Fresh off an unsurprisingly stellar season four of AMC’s hit show Mad Men, creator/head writer/director/all-knowing-Oz Matthew Weiner is currently busy casting his feature film debut, the romantic dramedy You Are Here. Pajiba reports that Jack Black, Matt Dillon, and Renée Zellweger are currently attached to star, and with an offer out to Rachel McAdams to join the cast as well.

Last year, we reported that Weiner was looking to cast Jennifer Aniston, Bradley Cooper, and Zach Galifianakis in the project.  However, when the film didn’t materialize as fast as Weiner was hoping, filming was pushed back to this year in lieu of scheduling issues with the filming of Mad Men.  It looks like Weiner has chosen the current hiatus between seasons four and five to get the project back on track.  For more on the film, including a plot description and which characters each actor will play, hit the jump.

You Are Here was written by Weiner during his days as a writer on The Sopranos, so one could assume that it would be a bit, ahem, dark.  However, the description actually seems much lighter than one might expect.  Pajiba says:

It’s about two roommates in their 30s, preoccupied with dodging the responsibilities and rigors of adult life. That is, until the sudden death of one of the men’s fathers, which makes his unstable son the new owner of a general store, a country home and millions of dollars worth of Amish farmland.

Black is set to play the “unstable son” (which was previously the role Galifianakis was attached to, who I would’ve loved to see in this part), with Dillon as his “skirt-chasing, hard-partying roommate”.  Zellweger is said to play Black’s sister, jealous and angry over her omission from her father’s will.  Finally, McAdams, if she accepts the part, would play the father’s widow.

This actually sounds like an intriguing/entertaining story, but I can’t help but long for the previously attached cast.  Galifianakis proved in It’s Kind of a Funny Story that he can do drama, and from a Matthew Weiner script you can be sure the film will have its fair share of dramatic scenes.  Not to mention the fact that it’s been a while since we’ve seen either Dillon or Zellwegger in anything, well, significant.  But maybe that’s a good thing.  Say what you will about Zellwegger, but her performance in Jerry Maguire was spot on, and this could put Dillon back into Singles/There’s Something About Mary endearing asshole territory.

Nevertheless, I just can’t see Weiner making a bad film (unless he decides to include creepy Glen).  This season’s Don/Peggy episode “The Suitcase” was one of the best hours of television in the history of the medium, and the show’s shown no sign of creatively dwindling over the years.  It’s hard to see him fumbling his feature film debut.