Film

Drive Me Crazy

Name: Drive Me Crazy
Genre: Romance, Comedy, Drama
Released: 1999
Cast: Melissa Joan Hart, Adrian Grenier, Susan May Pratt, Kris Park, Ali Larter

Romantic comedy
Light-hearted

A 1999 teen romance about two neighbors who fake-date to make their crushes jealous, only to discover they're perfect for each other. It's fizzy, earnest, and entirely of its moment—a pre-smartphone high school rom-com that believes in grand gestures and genuine connection. For anyone who loves the specific texture of late-90s teen movies.

TMDb rating

3.3

If you liked this

10 Things I Hate About You1999

Released the same year with similar DNA: teens scheming, unexpected romance, a school dance climax. Sharp dialogue, genuine chemistry between leads, and it captures that specific energy of '90s teen movies before irony took over.

But The Stratford-upon-Avon setup feels contrived, and it leans hard on Shakespeare references that don't land for everyone.

Clueless1995

The gold standard of teen rom-coms. Cher's makeover scheme parallels Nicole and Chase's plan, but it's smarter, funnier, and Alicia Silverstone is a revelation. The writing is genuinely witty without winking at the camera.

But Its vision of Beverly Hills can feel dated, and the tone sometimes skids between satire and sincerity in jarring ways.

She's All That1999

A fellow '99 teen romance with a similar makeover-and-schemes plot. Freddie Prinze Jr. and Rachael Leigh Cook have undeniable chemistry, and it's unapologetically earnest about its own ridiculousness in a way that's oddly charming.

But The premise—bet you can turn any girl into prom queen—hasn't aged well, and the makeover plot is fundamentally shallow even as entertainment.

Not sure tonight? Get a pick in a minute, starting from Drive Me Crazy

The wildcard

Something you would not have found on your own.

Wet Hot American Summer2001

Both are teen-ensemble films about attraction and deception during a summer/school event, but Wet Hot treats the conventions as material to dismantle rather than honor.

A parody of exactly the kind of movie Drive Me Crazy is, but with a cast of comedians who went on to define comedy (Paul Rudd, Amy Poehler, Bradley Cooper). It's absurdist, filthy, and brilliantly constructed as both homage and mockery. The fake-romance plots are there, but weaponized for comedy.

But If you loved Drive Me Crazy for its sincerity, this will feel like a roast of everything you cherish. It's deliberately terrible in places, which requires a specific sense of humor.

A Cinderella Story2004

This one recasts the fake-identity gambit as a modern fairytale. Hillary Duff and Chad Michael Murray sell the absurdity with genuine warmth, and there's real heart underneath the fantasy.

But It's sickly sweet in places, and the stepmother subplot is painfully one-note.

Never Been Kissed1999

Another '99 entry that understands earnestness isn't embarrassing. Drew Barrymore's reporter going undercover in high school feels like a spiritual cousin to Drive Me Crazy's deception plot, but with more emotional depth.

But It's very long, and the pacing sags in the middle. Some of the high school jokes feel like they're from an earlier era even for 1999.

Can't Hardly Wait1998

A lesser film than the above, but it captures that same pre-millennial teen energy perfectly. An ensemble cast, an epic party, everyone chasing the wrong person until they realize what's in front of them.

But The plot is thin, the jokes are uneven, and it's very much a product of its specific moment, which can feel dated now.

Saved!2004

A teen comedy with real satirical bite underneath the romance. The scheme-and-deception plot serves actual character exploration, and it's funny without punching down at anyone.

But Some will find the religious satire heavy-handed, and the tone can feel preachy even when it's making good points.

The Princess Diaries2001

Anne Hathaway's wide-eyed charm and the fish-out-of-water premise have genuine warmth. It's comfort-food romance for teen audiences, and it earns its sincerity through earnest performances.

But The makeover plot is paper-thin, and there's a dated corporate-princess fantasy underlying the whole thing.

Bring It On2000

Kirsten Dunst leading a cheerleading movie that's smarter than it has any right to be. It's got scheming, romance, competition, and actual commentary on race and class hiding under the pom-poms.

But Some of the dance sequences feel endless, and the racial themes, while present, are handled without enough depth.

Moonlight2016

Both explore the masks we wear and the proximity to truth: one asks the question joyfully, the other asks it with profound sorrow.

Three chapters of a Black man's life, intimate and devastating. What connects it to Drive Me Crazy is the core question: how do we hide who we are, and what does it cost when we finally don't? It's a complete inversion in tone and weight, but the emotional architecture is about the same thing.

But It's slow, quiet, and demands patience. There is no lightness here, and the ending will break you rather than uplift you.