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  • Rough Cut Staff

Mailbag, Part 2: The Best in Oscars History

It's Oscars Month, so our writers are answering the most burning questions about the Academy Awards. In part 1, they took on the upcoming 93rd Oscars. Today, they dive into the history of the most prestigious award show of the year.

Buena Vista

1. What is the most memorable Oscars ceremony opening number? If and when you select Hugh Jackman at the 81st Academy Awards, please also pick an alternate.

ZD: I lean more toward strong stand-up than show-stopping performance, and nobody did it better than Chris Rock in ’05.

SMD: I would say Johnny Carson’s 1980 monologue. I’m sure I only get about half of the jokes and I still think it’s the best. Hugh Jackman (2009) and Chris Rock (2016) are honorable mentions.

CC: I watch the Jackman number at least once a month, but I’ll go with his Tony buddy NPH’s 2015 gig as a solid runner-up.

JD: Thank you for acknowledging that the Hugh Jackman Oscars opening is the obvious and correct answer. But if I have to pick another one, here are my criteria: the ideal Oscars opening is by someone with movie star charisma and legit performance chops, celebrates the movies of the year in some way, and provides the ceremony with an upbeat, high-energy kickoff. The Academy had the fortunate chance to do all those things and check off one of their Best Original Song performances at the same time when Justin Timberlake began the 89th Oscars Ceremony with “Can’t Stop the Feeling.” Look how much fun everyone is having!

2. If you could add one Oscar category, and only one, what would it be?

ZD: Casting!! We experience most movies through their characters, and casting directors have to navigate not only talent and fit, but also the impact of the public’s relationship with any given actor.

SMD: Second-Best Picture.

CC: If I can only pick one? It’s wild to me that we aren’t recognizing stunt performers yet – I worry that we’re hurtling towards a world where CGI makes practical stunt work obsolete, so we should reward stunt crews while we can (plus those nominee clip packages would sure be fun to see).

JD: It is frankly bananas that casting directors are not honored at the Oscars, and it probably has more than a little bit to do with the fact that historically casting was one of the few film disciplines that heavily employed women. Fix this, Academy.

3. Pick your favorite and least favorite Oscar winners, any category, in the last 10 years.



Favorite: I think 2016 saw the best pair of screenplays to ever win – Moonlight for Adapted and Manchester by the Sea in Original.

Least Favorite: Bohemian Rhapsody for Film Editing is probably the worst. But the one that cuts me to my core is Frances McDormand’s Best Actress win for Three Billboards Outside Ebbing, Missouri. She’s a phenomenal actor, but that’s one of her worst performances, and to win a second Oscar for it – especially over Saoirse Ronan’s magical turn in Lady Bird – is a huge bummer.


Favorite: Parasite, Best Picture

Least Favorite: Green Book, Best Original Screenplay


Favorite: It’s hard to understate how exciting last year’s Parasite Best Picture win was. Does the fact that it was one of the last few good things to happen pre-COVID factor into this? Probably – but it doesn’t matter, it’ll likely stand as one of the coolest Oscar moments for some time.

Least Favorite: There are definitely worse winners over the past decade (Green Book, Rami Malek, etc.), but I’m not sure I was ever more disappointed than I was with Gary Oldman’s Darkest Hour win. It’s a fine movie and a fine piece of acting, but the fact that the Academy went with “historical figure, lots of makeup” over four other really interesting performances (from Chalamet, Day-Lewis, Kaluuya, and Washington) is deeply depressing.


Favorite: Awarding a Best Picture Oscar to Parasite is one of the coolest things the Academy has ever done.

Least Favorite: Giving Alejandro González Iñárritu a second consecutive Best Director Oscar for The Revenant was already entirely unnecessary, but what really pushes it over the line is that the Academy could have instead given it to George Miller for Mad Max Fury Road. But I guess that would have been too rad.

4. You can only watch three movies for the rest of your life, and they all have to be Best Picture winners. Which three do you choose?


Parasite: I’ve seen it three times in 18 months and it hasn’t gotten old. True genius.

The Apartment: There’s so much layered into this by Billy Wilder that I could watch it 100 times and notice something new on each watch.

Casablanca: It makes me happy.


The Sting

The Lord of the Rings: The Return of the King



A tough question – I think I might have an easier time picking the best as opposed to this, the most rewatchable – and one where my answer probably changes by the day, but in this pseudo-desert island scenario, I’m going with My Fair Lady, Amadeus, and Gladiator.


Casablanca, West Side Story, and Moonlight are three of my favorite movies of all time. What can I say? I’m a sucker for romance.

Warner Bros

5. Oscar Genie: If you could make one change in Oscars history that you believe would lead to a domino effect, what would it be? And how would that change Oscars history?


Alright, here’s what will do.

It bums me out that Lauren Bacall never won an acting Oscar. She was nominated once – so she has to win for 1996’s The Mirror Has Two Faces. But that takes the trophy away from the great Juliette Binoche in The English Patient, and she obviously needs an Oscar. She was nominated once more, in 2000’s Chocolat. We’ll give her the win, but oh no! That steals Julia Roberts’ only Oscar, for Erin Brockovich. She’s only been nominated one time since 2000: Best Supporting Actress for 2013’s August: Osage County. In a real bummer turn of events, the Academy gives her the now long overdue Oscar over Lupita Nyong’o in 12 Years a Slave.

But wait! After that terrible slight, the Academy makes up for it by nominating Lupita and giving her the trophy for 2019’s Us. The only person who truly suffers is Renée Zellweger, who didn’t need the second Oscar she won for Judy, anyway.


Let’s start in 1987. Moonstruck loses the award for best original screenplay (it also doesn’t win best picture or best director and – relevant here – Nicolas Cage was not nominated). It’s important to me that this happens, because the screenplay is not that great. Really. Try me.

Moonstruck therefore only gets two acting awards (Cher and Olympia Dukakis) and not as many accolades in the press. (In case you’re wondering, the Best Original Screenplay award instead goes to Broadcast News).

Without that extra boost, Nicolas Cage does not get cast in Leaving Las Vegas. He’s left to flounder on the sidelines of Hollywood stardom for the rest of his career. Naturally, that means he doesn’t get nominated for the 1995 Oscar awards ceremony (the year in which Leaving Las Vegas was eligible). Instead, Massimo Troisi is given a posthumous Oscar for his role in Il Postino: The Postman. Troisi died 12 hours after main filming for that movie ended, by the way. It’s literally one of the last things he ever did. Italy cries in appreciation for the Academy’s benevolence and recognition of a beloved star.

That also means that in 2002, Richard Gere gets nominated for Best Actor in Chicago (instead of Nicolas Cage in Adaptation). Gere doesn’t win – he’s up against Adrian Brody in The Pianist, for god’s sake – but how nice for him to finally be recognized by the Academy.



Give Joaquin Best Actor for The Master in 2013. Daniel Day Lewis misses out here, picking up his third Oscar for Phantom Thread instead, which is more fun anyway. Oldman loses to DDL and subsequently gets nothing (sorry Gary, you’re not winning for Mank). Joaquin’s career goes in a slightly different direction after his win, and he doesn’t bother making Joker, which means we just don’t have to deal with or think about that movie. Warner Bros. Leans even more heavily into the Wonder Woman / Shazam / Aquaman brand of DC movies instead of the grim and gritty, and continues to ignore the Snyder Cut truthers. The internet enters a new golden age where people are only nice to each other. Democracy is saved.


In 1972, Marlon Brando won his second Best Actor Oscar for The Godfather, while his co-star Al Pacino was bumped down to supporting alongside castmates James Caan and Robert Duvall. Let’s say that Pacino had rightfully joined his onscreen father in lead and won his Oscar at the cusp of his unparalleled 70s run, instead of waiting until the 90s to win for a much lesser performance in Scent of a Woman. Let’s also say that with less internal competition, Duvall manages to consolidate the Godfather vote and defeats Joel Grey. Those two moves create a waterfall that will reverberate for decades.

Let’s start with Duvall. With a win under his belt for The Godfather, he doesn’t need a second for 1983’s Tender Mercies. Instead, Michael Caine wins in 1983 for Educating Rita. Having just awarded him so recently, the Academy doesn’t need to give him another so soon for Hannah and Her Sisters in 1986, so Willem Dafoe can win instead for Platoon. And let’s just go ahead and give Caine’s second win in 1999 to Tom Cruise for Magnolia instead.

Meanwhile, Pacino’s alternate-universe 1972 Best Actor win clears the field for Denzel Washington to win his lead acting Oscar in 1992 for his career-best performance in Malcolm X. That then opens up the 2001 race, which realistically probably leads to Russell Crowe winning back-to-back Oscars for Gladiator and A Beautiful Mind. But it’s more fun to think about what would happen if Sean Penn instead wins a truly cursed Oscar for I am Sam. The ensuing backlash probably means no wins for Penn in 2003 and 2008, letting Bill Murray triumph in 2003 for Lost in Translation. In this alternate universe, Mickey Rourke still falls short in 2008, losing to Brad Pitt in The Curious Case of Benjamin Button. With a lead Oscar already under his belt, Brad doesn’t have to drop down to supporting for Once Upon a Time in Hollywood, and instead campaigns alongside Leo in lead. That opens up a spot in the 2019 supporting actor field for Song Kang-ho in Parasite to swoop in and take the gold. You’re welcome.


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