The main downside that comes with betting on the Oscars is the subsequent desire to watch the damn thing. Three tedious hours of self-congratulation from the richest and most beautiful people on earth (with occasional lashings of purported victimhood, such as Meryl Streep speaking of Hollywood celebrities when she said: “[we] belong to the most vilified segment of American society”)
But a bet is a great way to focus the mind, an aphrodisiac for the attention. So, yes, I will be gripping the arms of my TV chair as the Academy Award for Best Sound Mixing is announced, I can assure you.
A few points before I make my tips. This is the fourth consecutive year I’ve bet on the Oscars. I’ve made a profit the previous three years. I rarely watch the movies in question, as quality of film is not particularly important in determining the winner, and my personal opinion is utterly irrelevant. The four main factors that are relevant are:
First: The current political climate (that is, what choice of winner will suit this particular moment of hyper-partisan toxic politics in the United States).
Second: The likely choices of Academy members – that is, the limousine liberals of Hollywood – based on the aforementioned political climate.
Third: The ground game of the movies and actors. That is, how much money the studio has spent campaigning (Netflix is rumoured to have spent 50 million dollars on pushing Roma to get as many awards as possible, which is more than three times the cost of the actual movie), and how well individual actors have campaigned (Rami 
Malek – star of Bohemian Rhapsody – has been showing up at every party in Hollywood, and is apparently well-liked by all who meet him).
This ground game – like any good political campaign – also involves dirty tricks, so negative stories associated with the major films have to be taken into account. Both Bohemian Rhapsody and Green Book have controversies associated, for example.
Fourth: Quality of the film. This is the least important aspect. Usually, decently-reviewed films will get into the Best Picture category (though Bohemian Rhapsody is only 60% currently on Rotten Tomatoes); however, when it comes to choosing the winner from the finalists, this factor rarely comes into play.
Cynical? Oh my, oh yes; but money is involved here: this isn’t what should be, dear punter, this is simply what it is.
Without further ado, my bets:
Best Picture:
Green Book @ $4.33.
Roma will probably win, but I don’t believe it is as strong a favourite as current betting ($1.30). The questions is this: do Academy voters really want to give Alfonso Cuaron Best Director, Best Foreign Film, and Best Cinematography (and they will), and on top of that give him Best Film as well? For a Netflix production?
Best Original Screenplay:
The Favourite. I got on this @ $1.94 and $3.24. It is currently in to $1.50.
The Favourite is a well-liked film that Academy voters will want to give a major award to.
Special Effects:
First Man @$4.33
Avengers is currently favourite at $1.25. However, among the people with expertise in this field, the word is First Man is quite extraordinary. The question is whether the Academy will give the award to best special effects, or most special effects. Avengers will win if the latter is the case.
Watch out for: Spike Lee.
He is overdue an Oscar. He probably should have won for Do The Right Thing thirty years ago. He’ll win Best Adapted Screenplay this time around for certain, but he is an outside chance for Director, should the academy think Spike is due, and Alfonso has won enough already (he’s won two Academy awards previously, will win at least two to four more for Roma – Cinematography and Foreign Film being locks).
Watch out for: Best Supporting Actress
I think there will be an upset in this category.
Regina King is @ $1.33. Amy Adams, @ $6.00, has been nominated 6 times for no wins, and some may feel it is her turn. Rachel Weisz, @ $7.00, won the BAFTA, and is well-liked in the industry. The pricing on this market does not look right to me.
I have many more bets, which I won’t regale you with. Just to say that I tend not to bet on the favourites in any category, rather going for mispriced outsiders.
The one exception last year was when I bet big on Roger Deakins for Cinematography on Blade Runner 2049 (which he 
won), and the exception this year are my bets on The Favourite for Screenplay.
Predictions:
Film: Roma
Director: Alfonso Cuaron
Actress: Glenn Close
Actor: Rami Malek
Supporting Actor: Mahershala Ali
Supporting Actress: Rachel Weisz
Best Original Screenplay: The Favourite
Best Adapted Screenplay: BlacKkKlansman
Cinematography: Roma
Original Song: Shallow – A Star is Born
Original Score: If Beale Street Could Talk
Documentary Short: End Game
Documentary feature: Free Solo
Live Short Action: Marguerite
Foreign Language: Roma
Animated Feature: Spider-Man: Into the Spider-Verse
Animated Short: Weekends
Visual Effects: First Man
Film Editing: Vice
Production Design: The Favourite
Costume Design: Black Panther
Makeup and Hair: Vice
Sound Mixing: Bohemian Rhapsody
Sound Editing: Bohemian Rhapsody