Character Movie Actor Tom (500) Days of Summer Joseph Gordon-Levitt Patrick Verona 10 Things I Hate About You Heath Ledger Matt Flamhaff 13 Going on 30 Mark Ruffalo Jake Ryan 16 Candles Michael Schoeffling Henry Roth 50 First Dates Adam Sandler Jake Brigance A Time to Kill Matthew McConaughey Marty McFly Back to the Future Michael J. Fox Joe Bend It Like Beckham Jonathan Rhys Meyers Officer Rhodes Bridesmaids Chris O'Dowd Mark Darcy Bridget Jones's Diary Colin Firth Crash Davis Bull Durham Kevin Costner James Bond Casino Royale Daniel Craig Josh Clueless Paul Rudd Jacob Palmer Crazy Stupid Love Ryan Gosling Sebastian Valmont Cruel Intentions Ryan Phillippe John McClane Die Hard Bruce Willis Johnny Castle Dirty Dancing Patrick Swayze Ferris Bueller Ferris Bueller's Day Off Matthew Broderick Peter Bretter Forgetting Sarah Marshall Jason Segel Jason Friends With Kids Adam Scott Will Hunting Good Will Hunting Matt Damon Neil He's Just Not That Into You Ben Affleck Ben Barry How to Lose a Guy in Ten Days Matthew McConaughey Peter Klaven I Love You, Man Paul Rudd Indiana Jones Indiana Jones & The Last Crusade Harrison Ford Jerry Maguire Jerry Maguire Tom Cruise Jake Schram Keeping the Faith Ben Stiller Tristan Ludlow Legends of the Fall Brad Pitt Enjolras Les Miserables Aaron Tveit Mark Love Actually Andrew Lincoln Karl Love Actually Rodrigo Santoro Prime Minister Love Actually Hugh Grant Gil Midnight in Paris Owen Wilson Christian Moulin Rouge Ewan McGregor Sam Coulson Never Been Kissed Michael Vartan Jack Kelly Newsies Christian Bale Rusty Ryan Ocean's Eleven Brad Pitt Danny Ocean Ocean's Eleven George Clooney Derek Save the Last Dance Sean Patrick Thomas Lloyd Dobler Say Anything John Cusack Pat Solitano Silver Linings Playbook Bradley Cooper Sam Baldwin Sleepless in Seattle Tom Hanks Jake Perry Sweet Home Alabama Josh Lucas Guy Patterson That Thing You Do! Tom Everette Scott Doug Dorsey The Cutting Edge D.B. Sweeney Billy Costigan The Departed Leonardo DiCaprio Dignam The Departed Mark Wahlberg Miles The Holiday Jack Black Graham The Holiday Jude Law Paul The Kids Are All Right Mark Ruffalo Lon Hammond The Notebook James Marsden Noah The Notebook Ryan Gosling Westley The Princess Bride Cary Elwes Dickie Greenleaf The Talented Mr. Ripley Jude Law Doug MacRay The Town Ben Affleck Jack Dawson Titanic Leonardo DiCaprio Maverick Top Gun Tom Cruise Harry Burns When Harry Met Sally Billy Crystal