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We’re coming down the final stretch on our Streamys Odds posts and this one might get controversial as we tackle some of the big awards for individuals. Up now are the Best Writing and Best Directing awards for a comedy web series.  To the board we go…

Best Writing for a Comedy Web Series

David Wain (Wainy Days) 4:1 (Will Win)
Felicia Day (The Guild) 4:1
Jason Sklar, Randy Sklar, Eric Friedman, Matt Price (Back on Topps) 6:1 (Should Win)
Chris Smith, Jordan Riggs, Jessie Gaskell, Jack De Sena, Jim Brandon, Brian Singleton, Mark Stewart Iverson (Dorm Life) 10:1
Tony Janning, Sandeep Parikh (The Legend of Neil) 10:1

Last year’s comedy writing award went to the Dr. Horrible team, which guarantees us a new winner in 2010. It’s quite notable that this year’s nominees are entirely composed of web series that have at least one season.  The smart money, as always, is on the biggest names, with David Wain’s star-filled quest for love narrowly earning our ‘Will Win’ prediction over Felicia Day.

The wild card is that Wain’s comedy might lose voters because it’s so hard to pin down. Even dedicated fans might not be able to connect at times with his alternating silly, weird, and quite adult humor.  But there are some genuinely amazing moments, including a two-part musical episode to finish the season.  All in all though, The Guild is a much more even show. While the third season’s arc is fairly predictable, Felicia Day’s characters are well written, giving each actor some great individual moments throughout.

Back on Topps is another strong candidate given the comedic chops of the Sklar brothers, but I have to question how many Streamys voters are also big enough sports fans to appreciate some of the fantastic obscure athlete references (Doug Minckiewicz and Shareef Abdur-Rahim in one episode!).  However, it sits in a great spot to capitalize if Wain and Day split the vote.

Representing the underdogs, Dorm Life’s writing staff is the most dangerous due to its adept juggling of a huge cast for a web series.  Best Ensemble Cast might be the better award for it in that respect, but there’s no doubt it took talent to handle so many unique characters.  The Legend of Neil will be working with similar odds, but it also has one of the more unique tongue-in-cheek tones on the web.  Given some of the more unusual humor offered by the category’s other, better known comedian, it would make some sense if Neil’s writing made a connection with the voters.

Best Directing for a Comedy Web Series

Sean Becker (The Guild) 4:1 (Will Win)
James Gunn (PG Porn) 8:1
Sandeep Parikh (Legend of Neil) 10:1
Chris Smith, Mark Stewart Iverson (Dorm Life) 10:1
Scott Brown (Blue Movies) 12:1 (Should Win)

Best Director award is always a tough category to predict. It’s likely the difficulty of defining the award.  Ideally the Best Director should be given for overall artistic achievement, but is just as likely awarded for originality, degree of difficulty, financial success, or in the case of the Academy Awards, politics.  Hopefully the Streamys stick as closely as they can to the artistic merit, but there’s no denying the influences of big budgets, dedicated fan bases, celebrity guest stars, and the almighty view count.

When it comes to dedicated fan bases and view count, The Guild certainly carries a lot of weight. We picked it as the favorite for the Best Comedy Web Series award for that reason.  Sean Becker has also put together another solid season and after losing out to Joss Whedon last year, it’s very likely his year.

On the celebrity side of things, ask any horror fan about James Gunn and you’ll realize how big a name he is.  His PG Porn cast, from Nathan Fillion to Craig Robinson, is great and individual scenes are quite clever, but each episode is a one off.  To that end, the first episode revealed a joke (yes the title is accurate, this isn’t really porn) that has less impact with subsequent episodes.  It’s quite an odd nominee then for a Directing award, given that episodes are designed to recreate the poorly directed PG moments of bad late night Cinemax.  Sure, it’s successful in that goal, but it would be a shame if Hollywood veteran Gunn took home the Streamy for that accomplishment when other nominees helmed series with complete character arcs (if less views).

The Guild’s foul-mouthed cousin gets its second straight Best Director nomination and while Sandeep Parikh continues to create some very fun visuals, in particular its original Land of the Lost like world, it would be quite an upset for it to beat out The Guild.  Given the show’s tough competition in the writing category though, voters might choose to reward Sandeep Parikh in this category.

Chris Smith and Mark Stewart Iverson are serious contenders first and foremost because of their show’s enormously loyal following.  Dorm Life’s style is not unique, as it continues a now familiar tradition of emulating The Office, but at this point in the TV show’s run it’s hard to decide which now does it better. The simplicity of direct camera addresses lessens Dorm’s Life need for additional camera angles, allowing the show to be quite prolific.  The second season included 26 episodes including a two-episode finale over 30 minutes long (!!).

With the category’s second pornography related web series, Scott Brown has created a much more complete series than his Hollywood counterpart.  And in focusing the series behind the scenes, he finds some genuine moments in a ridiculous world.  Without a doubt though, Brown would be the Cinderella story with a victory here. The series is polished and professional, but does not have the immense followings of Dorm Life, Neil, or The Guild.  Is there a chance that the top four candidates split the vote and leave Blue Movies to capture the crown?  Absolutely.  And we’d certainly be excited for a fresh face accepting the award.  In fact, wouldn’t it make a lot of sense for the Streamys to throw its weight behind a brand new breakout talent? Cross your fingers…