That’s right, a cartoon ogre’s on the list. Although this 2001 Oscar-winning adventure is kid-centric, its pop culture references and unique humor set the bar for animated films with all-ages appeal.

The film that launched a million bad imitations became a cultural phenomenon in 2004, with Jon Heder’s high school nerd carrying this quirky comedy into neoclassic territory.

Legendary is right. Packed with polyester and preposterous hair, this 2004 comedy about a chauvinistic 1970s TV reporter was glory bound. Rife with ridiculousness, it has a rep for being Will Ferrell’s funniest.

In 2001, this imaginative award-winning tale first transported us into the life of Audrey Tatou’s French gamine, and it remains a landmark of beguiling and unforgettable charm.

As 2007 pushed out one surprise pregnancy comedy after another, this particular lo-fi sleeper hit the box office hard with its heartwarming hilarity.

Yes, it’s a story about horny high schoolers, but this 2007 romp starring Jonah Hill and Michael Cera elevated the genre, overshadowing goofy teen farces of the past.

All hail the bend-and-snap. With Reese Witherspoon as flighty but fierce Elle Woods, this 2001 story of blond ambition is still a fave.

A Kazakh reporter exceeds the boundaries of decency as he crisscrosses the United States. Not for the weak of heart, this award-winning mockumentary established itself in the modern comedy vanguard.

Countless diary pages, two Englishmen, and one very large pair of granny panties. It must be a classic. We never tire of this 2001 Helen Fielding book adaptation—humiliating moments and all.

The 2007 baby boom that also bore Knocked Up was led by this Oscar-winning tale of a pregnant high school student.