4. The 40-Year-Old Virgin (2005)
Director: Judd Apatow
Writer: Judd Apatow
Stars: Steve Carell, Catherine Keener, Seth Rogen, Paul Rudd, Romany Malco, Elizabeth Banks, Jane Lynch, Kat Dennings
Quotable: "Know how I know you're gay? You macraméed yourself a pair of jean shorts."
Fun Fact: The scene in which Carell has his chest waxed is 100 percent real.
It's hard to remember a time when Judd Apatow's brand of everyman comedy and deep roster of go-to performers weren't in vogue. It wasn't until The 40 Year Old Virgin, though, that one of Hollywood's most underappreciated creators (responsible for the unfairly cancelled TV shows Freaks & Geeks and Undeclared) finally broke through.
The 40 Year Old Virgin brought swag back to R-rated comedies, utilizing a well-crafted story and strong characters to lend undeniable credibility to some very raunchy humor. It's also the reason Steve Carell became the superstar he is today; perfectly cast, he nails every one of his awkwardly funny lines ("She was a hoe...fo sho!").