Today begins a new blog series where I’m looking back at five of the major Oscar categories from 1990 to the present: the four acting races and Best Picture. This is essentially the time period where I’ve closely watched and analyzed. My charge? Picking the three largest upsets in each said category and the three least surprising winners… a film or performer where it truly would have been a shock if they didn’t emerge victorious.

We begin with Best Supporting Actress and this is one in which there have been some genuine upsets over the past quarter century plus. Unlike some other races we’ll get to later, it was not a challenge to pick three unexpected winners.

The other agenda item here is I’m picking my personal selections for strongest and weakest overall field among the five nominees in the acting derby’s and five-ten for Best Picture.

For starters, here’s the list of women that won gold statues in the supporting race from 1990 to now:

1990 – Whoopi Goldberg, Ghost

1991 – Mercedes Ruehl, The Fisher King

1992 – Marisa Tomei, My Cousin Vinny

1993 – Anna Paquin, The Piano

1994 – Dianne Wiest, Bullets Over Broadway

1995 – Mira Sorvino, Mighty Aphrodite

1996 – Juliette Binoche, The English Patient

1997 – Kim Basinger, L.A. Confidential

1998 – Judi Dench, Shakespeare in Love

1999 – Angelina Jolie, Girl, Interrupted

2000 – Marcia Gay Harden, Pollock

2001 – Jennifer Connelly, A Beautiful Mind

2002 – Catherine Zeta-Jones, Chicago

2003 – Renee Zellweger, Cold Mountain

2004 – Cate Blanchett, The Aviator

2005 – Rachel Weisz, The Constant Gardner

2006 – Jennifer Hudson, Dreamgirls

2007 – Tilda Swinton, Michael Clayton

2008 – Penelope Cruz, Vicky Christina Barcelona

2009 – Mo’Nique, Precious

2010 – Melissa Leo, The Fighter

2011 – Octavia Spencer, The Help

2012 – Anne Hathaway, Les Miserables

2013 – Lupita Nyong’o, 12 Years a Slave

2014 – Patricia Arquette, Boyhood

2015 – Alicia Vikander, The Danish Girl

2016 – Viola Davis, Fences

2017 – Allison Janney, I, Tonya

I’ll begin with the least surprising winners. Truthfully, there are plenty of selections (and will be in each race) to pick from here. It’s normal procedure for the front runner to actually win. Here’s three that did just that:

3. Dianne Wiest, Bullets Over Broadway

Of the 28 recipients to choose from, note that 3 of them were under the direction of Woody Allen. None were surprise winners. That’s most evident with Wiest’s showcase work as an aging diva here. Her win here came just eight years following her Oscar winning role in another Allen pic, Hannah and Her Sisters.

2. Jennifer Hudson, Dreamgirls

Fans of the Broadway play this is based upon knew Ms. Hudson could have a legitimate breakthrough part here. She nailed it and her win was never in much doubt.

1. Anne Hathaway, Les Miserables

Similar to Hudson’s victory, Hathaway’s casting as Fantine and her “I Dreamed a Dream” dramatic solo made her the odds-on favorite from the moment the project was announced. That never changed.

Now we get to the upsets and there were four to choose from. I could easily include Anna Paquin in The Piano, who became the second youngest winner when she beat out favorite Winona Ryder for The Age of Innocence. Here’s 3 I rank as even more surprising:

3. Marcia Gay Harden, Pollock

Harden had won no significant precursors and Kate Hudson was expected to have her name called for Almost Famous. She wasn’t even nominated for a Golden Globe or SAG.

2. Juliette Binoche, The English Patient

While the film itself was the anticipated winner for Picture (which it did), the Oscars were expected to select the legendary Lauren Bacall for her work in Barbra Streisand’s The Mirror Has Two Faces. Yet it was Binoche’s performance that was unexpectedly honored.

1. Marisa Tomei, My Cousin Vinny

For starters, comedic roles are rarely nominated and wins are even more unheard of. Tomei was a newcomer in a picture that wasn’t a factor in any other category. Her competition was a list of venerable actresses: Judy Davis (Husbands and Wives), Joan Plowright (Enchanted April), Vanessa Redgrave (Howards End), and Miranda Richardson (Damages). The victory here was so shocking that conspiracy theories emerged that presenter Jack Palance had accidentally read the wrong name. That’s been debunked, but Tomei’s trip to the stage remains one of Oscar’s largest jaw droppers.

As for the fields, I’m going with 1991 for the weakest link in the chain. I probably would have given the award to Juliette Lewis in Cape Fear. However, the group was not particularly strong:

Mercedes Ruehl, The Fisher King (Winner)

Diane Ladd, Rambling Rose

Juliette Lewis, Cape Fear

Kate Nelligan, The Prince of Tides

Jessica Tandy, Fried Green Tomatoes

For the strongest field overall, I went with 2004 when Cate Blanchett won for her portrayal of Katherine Hepburn in Martin Scorsese’s The Aviator. The other nominees:

Laura Linney, Kinsey

Virginia Madsen, Sideways

Sophie Okonedo, Hotel Rwanda

Natalie Portman, Closer

And there you have it! I’ll have Supporting Actor up soon…