10 Movies Like "10 Things I Hate About You" (1999)

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10 Movies You'll Love!

10 Things I Hate About You is an American romantic comedy film released on March 31, 1999. The movie’s top-billed cast includes Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt. Based on the late 16th-century play, ‘The Taming of the Shrew,’ written by William Shakespeare, 10 Things I Hate About You is a story of love and dating in a high school setting. It is directed by Gil Junger, whose leadership made the movie a big hit.

Below are movies like “10 Things I Hate About You” that will surely remind you how fun high school life is.

1. She's All That

Release Date: January 29, 1999

Director: Robert Iscove

Cast: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard

Zack Siler is a high school hunk and the school’s favorite. But when his pretty, popular but mean girlfriend, Taylor Vaughn, dumps him publicly for a volleyball player, frustrated Zack is pushed into a bet. The bet is made by his best friends: that is to turn the nerdy, unattractive Laney Boggs into a beautiful prom queen. During the process of transforming her, Zack soon finds himself falling for her. But it only leads to other hitches, from both their friends and enemies.

2. Clueless

Release Date: July 19, 1995

Director: Amy Heckerling

Cast: Alicia Silverstone, Stacey Dash, Brittany Murphy

Cher Horowitz is one of the most popular sophomores in school. With her best friend Dionne, she is able to make two of their single teachers date. When she and Dionne succeed in their first matchmaker play, Cher takes a student named Tai under her wings. Tai is a shy, ‘clueless’ transferee. Cher finds Tai a boyfriend but soon realizes that she wants a boyfriend herself. During her first attempts, she fails, until one day, when she’s least expecting, the man of her dreams suddenly appears.

3. Get Over It

Release Date: March 9, 2001

Director: Tommy O'Haver

Cast: Kirsten Dunst, Ben Foster, Melissa Sagemiller

Popular high school hottie and basketball star, Berke Landers, gets dumped by Allison, his long-time girlfriend. Upset, Berke starts losing his prowess inside the basketball court. With the help of Kelly, his best friend Felix's cute sister, he keeps an eye on his ex, even following her into the school's musical for spring. But during their ‘undercover work,’ Berke develops a special feeling for Kelly and soon realizes that he’s actually getting over his ex.

4. Can't Hardly Wait

Release Date: June 12, 1998

Directors: Harry Elfont, Deborah Kaplan

Cast: Jennifer Love Hewitt, Ethan Embry, Charlie Korsmo

It is a graduation party, and everyone has his own fun agenda for the entire night. Preston, who has been hiding his feelings for Amanda for years, has only one plan for the night: to confess his feelings to the pretty cheerleader and prom queen. Amanda, however, is currently dealing with heartache after being dumped by famous Mike. Kenny, an aspiring rapper, is thinking about losing his virginity. Kenny’s plans, though, are diverted by Preston’s anti-social friend, Denise. These teens must solve their high school issues before moving on to the next level in life.

5. Never Been Kissed

Release Date: April 9, 1999

Director: Raja Gosnell

Cast: Drew Barrymore, David Arquette, Michael Vartan

25-year-old Josie Gellar, a copy editor at Chicago Sun Times, is determined to leave her current job and pursue her dream: to be a reporter. It turns out that she is having the luck of her life, as her boss at Sun Times gives her an undercover task: to cover a scene in her old high school. Her funny brother gives her a make-over, transforming the nerdy journalist into an attractive woman. In school, she meets the single Sam Coulson, a teacher who enjoys complicated conversations with her. Problems arise as the publication deadline approaches. Josie is soon caught between protecting her undercover job and achieving her dream.

6. Save The Last Dance

Release Date: January 12, 2001

Directors: Thomas Carter

Cast: Julia Stiles, Sean Patrick Thomas, Kerry Washington

Sara is a white Mid-Western young woman who dreams of becoming a ballerina. However, misfortunes and her mother’s death hinder her to achieve that dream. She moves to Chicago with her father, who lives in an area predominantly occupied by Black neighborhoods. She transfers to a new school, and being one of the very few White students there, Sara has become quite popular, particularly among the male students. Later, she meets her friend Chenille’s elder brother, Derek, and falls in love with him. Until she discovers Derek’s terrible past…

7. Ferris Bueller's Day Off

Release Date: June 11, 1986

Director: John Hughes

Cast: Matthew Broderick, Alan Ruck, Mia Sara

Wise, high school student Ferris Bueller is serious when he says that he will take a day off from all the studying. He is able to construct a clever plan to pull it off. He even asks his school buddy Cameron to borrow his father's expensive Ferrari. With Sloane, his girlfriend, Ferris heads off to Chicago to enjoy the day. Ed Rooney, the school principal, knows exactly what Ferris is up to. Rooney also knows that this is not the first time Ferris takes a day off. Rooney is determined to catch Ferris out, and Ferris is as much decided to play with him.

8. Summer Catch

Release Date: August 24, 2001

Director: Michael Tollin

Cast: Freddie Prinze Jr., Jessica Biel, Fred Ward

Ryan Dunne is a well-mannered high school boy who has a big dream: to be a successful baseball player. But with the kind of life he has, he sometimes loses hope. He has to work hard for dad Sean's farm, mowing lawns each day. His elder brother, Mike, always scolds him for his lack of ambition and for letting a big opportunity, a college baseball scholarship, pass. That’s the same chance Mike had to turn down due to disability. One day, a rich girl and her family arrive for a summer vacation. Things start getting complicated when Ryan falls for her.

9. A Midsummer Night's Dream

Release Date: May 14, 1999

Director: Michael Hoffman

Cast: Kevin Kline, Michelle Pfeiffer, Rupert Everett

Lysander and Demetrius both fall in love with Hermia, who wants no one but Lysander. Hermia's father, however, wants her to marry Demetrius. Helena is in love with Demetrius and wants him badly. Hermia and Lysander plan to escape from their complicated lives in the city. Demetrius, being pursued by Helena, discovers Hermia and Lysander’s plan and becomes very angry. In the woods, the head troublemaker of the King and Queen of faeries, Oberon and Titania, creates a mistake, causing people to fall in love with the first thing they see after sleeping. Love and complications collide, making the intertwining love story funny.

10. The Prince and Me

Release Date: April 2, 2004

Director: Martha Coolidge

Cast: Julia Stiles, Luke Mably, Miranda Richardson

Manitowoc farm girl, Paige, is a pre-med student at the University of Wisconsin. There, she meets Eddie, a Denmark-born student. Paige, at first, dislikes him. Eventually, they get close, become friends, and fall in love. Paige soon discovers that the ordinary man she has fallen in love with is none other than Crown Prince Edvard. When King Haraald becomes sick, Edvard goes back to Copenhagen. Paige follows him, and Edvard introduces her to his family. Edvard’s family dislikes her at first but soon accepts her. The couple gets engaged, but Paige, wanting to be a doctor, returns to school. Edvard follows her with a plan.