Head Over Heels (2001) Cast & Crew

Overview · Where to watch · Cast & crew · Reviews

Directed by Mark Waters.

Cast

• Monica Potter as Amanda Pierce
• Freddie Prinze Jr. as Jim Winston
• Shalom Harlow as Jade
• Ivana Miličević as Roxana
• Sarah Murdoch as Candy
• Tomiko Fraser as Holly
• China Chow as Lisa
• Timothy Olyphant as Michael
• Stanley DeSantis as Alfredo
• Erin-Marie Dykeman as 10 Year-Old Amanda
• James Kirk as Tommy
• Elysa Hogg as Tommy's Girlfriend
• Kristina Lewis as 17 Year-Old Amanda
• Ben Silverman as Charlie
• Sam MacMillan as Charlie's Date
• Jay Brazeau as Halloran / Strukov
• Raoul Ganeev as Harold
• Brendan Beiser as Ellis
• Jody Thompson as Party Girl
• Brenda Schad as Michael's Lover
• Betty Linde as Polly
• Alex Doduk as Boy with Crutches

Crew

• Mark Waters — Director
• John J. Strauss — Writer
• Ed Decter — Writer
• Ron Burch — Writer
• David Kidd — Writer
• Mark Plummer — Director of Photography
• Randy Edelman — Original Music Composer
• Robert Simonds — Producer

Movies like Head Over Heels

If you enjoyed Head Over Heels, these movies have a similar feel:

• Addicted to Love (1997)
• She's Funny That Way (2015)
• The Broken Hearts Gallery (2020)
• Your Place or Mine (2023)
• Bullets Over Broadway (1994)
• Happy Together (1989)
• The Wrong Paris (2025)
• Isn't It Romantic (2019)
• White Chicks (2004)
• Yoh! Bestie (2026)
• Relationship Goals (2026)
• Manhattan Murder Mystery (1993)

Can't decide what to watch?

FlickPicker recommends movies from your own taste and the services you subscribe to, and Pick Together lets a whole group vote on tonight's pick. Try the free random movie generator, find movies with AI, or browse trending movies.

Download FlickPicker on the App Store   Explore the iPhone app