|Max Casella as Vinnie Delpino|
5. Vinnie Delpino (Max Casella in "Doogie Howser")
Vinnie was the titular character's best friend on "Doogie Howser, M.D." He was a New York accented, wise-cracking budding filmmaker and often the instigator of the mischief the two friends got into.
|Christian Bale as Jack Kelly|
4. Jack Kelly (Christian Bale in Newsies)
In the fact-based Disney movie Newsies, Jack Kelly was the leader of the "newsies" - New York-based newsboys who went on strike after Joseph Pulitzer raised newspaper costs. Back when Bale was a relatively unknown actor, he did this heavily panned flick. But critics be damned, I freakin' love this movie and I still watch it when nostalgia strikes.
3. Lane Meyer (John Cusack in Better Off Dead)
|John Cusack as Lane Meyer|
|Robert Sean Leonard as Neil Perry|
2. Neil Perry (Robert Sean Leonard in Dead Poet's Society)
Before appearing as Dr. Wilson on "House", Leonard was best known for his performance as Neil Perry, the intelligent prep school student who attempts to follow his acting dreams, much to the dismay of his father. Dead Poet's Society is an excellent film and Leonard is amazing in it.
|Jon Cryer as Duckie Dale|
1. Duckie Dale (Jon Cryer in Pretty in Pink)
All of this brings me to my #1 childhood crush, and the only Teen Beat-esque poster I had on my wall. In his pre-"Two and a Half Men" days, Cryer was best known as the unrequited love afflicted Duckie Dale. Loyal to his best friend/crush and devoted to New Wave, Duckie was the coolest geek out there and every true Pretty in Pink fan knows that Andi should have picked him over Blaine.
Honorable mentions: Duncan (Elias Koteas in Some Kind of Wonderful), Ferris Bueller and Cameron Fry (Matthew Broderick and Alan Ruck in Ferris Bueller's Day Off), and Inigo Montoya (Mandy Patinkin in The Princess Bride)