How many times have both Best Actor and Best Supporting Actor gone to the same film at the Oscars?

Three films in contention at this year’s Oscars earned nominations for both Best Actor and Best Supporting Actor: “Green Book,” “A Star is Born” and “Vice.” How likely is it that both these men from the same film will win Academy Awards on Feb. 24? In the 82 years since the supporting awards were introduced at the 9th Oscars, only five films could boast victories in both these races.

For such a male-dominated industry, it is surprising that these two acting categories are the least successful pairing at the Oscars while the two female ones are the most. Then again, the film industry has no shortage of roles for men (lead or supporting) so they have been able to spread the love across different male performers in different films. There has always been (and still is) a shortage of female roles, so there have been and are fewer films with such notable performances, be they lead or supporting.

The five films to pull off this double act were:

Barry Fitzgerald and Bing Crosby for “Going My Way” – 1944
Harold Russell and Fredric March for “The Best Years of Our Lives” – 1947
Hugh Griffith and Charlton Heston for “Ben-Hur” – 1960
Tim Robbins and Sean Penn for “Mystic River” – 2004
Jared Leto and Matthew McConaughey for “Dallas Buyers Club” – 2014

PREDICT the Oscar winners now; change them until Feb. 24

Here are are the three pairings that could join them in the Oscar history books: 

Sam Elliot and Bradley Cooper – “A Star is Born”
Mahershala Ali and Viggo Mortenson – “Green Book”
Sam Rockwell and Christian Bale – “Vice”

The likeliest of these to both win Oscars is the pair from “Green Book.” Ali is odds on favorite to win his second Supporting Actor following his win in 2017 for “Moonlight.” However, Mortensen would have to get past the heavily favored “Bohemian Rhapsody” leading man Rami Malek, who has won the Golden Globe, SAG, and BAFTA as well as Christian Bale, who won the Critics’ Choice award.

Be sure to make your Oscar predictions so that Hollywood insiders can see how their films and performers are faring in our odds. You can keep changing your predictions until just before winners are announced on Feb. 24. And join in the fierce debate over the 2019 Oscars taking place right now with Hollywood insiders in our movie forums. Read more Gold Derby entertainment news.

SIGN UP for Gold Derby’s free newsletter with latest predictions

More News from GoldDerby