The Mad Moment: Martin Scorsese wins Best Director...in 2007. Thus standing for all of the legends who got Oscars far, far into their careers when they should have had them earlier.
In a fit of conspicious embarrassment at the career-long slight, the Academy placated Scorsese by having three of his peers - Spielberg, Coppola and Lucas - hand over the statutette. Even then, Scorsese wasn't convinced.
How It Should Have Happened: In 1981 (instead of Robert Redford). In 1991 (instead of Kevin Costner). In 2005 (instead of Clint Eastwood). Spot a theme emerging here?