Suggestions by @rwhite18

The Bone Collector (Movie)

as 1999 in Pop Culture Throughout the Years

Big Daddy

as 1999 in Pop Culture Throughout the Years

The Blair Witch Project

as 1999 in Pop Culture Throughout the Years

The Virgin Suicides

as 1999 in Pop Culture Throughout the Years

Varsity Blues

as 1999 in Pop Culture Throughout the Years

Boys Don't Cry

as 1999 in Pop Culture Throughout the Years

Never Been Kissed

as 1999 in Pop Culture Throughout the Years

Jawbreaker

as 1999 in Pop Culture Throughout the Years

Girl, Interrupted

as 1999 in Pop Culture Throughout the Years

Ratcatcher (1999)

as 1999 in Pop Culture Throughout the Years

Fish Tank

as 2009 in Pop Culture Throughout the Years

The Vanishing (1988)

as 1988 in Pop Culture Throughout the Years

Spring, Summer, Fall, Winter... and Spring (2003)

as 2003 in Pop Culture Throughout the Years

A Tale of Two Sisters (2003)

as 2003 in Pop Culture Throughout the Years

Memories of Murder (2003 film)

as 2003 in Pop Culture Throughout the Years

Oldboy (2003)

as 2003 in Pop Culture Throughout the Years

Signs

as 2002 in Pop Culture Throughout the Years

Angel (TV show)

as 1999 in Pop Culture Throughout the Years

Ewan McGregor

as Harry Tuttle in Brazil (2005)

Oliver Jackson-Cohen

as Bruce Wayne in Batman: Caped Crusader