We begin our daily Oscar predictions coverage with the Best Supporting Actress category. Each day between now and the Friday before the Academy Awards, we here at CinemaSight will be presenting a category-by-category analysis of the races including trivia about the category, our predictions and alternates, and a glimpse out our favorite and least favorite winners in each category.

Trivia: Five Facts

• First introduced for the 9th Academy Awards representing the best of film in 1936, Gale Sondergaard became the first winner of this category.
• Only two actresses have won the award twice: Shelley Winters in 1959 and 1965; and Dianne Wiest in 1986 and 1994.
• Beatrice Straight holds the record for the shortest performance to win the award appearing on screen for a mere 5 minutes, 40 seconds.
• Linda Hunt is the only actress to win the prize for playing a man.
• The actress who wins this year will be taking home the category’s 74th prize, but only 66 of them received Academy Award statuettes. Until 1943, Supporting category winners received plaques and not statuettes.

Predictions

• Penélope Cruz – Nine
• Vera Farmiga – Up in the Air (Wesley, Tripp)
• Maggie Gyllenhaal – Crazy Heart
• Anna Kendrick – Up in the Air (Peter, Wes)
• Mo’Nique – Precious (Wesley, Peter, Tripp, Wes)

KEY: (Winner Prediction) (Alternate Winner)

The Commentary

Wesley Lovell – For once I feel confident about a runaway critics’ awards winner taking the Oscar. It’s not always a sure thing, just ask Amy Ryan who lost to Tilda Swinton after taking 14 precursor prizes. The difference here is that Mo’Nique not only picked up the Golden Globe when Ryan didn’t, but also got the SAG award, which went to sentimental Ruby Dee. The only precursor that hasn’t weighed in that could impact this prediction is BAFTA, the first group in 2007 to pick Tilda Swinton, which started the ball rolling towards her Oscar victory. Vera Farmiga seems like one of those actress that Oscar voters might like to honor for a quiet build up of a strong career. Penelope Cruz already won and Anna Kendrick is a bit too new to the world of film acting. Maggie Gyllenhaal, on the other hand, is a lot like Farmiga and could benefit equally from Academy sentiments.
Peter J. Patrick – Kendrick will come closest, but Mo’Nique has it in the bag.
Tripp Burton – This year has been dominated by Mo’Nique so far, and I have a hard time seeing her losing any steam here. It is the sort of bold, brash character that this category loves to honor, and her story from talk show host/comedian to dramatic tour de force is too much to resist. Everyone else will have to settle for the honor of being nominated.

Our Favorite Winners

KEY:
Appears on Two Lists
Appears on Three Lists
Appears on Four Lists
Appears on Opposing Lists

Wesley Lovell

There are more supporting performances I enjoy than I hate, which is surprising. Whoopi Goldberg, Shelley Winters, Jennifer Hudson and Angelina Jolie are all interesting, but my five simply cannot be so easily surpassed.

1. Dianne Wiest – Bullets Over Broadway (Wiest is incomparable in possibly the most deliciously hilarious role in the category’s history.)
2. Jo Van Fleet – East of Eden (Van Fleet gives a courageous, in depth performance that resonates long after the film itself fades from memory.)
3. Estelle Parson – Bonnie and Clyde (Estelle Parson is hysterically good in a scenery-chewable showcase that doesn’t feel too soggy.)
4. Cate Blanchett – The Aviator (Cate Blanchett gets impeccably deep into Kathrine Hepburn’s skin.)
5. Celeste Holm – Gentleman’s Agreement (Celeste Holm had a circumstantial role in Gentleman’s Agreement, but still managed to deliver a funny, memorable turn.)

Peter J. Patrick

1. Jane Darwell – The Grapes of Wrath (Darwell infused her portrayal of the indomitable Mother Ma Joad with an equal measure of intensity and warmth to create one of the most unforgettable screen characters of all time.)
2. Ruth Gordon – Rosemary’s Baby (Gordon’s delectable witch next door bearing gift remains the screen’s supreme example of benign horror. )
3. Eileen Heckart – Butterflies Are Free (Heckart is hilarious as the overbearing mother who is a match for her detractors all the while learning to let go of her handicapped son despite grave misgivings.)
4. Ingrid Bergman – Murder on the Orient Express (the biggest name in an all-star cast takes a tiny part and spins it into pure gold with the sheer force of her presence.)
5. Ethel Barrymore – None but the Lonely Heart

(Barrymore brings a lifetime of great stage acting to a new medium and shows the experts how it’s really done.)

Tripp Burton

1. Dianne Wiest – Hannah and Her Sisters (Wiestgives a tender, lovely performance, and is able to walk the fine line between a broad character and a real tormented human being perfectly. Her later win may be more fun, but this is much deeper.)
2. Jane Darwell – The Grapes of Wrath (A strong, hearty performance that lies at the center of this masterwork.)
3. Mary Steenburgen – Melvin and Howard (The fact that Steenburgen has never been given a role this fun and meaty again is a shame. She may seem like a one-hit wonder these days, but what a hit it was.)
4. Estelle Parson – Bonnie and Clyde (This category often awards big, bold choices (they love hysterics) as Mo’Nique’s impending win goes to show. No one did that better than Estelle Parsons, i.e. no one made those choices seem so real and grounded.)
5. Beatrice Straight – Network (As this category goes more and more to secondary lead roles and big, A-List stars, it is more and more a wonder that Straight was able to win for this small, important and meaningful role. That scene is astonishing!)

Wes Huizar

1. Eva Marie Saint – On the Waterfront
2. Hattie McDaniel – Gone With the Wind
3. Ruth Gordon – Rosemary’s Baby
4. Patty Duke – The Miracle Worker
5. Jennifer Hudson – Dreamgirls

Our Least Favorite Winners

KEY:
Appears on Two Lists
Appears on Three Lists
Appears on Four Lists
Appears on Opposing Lists

Wesley Lovell

1. Jennifer Connelly – A Beautiful Mind (Connelly was devastatingly good in Requiem for a Dream, but her performance in A Beautiful Mind is cloying and inauthentic.)
2. Donna Reed – From Here to Eternity (Reed was barely in her film and nothing in her work was even remotely interesting.)
3. Kim Basinger – L.A. Confidential (Basinger won for a rather weak, shallow impersonation of Veronica Lake.)
4. Judi Dench – Shakespeare in Love (Dench’s work lacks substance, importance and feels simply like a make up award for losing for Mrs. Brown.)
5. Jessica Lange – Tootsie (Lange doesn’t even give the best performance in her film.)

Peter J. Patrick

1. Angelina Jolie – Girl, Interrupted (After showing remarkable talent in the TV movies George Wallace and Gia, Jolie chews the scenery in her first major screen role, clearly an example of the Oscar going to the nominee who did the “most” acting, not the best.)
2. Gloria Grahame – The Bad and the Beautiful (Great actress, mediocre performance and one so brief, if you take a bathroom break the minute before she appears you’ll miss the whole thing.)
3. Penelope Cruz – Vicky Cristina Barcelona (A lot of screeching in two languages. I don’t get the fascination.)
4. Gale Sondergaard – Anthony Adverse (Marvelous actress but a nothing part and hardly the best choice for Oscar’s first win in this category.)
5. Renee Zellweger – Cold Mountain (Warmed over Marjorie Main or was it Judy Canova? Deserving of a nomination in a weak year, but hardly a win.)

Tripp Burton

1. Catherine Zeta-Jones – Chicago (One of the most lifeless, uninspired turns in a musical I can remember. This is a role based on verve and fire, and Zeta-Jones has none of that.)
2. Renee Zellweger – Cold Mountain (The complete opposite of Parson’s wonderful turn is this, where every big choice comes across fake and shallow.)
3. Rachel Weisz – The Constant Gardener (This category honors a lot of bland performances by gorgeous women, and this is one of the most uninteresting of them.)
4. Goldie Hawn – Cactus Flower (See Rachel Weisz.)
5. Helen Hayes – Airport (It is hard to begrudge an Oscar for one of the greatest American actresses, but she doesn’t do much to deserve it for this film.)

Wes Huizar

1. Renee Zellweger – Cold Mountain
2. Jennifer Connelly – A Beautiful Mind
3. Helen Hayes – Airport
4. Rita Moreno – West Side Story
5. Whoopi Goldberg – Ghost