Staff Pick

Head Over Heels Is the Overlooked Masterpiece of the Freddie Prinze Jr. Rom-Com Era

By Mandi Bierly

She’s All That and Summer Catch might be better known but this mystery-romance is the one to watch.

Coming off the success of slasher film I Know What You Did Last Summer and its 1998 sequel, Freddie Prinze Jr. starred in five romantic comedies in three years: 1999’s She’s All That, 2000’s Down to You and Boys and Girls, and 2001’s Head Over Heels and Summer Catch. While Head Over Heels proved least popular at the box office, grossing just $10 million, it’s big-swing plot is just crazy enough to hold up.

Monica Potter (a future Golden Globe nominee for NBC’s Parenthood) stars as Amanda, a woman who always picks the wrong guy, such as the live-in boyfriend (Timothy Olyphant alert!) she discovers having sex with a model at the start of the film. Amanda restores Renaissance paintings at the Met, and lays out the metaphor for us: in beautiful art, unlike in messy life, love can last forever. In need of a new home, Amanda becomes roommates with the last four non-smoking models in New York City — who live in a huge, agency-provided apartment and rent out a closet-sized bedroom for spending cash. (Not that they ever need to spend money since men literally line up outside their front door for the chance to take them out.)

While it would have been easy to make the models cruel and unlikable for laughs, sweet but airheaded Aussie Candi (Sarah Murdoch), tough-talking Russian Roxana (Ivana Milicevic), gold digger Jade (Shalom Harlow), and smart and savvy Holly (Tomiko Fraser) win viewers over early with their support of Amanda’s weak-kneed crush on the sexy neighbor across the street, fashion executive Jim (Prinze).

The ladies can look into Jim’s apartment from their living room, and it’s not all shirtless pull-ups. Amanda watches him lower the blinds and appear to strike a woman dead with a bat. The police clear Jim, but before Amanda keeps her date with him, she decides to investigate herself — with the help of her new friends.

So where’s the comedy? Director Mark Waters (who’d go on to helm Freaky Friday and Mean Girls) does his best to capitalize on the success of the Farrelly Brothers’ raunchy R-rated 1998 rom-com There’s Something About Mary: there’s a Great Dane named Hamlet who humps Amanda, subversive punchlines about Candi’s uncle showing too much interest in her when she was young (that part does not hold up), potty humor that’s aurally and visually graphic, and sex jokes that are surprisingly racy for a PG-13 flick.

With its unexpected mix of references, Head Over Heels is the must-see in Prinze’s catalog.