Chicago has a rich history of film criticism: the late Gene Siskel, the Chicago Sun Times’ Richard Roeper and, of course, the brilliant and iconic Roger Ebert. For it’s first-ever Oscar picks post, Your Industry Insider turned to our own favorite Chicago-area critic, Danny King of The King Bulletin. When Danny is not busy in his high school classes, he sees every movie that comes out and his blog is equal parts enthusiasm and appreciation for the art form overall and critical assessment of each individual film. We think his Oscar picks reflect both those sides of him and we hope you enjoy them as much as we did.

Best Cinematography

Will Win: Barry Ackroyd, THE HURT LOCKER

Should Win: Christian Berger, THE WHITE RIBBON

This category is a tough one to predict, and by no means is Barry Ackroyd the clear favorite. Mauro Fiore (for AVATAR) is most-likely his strongest adversary, although I just think more people will prefer the gritty, mockumentary style of Ackroyd’s work. Although I wasn’t the biggest fan of Michael Haneke’s THE WHITE RIBBON, I will be the first to admit that Berger’s use of black and white cinematography is a remarkable achievement and is, in fact, the main reason to see the film. I don’t think any other nominee had as much of an impact of their film’s final product than Berger did, and for that reason, he’s the most deserving in the category, in my opinion.

Best Original Screenplay

Will Win: Quentin Tarantino, INGLOURIOUS BASTERDS

Should Win: Quentin Tarantino, INGLOURIOUS BASTERDS

Many are sure to disagree with me, but I truly believe that this is Quentin Tarantino’s most complete screenplay to date. It has a much better all-around story than PULP FICTION and, although it didn’t quite feature the same amount of his signature run-on dialogue, it still had more than enough to please me. Featuring handfuls of languages and subplots, INGLOURIOUS BASTERDS is a complex, ultimately masterful piece of storytelling. It’s far and away my favorite in the category, and even though Mark Boal has won the lion’s share of this year’s awards for THE HURT LOCKER, I think there’s enough Tarantino love out there to secure him a win.

Best Adapted Screenplay

Will Win: Jason Reitman & Sheldon Turner, UP IN THE AIR

Should Win: Jason Reitman & Sheldon Turner, UP IN THE AIR

Nobody writes dialogue as pure and as smooth as Jason Reitman, and his talent is on full-display with UP IN THE AIR. Along with co-writer Sheldon Turner, Reitman continued his unmatched success in creating engaging, multi-layered characters. This fantastic duo has steamrolled through the awards season without any sign of slowing down. Reitman is far too respected and liked to be upset by any of his fellow nominees. He is simply a guy that a lot of people (including me) want to see on that stage.

Best Supporting Actor

Will Win: Christoph Waltz, INGLOURIOUS BASTERDS

Should Win: Christoph Waltz, INGLOURIOUS BASTERDS

Christoph Waltz is an unknown Austrian actor (or was, before this breakout performance) who is responsible for creating one of Quentin Tarantino’s most memorable characters to date. He could have won this thing for the film’s opening scene alone, but fortunately for us, he appears throughout the entire movie in the same irresistible form. I can’t think of many actors who could create so many believable layers while playing a Nazi soldier. A lot of credit is obviously due to Tarantino’s screenplay, as the words Waltz is assigned to say are magic in their own right, but I’m not sure anyone else could have brought this character to life with the same effectiveness. Woody Harrelson’s career-best performance in THE MESSENGER is a deserving runner-up in my book. 

Best Supporting Actress

Will Win: Mo’Nique, PRECIOUS

Should Win: Mo’Nique, PRECIOUS

A category with five impressive nominees is nevertheless the one with the biggest standout. Mo’Nique’s revelatory, pulverizing work as the disturbed mother in PRECIOUS is a work of art. Rarely do we see supporting female characters with such intensity and conviction. Over the course of this tremendous film, she delivers two monologues that could rival some of the decade’s best work. The first one is a screaming, barking rant directed towards her daughter, and the second is an intimate, vulnerable confession directed towards the same woman (as well as Mariah Carey’s social worker). For these two scenes alone, Mo’Nique has put herself on the map as a powerful dramatic performer. The UP IN THE AIR ladies — Anna Kendrick and Vera Farmiga — deserve a mention here, as does Maggie Gyllenhaal for her admirable work alongside Jeff Bridges in CRAZY HEART.

Best Actor

Will Win: Jeff Bridges, CRAZY HEART

Should Win: Colin Firth, A SINGLE MAN

Jeff Bridges’ inevitable Oscar win for his portrayal of “Bad” Blake will be seen as a lifetime achievement award by many, but his work in CRAZY HEART is truly deserving of all of the praise. It may not be his best work ever, but it remains a dazzling, Oscar-worthy performance in every sense of the word. I still think that Colin Firth gave the year’s most impressive all-around performance in A SINGLE MAN, but this is a rare occasion in which I have no problem seeing my personal favorite take a step back. I will be beaming with joy when Bridges finally has that gold statue in his hand. 

Best Actress

Will Win: Sandra Bullock, THE BLIND SIDE

Should Win: Gabourey Sidibe, PRECIOUS

Sandra Bullock is a fine actress, perhaps even an Oscar-worthy one, but to label her work in THE BLIND SIDE as the “Best Actress” of 2009 is stretching it quite a bit. Among the five nominees, only Carey Mulligan can come close to matching the raw power of Gabourey Sidibe’s debut performance in PRECIOUS. The actress does a stunning job conveying the character’s physical attitude, such as the slouched posture and grumbling voice, and she also manages to affect the audience on an emotional level that is unmatched by any other nominee. It is, in my opinion, one of the standout female portrayals of the decade, but for some reason, it is just Bullock’s year.

Best Director

Will Win: Kathryn Bigelow, THE HURT LOCKER

Should Win: Kathryn Bigelow, THE HURT LOCKER

I’m not sure I could put it better than fellow nominee Jason Reitman, when he said of Kathryn Bigelow, “The amount of directorial control in THE HURT LOCKER is second to none. She’s going to win, and she deserves to win.” Bigelow created a war film that was unlike any experience I’ve ever had in that genre before. It doesn’t have a single cliché to speak of, and the director’s ability to create suspense is something that few directors can match. Her ex-husband, James Cameron, warrants a mention here (who else really could have made AVATAR?), but Bigelow simply succeeded in creating a more effective and memorable dramatic experience. One must also not forget that Bigelow did in fact with the Directors Guild Award, which is a rock-solid precursor for predicting who will take home Oscar gold. 

Best Picture

Will Win: THE HURT LOCKER

Should Win: INGLOURIOUS BASTERDS

Best Picture is one of the trickiest categories of the night because it could go to one of three films. Anyone could make a solid, fact-based case for either AVATAR, THE HURT LOCKER, or INGLOURIOUS BASTERDS. The reason I’m going with THE HURT LOCKER is simply because the historical facts are on its side, while they are against a film like AVATAR. Without a screenplay or acting nomination — and without an SAG ensemble nod — the chances of AVATAR winning drop drastically. THE HURT LOCKER also won the Producers Guild of America Award which, although not a perfect indicator, is still another sign pointing in the direction of Kathryn Bigelow’s film. Personally, I think INGLOURIOUS BASTERDS is the most complete motion picture of 2009, but THE HURT LOCKER was #2 on my Top Ten list, so you’ll see no complaints from me if THE HURT LOCKER does in fact take home a well-deserved Oscar.

Thanks, Danny. Readers, how do you feel about Danny’s picks? Did he miss the boat on something? Let us know in the comments.