Having spent some serious time looking over all of Shakespeare's characters and motivations, we decided we would partake in the general enthusiasm towards sports and create a fantasy draft for Shakespearean characters, nominating the ideal actor or actress to play each role.  After several long nights of excel spreadsheets and tears, we are happy to present our findings to you:

Leading male: Ole Leonardo di Caprio - as far as the comedies go, none of Shakespeare's leading males have to be good at acting.  In fact, many of the roles are just place holders for plot development.  We find that this matches very well with Leo's skill set - just look pretty.
Leading female: Young Leonardo di Caprio - as all female roles were played by boys during Shakespeare's era, we thought it would be best to take a traditional approach and cast a youthful Leo in this role.  It's hard to say when exactly he shed his boyish charm in place of a leading male look (although some would say they are still waiting for this transition), but one thing is for sure, the screeching pubescent voice of the Titanic Leo is exactly what we need to pull this casting off.
Jealous angry black man: Samuel L. Jackson - we think this pretty much stands on it's own.
Guy that looks like girl: Ryan Phillipe
Girl that looks like guy: Hillary Swank
Angsty Teenager (male): Owen Wilson (suicidal angst), Michael Serra (loveable angst), Paul Dano (emo angst) - this was a tough one, and hence the three way tie.  Each actor has a unique approach to the "angsty teenager" role that we couldn't pass on.  Michael Serra offers a loveable angst that manifests itself as a stuttering, bumbling, affectionate "you're such a great friend that I have no interest in sleeping with" way.  Paul Dano presents the quintessential emo angst that would rival even the most depressed NYU student or Williamsburg hipster.  His performance in Little Miss Sunshine made even the most pacifistic hipsters want to join the airforce so they could have the opportunity to be even more miserable than they already are.  Owen Wilson: this was a wildcard.  Because of age you'd think that he wouldn't have made the cut, but rest assured he's the black horse not to be overlooked.  The fact that Owen Wilson had so much angst that he actually attempted to kill himself makes him the perfect candidate for the part.  Sure, he's a little old, but we think some true magic could happen if you put him on stage (with a razor blade).
Angsty Teenager (female): That Girl from "Juno." - we apologize for not knowing her name, nor taking the time to look it up.  We didn't like her enough in Juno to really pay attention to her as anything other than "that pregnant chic in that movie that Michael Serra was in."
Hamlet: Kenneth Branagh - self important, attention hungry, whiny.
Ophelia: Angelina Jolie - both Ophelia and Angie are crrrr-aaazy (she used to carry around a vial of Billy Bob Thorton's blood for Christ's sake!). 
Macbeth: James McAvoy - he's the only Scottish actor we know...or at least he played a Scottsman in that movie with Forrest Whitaker (that guy is sweet).
Lady Mcbeth: Glen Close - scariest actress known to mankind.
Idiot Savante: Zach Braff - funny in an "I'm surprised you can actually form a sentence" sort of way.  We find ourselves laughing with/at him and wondering "why?"  It's not that he isn't funny, he's quite funny, we just don't know why that is.
Falstaff/Bottom: John Goodman - he's damn funny.
Talentless Clown (who dies): Adam Sandler
King: George Clooney - he's the king of hollywood (and womanizing) so why not be the king?
Prince: Brad Pitt - what sucks most about being prince is that you are second fiddle to the king, like a little sidekick that is always one step behind the big man.  True to form, with Clooney as king, we had to put Pitt as prince.  Don't worry Brad, Hal got his chance too.

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