The Hitchhiker's Guide to the Academy Awards 2026

by Bill Grinnell

The Academy Awards ceremony is the biggest event of the year for me. I actually refer to it as Film Geek Christmas, and yes, as much as I hate to admit it, this day is more important to me than Christmas.

Everything is up in the air this year, and everyone is admitting they have no idea who is going to wing Here are my best guesses for Oscar night 2026:

Best Picture

Undoubtedly the most contentious race of the night. One Battle After Another won the Golden Globe and the Producer’s Guild Award, while Sinners one the Actor Award (formerly known as the SAG Award.) It’s really anyone’s guess, but the edge has to go to One Battle After Another. The only one who has even an outside chance would be Hamnet, assuming voters can get over the constant mumbling of all the actors except Emily Watson.

Best Actor

This one is almost as close as Best Picture. In the end, expect Leonardo DiCaprio to pick up his second Oscar.

Best Actress

If there’s one sure thing all night, it’s this one. It’s a seemingly weak field but in the end it doesn’t affect the outcome. Jessie Buckley has been winning everything and should do so here as well. It’s the one strong performance amongst a weaker field.

Best Supporting Actor

This one’s a little more comfortable as well. Sean Penn will pick up his third Oscar, bringing him into the highly exclusive “actors who have won more than twice” club. It’s a small group and is comprised of Frances McDormand (three best actress), Walter Brennan (three best supporting actor), Ingrid Bergman (two best actress, one best supporting actress), Daniel Day Lewis (three best actor), Meryl Streep (two best actress, one best supporting actress), Jack Nicholson (two best actor, one best supporting actor), and Katharine Hepburn, who actually won four best actress Oscar’s.

Best Supporting Actress

This one is a battle between Amy Madigan and Teyana Taylor. Taylor hasn’t won anything since her Golden Globe win, while Madigan has won many other awards for her performance. Edge: Madigan.

Best Director

It’s not a one hundred percent guarantee that the DGA winner goes on to win the Academy Award, but it’s pretty rare if they don’t. In keeping with that, it’s pretty likely that Paul Thomas Anderson will win for One Battle After Another, having won the coveted DGA Award last week. If anyone were to unseat him, the universal consensus is that Coolger would be the one to do it.