Millennium Movies Every Teen Should Watch — PICS

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August 19, 2017 10:59AM EDT

1 of 13

’10 Things I Hate About You’ (1999)

’10 Things I Hate About You’ (1999) — Kat Stratford (Julia Stiles) is beautiful, smart and quite abrasive to most of her fellow teens, meaning that she doesn’t attract many boys. Unfortunately for her younger sister, Bianca (Larisa Oleynik), house rules say that she can’t date until Kat has a boyfriend, so strings are pulled to set the dour damsel up for a romance. Soon Kat crosses paths with handsome new arrival Patrick Verona (Heath Ledger). Will Kat let her guard down enough to fall for the effortlessly charming Patrick? (Courtesy of Touchstone Pictures)

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’40 Days and 40 Nights’ (2002)

’40 Days and 40 Nights’ (2002) — Matt Sullivan’s (Josh Hartnett) last big relationship ended in disaster and ever since his heart’s been aching and his commitment’s been lacking. Then came Lent, that time of year when everybody gives something up. That’s when Matt decides to go where no man’s gone before and make a vow: No sex. Whatsoever. For 40 straight days. At first he has everything under control. That is until the woman of his dreams, Erica (Shannyn Sossamon), walks into his life. (Courtesy of Universal Pictures)

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‘American Pie’ (1999)

‘American Pie’ (1999) — A riotous and raunchy exploration of the most eagerly anticipated — and most humiliating — rite of adulthood, known as losing one’s virginity. In this hilarious lesson in life, love and libido, a group of friends, fed up with their well-deserved reputations as sexual no-hitters, decide to take action. (Courtesy of Universal Pictures)

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‘Can’t Hardly Wait’ (1998)

‘Can’t Hardly Wait’ (1998) — School’s out, and an entire graduating class — from football stars and cool girls to complete nerds — gathers at a wealthy classmate’s home for a party. There, the artistic Preston (Ethan Embry) hopes to move in on Amanda (Jennifer Love Hewitt), the beauty he has admired from afar for years. Dorky William (Charlie Korsmo) schemes to pay back meathead Mike (Peter Facinelli) for years of bullying, and would-be rapper Kenny (Seth Green) gets locked in a room with snarky Denise (Lauren Ambrose). (Courtesy of Columbia Pictures)

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‘Cruel Intentions’ (1999)

‘Cruel Intentions’ (1999) — Annette (Reese Witherspoon) unwittingly becomes a pawn in Sebastian’s (Ryan Phillippe) and Kathryn’s (Sarah Michelle Gellar) deliciously diabolical wager of sexual conquest when she writes an article in Seventeen Magazine about how she intends to stay pure until she marries her boyfriend. However, Sebastian gets more than he bargained for as he attempts to woo Annette into his bed. (Courtesy of Columbia Pictures)

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‘Drive My Crazy’ (1999)

‘Drive My Crazy’ (1999) — Nicole (Melissa Joan Hart) and Chase (Adrian Grenier) live next door to each other but are worlds apart. However, they plot a scheme to date each other in order to attract the interest and jealousy of their respective romantic prey. But in the mist of planning a gala centennial celebration, Nicole and Chase find that the one they always wanted was closer than they ever thought. (Courtesy of 20th Century Fox)

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‘Here On Earth’ (2000)

‘Here On Earth’ (2000) — Kelley Morse (Chris Klein), who is cocky and brash, normally would never have crossed paths with the residents of a small town near his posh private school. But when he races his new car against a local boy and destroys a diner, he is sentenced to rebuild the diner and falls in love with the owner’s daughter (Leelee Sobieski). (Courtesy of Fox 2000 Pictures)

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‘Jawbreaker’ (1999)

‘Jawbreaker’ (1999) — When an exclusive clique of teenage socialites accidentally murders their best friend, Liz (Charlotte Ayanna), on the morning of her birthday, the three girls responsible — Courtney (Rose McGowan), Julie (Rebecca Gayheart) and Marcie (Julie Benz) — conspire to hide the truth. As the trio make over nerdy reject Fern Mayo (Judy Greer) and groom her to take Liz’s place, crack police Detective Vera Cruz (Pam Grier) launches an investigation that will turn Reagan High School upside down. (Courtesy of TriStar Pictures)

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‘Never Been Kissed’ (1999)

‘Never Been Kissed’ (1999) — Josie Geller (Drew Barrymore), a baby-faced junior copywriter at the Chicago Sun-Times, must pose as a student at her former high school to research contemporary teenage culture. With the help of her brother, Rob (David Arquette), Josie infiltrates the inner circle of the most popular clique on campus. But she hits a major snag in her investigation — not to mention her own failed love life — when she falls for her dreamy English teacher, Sam Coulson (Michael Vartan). (Courtesy of 20th Century Fox)

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‘Save The Last Dance’ (2001)

‘Save The Last Dance’ (2001) — Sara (Julia Stiles) is moved from a small Midwestern town to the south side of Chicago when her mother dies in a car accident, and must live with her father. She soon falls for an African American teenager (Sean Patrick Thomas) at her new high school and he has less than an idyllic past. They share a love for dance (ballet and hip hop respectively) and together they tackle the problems that go with an interracial relationship. (Courtesy of Paramount Pictures/MTV)

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‘She’s All That’ (1999)

‘She’s All That’ (1999) — Sara (Julia Stiles) is moved from a small Midwestern town to the south side of Chicago when her mother dies in a car accident, and must live with her father. She soon falls for an African American teenager (Sean Patrick Thomas) at her new high school and he has less than an idyllic past. They share a love for dance (ballet and hip hop respectively) and together they tackle the problems that go with an interracial relationship. (Courtesy of FilmColony)

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‘Sugar & Spice’ (2001)

‘Sugar & Spice’ (2001) — When Jack (James Marsden) and Diane (Marley Shelton) find themselves in an unexpected adult situation, the A-Squad comes to their rescue. In order to help their friend Diane, the A-Squad goes where no cheerleader has gone before: taking on a little after-school project known as bank robbery. But the A-Squad does things their way — with sugar and spice — forever changing their friendship, their future and the nation’s notion of teen spirit. (Courtesy of New Line Cinema)

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‘The Prince & Me’ (2004)

‘The Prince & Me’ (2004) — Paige Morgan (Julia Stiles) is a focused premed student who becomes intrigued by Eddie (Luke Mably), a wealthy Danish student. Despite Eddie’s initially boorish behavior, Paige falls for him, only to discover that his father (James Fox) and mother (Miranda Richardson) are the king and queen of Denmark, and he is heir apparent to the throne. As Eddie adjusts to American life, and Paige gets used to her beau being a future king, the two must decide if their romance is something that can last. (Courtesy of Lionsgate)

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