Austin Powers
Mike Myers as the swinging spy, the bald nemesis, and eventually half the cast — a three-film Bond parody whose catchphrases colonized every schoolyard in 1999. The humor ran racy for its era; the craft underneath is what stuck.
#Parody
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Galaxy Quest
The washed-up cast of a canceled space show gets abducted by aliens who watched the reruns and thought they were documentaries. "Never give up, never surrender!" The Star Trek parody so good that actual Trek fans voted it one of the best Star Trek films — and it isn't one.
Mars Attacks!
Tim Burton's $80 million love letter to a gory 1962 trading-card set: cackling bug-eyed Martians vaporizing Jack Nicholson, Pierce Brosnan, and half of Hollywood — until Slim Whitman's yodeling makes their heads explode. Five months after Independence Day played it straight, this played it very, very weird.
Scary Movie
A shameless parody of Scream, I Know What You Did Last Summer, The Matrix, and half of Hollywood, powered by Wayans-family comedy and the breakout of Anna Faris. It opened to $42.3 million — the biggest R-rated opening weekend ever at the time — and taught the 2000s that no movie was safe from a spoof.
"Weird Al" Yankovic
The king of musical parody, Alfred Matthew Yankovic turned accordion jokes and lyrical hijinks into a decade-long MTV empire. He made fun of the songs everyone loved—and everyone watched him do it.