Remember the late 90s? It was a time of frosted tips, dial-up internet, and surprisingly earnest romantic comedies. And right there, smack dab in the middle of it all, was Never Been Kissed. This movie, released in 1999, is like a warm hug from your favorite comfortable sweater. It’s funny, it’s sweet, and it’s got a cast that just makes you smile.
At the heart of it all is Drew Barrymore, who plays Josie Geller. Now, Josie is a bit of a mess. She’s a reporter who’s never really lived the glamorous life she imagined. In fact, she’s so uncool, she’s never even been kissed! Can you imagine? So, when her editor assigns her a story to go undercover as a high school student, it's her chance to relive her awkward teenage years and, maybe, finally get that first kiss.
Going back to high school as an adult? Talk about a wild premise! Josie’s trying to blend in, but of course, she sticks out like a sore thumb. She’s awkward, she’s trying way too hard, and it’s just delightful to watch. Drew Barrymore truly shines here. She’s got this incredible ability to be both hilarious and completely endearing. You root for Josie from the get-go. You want her to succeed, to find her confidence, and yes, to get kissed!
But Josie isn't navigating this bizarre high school world alone. She's got a whole crew of quirky characters surrounding her, and the cast of Never Been Kissed is just bursting with talent. Let's talk about her wingman, her brother, Robbie Geller, played by Michael Vartan. He’s Josie’s older brother who’s a bit protective and a lot more put-together. He’s the one who helps her prepare for her undercover mission, offering advice that’s both practical and, let’s be honest, sometimes hilariously off the mark. His scenes with Drew are gold. There's this easy chemistry between them that makes their sibling dynamic feel so real.
Then there are Josie’s best friends, the resident cool kids who take her under their wing. There's the totally awesome and slightly intimidating Aldys, played by the fabulous Molly Shannon. Molly Shannon is a comedic genius, and even in a supporting role, she steals every scene she’s in. Her character is just so over-the-top and full of life. And let's not forget the effortlessly cool guys, Guy and his crew, led by the charismatic David Arquette as Rob Geller's best friend. David Arquette brings this laid-back coolness to the role, and his interactions with Josie are a constant source of amusement.
But the real magic, the secret sauce that makes Never Been Kissed so special, is how it handles the high school experience. It’s not all about fitting in. It’s about finding your people, the ones who accept you for who you are, even if you’re a little weird. Josie’s journey is about embracing her true self. She starts off trying to be someone she’s not, but she eventually finds her confidence by being unapologetically Josie. And that’s a message that really resonates.
The movie also has a fantastic supporting cast that adds so much color. You’ve got the intimidating yet secretly kind English teacher, Mr. G. K. B. (or “Mr. G” as he’s known), played by the always brilliant Steve Roles. He’s the kind of teacher every student wishes they had – challenging but inspiring. And the principal, played by the fantastic John C. Reilly, who pops up in unexpected moments and brings his signature comedic timing. It’s like a treasure hunt of familiar faces, each one bringing their A-game.
What makes Never Been Kissed so rewatchable? It’s that perfect blend of humor and heart. You’ll laugh out loud at Josie’s misadventures, her attempts to speak teen slang, and her general awkwardness. But you’ll also feel a pang of sympathy for her, and you’ll cheer her on as she navigates the minefield of high school cliques and crushes. It taps into that universal feeling of wanting to belong and finding your place in the world.
And then there's the romance! Oh, the romance. It’s a slow burn, filled with stolen glances and misunderstandings. You’re just waiting for it to happen, for that big moment. And when it does, it’s absolutely swoon-worthy. The scene where Josie finally gets her moment with her dream guy... well, let's just say it's iconic. It’s the kind of scene that makes you believe in fairy tales, even if they’re set in a high school cafeteria.
The fashion in Never Been Kissed is also a huge part of its charm. We’re talking quintessential late 90s style. Think platform shoes, chokers, and lots of denim. It’s a nostalgic trip back in time, and it’s fun to see the characters dressed in all their 90s glory. It adds to the overall feel-good vibe of the movie.
Ultimately, Never Been Kissed is more than just a romantic comedy. It’s a story about second chances, about embracing your awkwardness, and about finding the courage to be yourself. The cast, led by the radiant Drew Barrymore, is what truly brings this story to life. They are all so incredibly charming and funny, and they make you fall in love with their characters, flaws and all. If you’re looking for a movie that’s guaranteed to make you smile, laugh, and maybe even shed a happy tear or two, then Never Been Kissed is definitely worth a watch. It’s a classic for a reason, and it still holds up today!
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