves. What could be more iconic than that?

4. Whoopi Goldberg’s African Queen

I loved most of Billy Crystal’s moments (perhaps I’m alone in that) and really enjoyed Ellen’s first turn as host, particularly when she vacuumed from under celebrities and took pictures with Martin Scorsese and Clint Eastwood. But for whatever reason, Whoopi Goldberg’s entrance into the 1999 telecast sticks with me. Her face, smothered in white make-up, is deadpan but clearly concealing a smile. And, in a classic cross-reference moment she declares herself to be everyone’s “African Queen.” She then adds that some think of her as the Virgin Queen (an obvious and clever reference given that two movies that had connection to Queen Elizabeth were up for Best Picture that year). I think it was Whoopi’s most shining moment as host, and perhaps one of the most iconic moments by any host not named Bob Hope.

3. The Kiss

When Halle Barry’s lips gave way to the words “Adrien Brody” during the 2003 telecast, all of us were truly surprised. Perhaps one of the last true shockers in the last 10 or so years of Oscars (not counting close or toss-up races), Brody defeated favorites (but past winners) Jack Nicholson and Daniel Day-Lewis for his portrayal of the title character in the Holocaust movie The Pianist. Brody’s victory was part of a larger surge of support for the movie - resulting also in a surprise Best Director win for Roman Polanski over the director of the eventual Best Picture winner - that probably means that The Pianist was inches away from overtaking the prohibitive favorite, Chicago. So, already, Brody’s victory is noteworthy in its own right for being an all-out, true shocker.

But what happened next is what landed this moment on this list. Brody, in genuine disbelief, approached the stage. He climbed it, and then, as if on the same drugs that had propelled Jack Palance into a new youthful existence, grabbed Halle Barry, bent her over, and French-kissed her on the lips. Yup, in front of a billion people or so (and his Oscar was in hand, behind her). Halle’s horrified face is as part of the iconic nature of this moment as Brody’s act itself, but whatever you may think of this bizarre invasion of her privacy, this moment is surely etched in the annals of Oscar history as iconic - and the jury is still out on whether it was a good or bad moment. It probably always will be.

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