Watching the Oscars has always been one of my greatest guilty pleasures. I love everything about the evening, from chuckling with Joan and Melissa as they dish the dirt live on the red carpet to watching weepy celebrities–dressed in clothes that cost more than many of us make in a year–give ridiculously long acceptance speeches. I’ve also won more than one office betting pool by correctly picking all of the winners in all of the major categories. So I am putting my self-proclaimed Oscar savvy on the line by blogging my predictions, as well as my personal picks, so I can be applauded (or ridiculed, if the case warrants) right here at a later date. And don’t forget you can also read about or discuss many of the Oscar-nominated movies over at the Beliefnet Film Awards.

Leading Actor
The nominees: Philip Seymour Hoffman (“Capote”); Terrence Howard (“Hustle & Flow”); Heath Ledger (“Brokeback Mountain”); Joaquin Phoenix (“Walk The Line”); David Strathairn (“Good Night, and Good Luck”)

My analysis: This is one category “Brokeback” is definitely not going to win. Philip Seymour Hoffman’s portrayal of eccentric author Truman Capote is Hoffman’s best and, perhaps only, chance to win an Oscar. He won this category at the Screen Actor’s Guild Awards, which is always a good indicator of who will win on Oscar night. However, this is an extremely competitive category and both Terrence Howard and David Strathairn are well-respected actors who have a chance at pulling off a surprise win.

Who will win: Philip Seymour Hoffman

Who should win: Terrence Howard for giving two completely different yet equally amazing performances (the other one was in “Crash”) last year.

Leading Actress
The nominees: Judi Dench (“Mrs. Henderson Presents”); Felicity Huffman (“Transamerica”);
Keira Knightley (“Pride & Prejudice”); Charlize Theron (“North Country”); Reese Witherspoon (“Walk the Line”)

My analysis: The only questions here are whether enough of the Academy saw “Trasmamerica” to vote for Huffman, and whether the Academy views Huffman as a real feature film actress or simply that lady from “Desparate Housewives” who did an indie film with her husband.

Who will win: Reese Witherspoon, because she is a major movie star whose career is on the rise, and the Academy will want to celebrate that.

Who should win: Reese Witherspoon, but only because this is actually a weak category this year, and I was not a fan of “Transamerica.”

Supporting Actor
The nominees: George Clooney (“Syriana”); Matt Dillon (“Crash”); Paul Giamatti (“Cinderella Man”); Jake Gyllenhaal (“Brokeback Mountain”); William Hurt (“A History of Violence”)

My analysis: This category is another close three-way horse race between Matt Dillon, George Clooney, and Paul Giamatti. Each has won at least one award for their performances during the pre-Oscar award season. Many critics think that since Clooney has three different Oscar nominations, the Academy will be sure to give him at least one award, and this will be the category to do it in.

Who will win: Matt Dillon, because I think Clooney will win an Oscar in a different category, and Dillon played the best anti-hero on screen in years.

Who should win: Paul Giamatti , because he has given so many consistently impressive performances over the last few years, with “Cinderella Man” showcasing his best work ever.

Supporting Actress
The nominees: Amy Adams (“Junebug”); Catherine Keener (“Capote”); Frances McDormand (“North Country”); Rachel Weisz (“The Constant Gardner”); Michelle Williams (“Brokeback Mountain”)

My analysis: While Michelle Williams’s performance in “Brokeback” was truly heart-wrenching, Hollywood doesn’t seem to be ready to give her credit where credit is due just yet. Therefore, the focus has been solely on Rachel Weisz for her performanceas an activist who is murdered in “The Constant Gardner.”

Who will win: Rachel Weisz, because she has won every other award this season, and it is a way for the Academy to recognize what a good film “The Constant Gardner” was.

Who should win: Amy Adams , because “Junebug” deserves some kind of nod from Oscar and her performance was touching and hilarious at the same time.

Best Picture
The nominees: “Brokeback Mountain”; “Capote”; “Crash”; “Good Night, and Good Luck”; “Munich”

Who will win: “Brokeback Mountain,” partially because it will get shut out in the acting categories and partly because Hollywood loves to make “statements.”

Who should win: If you have been reading my entries here at Idol Chatter at all, you already know that I think “Crash” is by far the best movie of last year, and I am still rooting for it to pull an upset win.